2855:
diseases because regulatory T cells have a central role in the suppression of inflammatory and allergic responses. In several research studies, it has been demonstrated that butyrate induced the differentiation of regulatory T cells in vitro and in vivo. The anti-inflammatory capacity of butyrate has been extensively analyzed and supported by many studies. It has been found that microorganism-produced butyrate expedites the production of regulatory T cells, although the specific mechanism by which it does so unclear. More recently, it has been shown that butyrate plays an essential and direct role in modulating gene expression of cytotoxic T-cells. Butyrate also has an anti-inflammatory effect on neutrophils, reducing their migration to wounds. This effect is mediated via the receptor
2843:. In particular, circulating butyrate prompts the generation of extrathymic regulatory T cells. The low-levels of butyrate in human subjects could favor reduced regulatory T cell-mediated control, thus promoting a powerful immuno-pathological T-cell response. On the other hand, gut butyrate has been reported to inhibit local pro-inflammatory cytokines. The absence or depletion of these BPB in the gut could therefore be a possible aide in the overly-active inflammatory response. Butyrate in the gut also protects the integrity of the intestinal epithelial barrier. Decreased butyrate levels therefore lead to a damaged or dysfunctional intestinal epithelial barrier. Butyrate reduction has also been associated with
454:
266:
43:
1080:
1384:, a French chemist, was also researching the composition of butter and was publishing his findings and this led to disputes about priority. As early as 1815, Chevreul claimed that he had found the substance responsible for the smell of butter. By 1817, he published some of his findings regarding the properties of butyric acid and named it. However, it was not until 1823 that he presented the properties of butyric acid in detail. The name butyric acid comes from
59:
33:
1005:
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2824:. This is characterized by an overall low biodiversity and a depletion of key butyrate-producing members. Butyrate is an essential microbial metabolite with a vital role as a modulator of proper immune function in the host. It has been shown that children lacking in BPB are more susceptible to allergic disease and Type 1 Diabetes. Butyrate is also reduced in a diet low in
4774:
epigenetic regulators of gene expression by the inhibition of histone deacetylase (HDAC). Recent evidence suggests that dietary fiber and the gut microbial-derived SCFAs exert multiple beneficial effects on the host energy metabolism not only by improving the intestinal environment, but also by directly affecting various host peripheral tissues.
1081:
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astrocytes . ... SLC5A8 is expressed in normal colon tissue, and it functions as a tumor suppressor in human colon with silencing of this gene occurring in colon carcinoma. This transporter is involved in the concentrative uptake of butyrate and pyruvate produced as a product of fermentation by colonic bacteria.
3036:. It produces different effects in healthy and cancerous cells: this is known as the "butyrate paradox". In particular, butyrate inhibits colonic tumor cells and stimulates proliferation of healthy colonic epithelial cells. The explanation why butyrate is an energy source for normal colonocytes and induces
4773:
Short-chain fatty acids (SCFAs) such as acetate, butyrate, and propionate, which are produced by gut microbial fermentation of dietary fiber, are recognized as essential host energy sources and act as signal transduction molecules via G-protein coupled receptors (FFAR2, FFAR3, OLFR78, GPR109A) and as
3137:
in the gut) could be effective by replenishing butyrate levels. In this treatment, a healthy individual donates their stool to be transplanted into an individual with dysbiosis. A less-invasive treatment option is the administration of butyrate—as oral supplements or enemas—which has been shown to be
2819:
Butyrate is essential to host immune homeostasis. Although the role and importance of butyrate in the gut is not fully understood, many researchers argue that a depletion of butyrate-producing bacteria in patients with several vasculitic conditions is essential to the pathogenesis of these disorders.
5066:
Monocarboxylate transporters (MCTs) are known to mediate the transport of short chain monocarboxylates such as lactate, pyruvate and butyrate. ... MCT1 and MCT4 have also been associated with the transport of short chain fatty acids such as acetate and formate which are then metabolized in the
2621:
will be unable to access regions where histones are tightly associated with DNA (i.e., non-acetylated, e.g., heterochromatin). Therefore, butyric acid is thought to enhance the transcriptional activity at promoters, which are typically silenced or downregulated due to histone deacetylase activity.
5010:
Other in vivo studies in our laboratories indicated that several compounds including acetate, propionate, butyrate, benzoic acid, salicylic acid, nicotinic acid, and some β-lactam antibiotics may be transported by the MCT at the BBB. ... Uptake of valproic acid was reduced in the presence of
2854:
In a 2013 research study conducted by
Furusawa et al., microbe-derived butyrate was found to be essential in inducing the differentiation of colonic regulatory T cells in mice. This is of great importance and possibly relevant to the pathogenesis and vasculitis associated with many inflammatory
2866:
In the gut microbiomes found in the class
Mammalia, omnivores and herbivores have butyrate-producing bacterial communities dominated by the butyryl-CoA:acetate CoA-transferase pathway, whereas carnivores have butyrate-producing bacterial communities dominated by the butyrate kinase pathway.
1079:
4957:
the middle and inferior rectal veins drain the lower part of the rectum and venous blood is returned to the inferior vena cava. Therefore, drugs absorbed in the latter system will be delivered preferentially to the systemic circulation, bypassing the liver and avoiding first-pass
3138:
very effective in terminating symptoms of inflammation with minimal-to-no side-effects. In a study where patients with ulcerative colitis were treated with butyrate enemas, inflammation decreased significantly, and bleeding ceased completely after butyrate provision.
2990:, chronic IFN-γ signaling is often associated with chronic inflammation. It has been shown that butyrate inhibits activity of HDAC1 that is bound to the Fas gene promoter in T cells, resulting in hyperacetylation of the Fas promoter and up-regulation of
3110:) that feed on, or ferment prebiotics, which are plant products that contain dietary fiber. These short-chain fatty acids benefit the colonocytes by increasing energy production, and may protect against colon cancer by inhibiting cell proliferation.
5011:
medium-chain fatty acids such as hexanoate, octanoate, and decanoate, but not propionate or butyrate, indicating that valproic acid is taken up into the brain via a transport system for medium-chain fatty acids, not short-chain fatty acids.
4700:
2259:) baits use butyric acid as their ester base. It is not clear whether fish are attracted by the butyric acid itself or the substances added to it. Butyric acid was one of the few organic acids shown to be palatable for both
5778:
Cholan, Pradeep
Manuneedhi; Han, Alvin; Woodie, Brad R.; Watchon, Maxinne; Kurz, Angela RM; Laird, Angela S.; Britton, Warwick J.; Ye, Lihua; Holmes, Zachary C.; McCann, Jessica R.; David, Lawrence A. (9 November 2020).
1013:
985:
1376:. By 1818, he had purified it sufficiently to characterize it. However, Chevreul did not publish his early research on butyric acid; instead, he deposited his findings in manuscript form with the secretary of the
1097:
8011:
1675:
One pathway for butyrate biosynthesis. Relevant enzymes: acetoacetyl-CoA thiolase, NAD- and NADP-dependent 3-hydroxybutyryl-CoA dehydrogenase, 3-hydroxybutyryl-CoA dehydratase, and NAD-dependent butyryl-CoA
5959:
Yonezawa H, Osaki T, Hanawa T, Kurata S, Zaman C, Woo TD, Takahashi M, Matsubara S, Kawakami H, Ochiai K, Kamiya S (2012). "Destructive effects of butyrate on the cell envelope of
Helicobacter pylori".
6626:
Belcheva, Antoaneta; Irrazabal, Thergiory; Robertson, Susan J.; Streutker, Catherine; Maughan, Heather; Rubino, Stephen; Moriyama, Eduardo H.; Copeland, Julia K.; Kumar, Sachin (17 July 2014).
5525:
Di Bella, Stefano; Sanson, Gianfranco; Monticelli, Jacopo; Zerbato, Verena; Principe, Luigi; Giuffrè, Mauro; Pipitone, Giuseppe; Luzzati, Roberto (29 February 2024). Staley, Christopher (ed.).
4114:
Seedorf, H.; Fricke, W. F.; Veith, B.; Bruggemann, H.; Liesegang, H.; Strittmatter, A.; Miethke, M.; Buckel, W.; Hinderberger, J.; Li, F.; Hagemeier, C.; Thauer, R. K.; Gottschalk, G. (2008).
2839:
Butyrate exerts a key role for the maintenance of immune homeostasis both locally (in the gut) and systemically (via circulating butyrate). It has been shown to promote the differentiation of
3171:. Butyric acid and other HDAC inhibitors have been used in preclinical research to assess the transcriptional, neural, and behavioral effects of HDAC inhibition in animals addicted to drugs.
2634:
and the liver for the generation of ATP during energy metabolism; however, some butyrate is absorbed in the distal colon, which is not connected to the portal vein, thereby allowing for the
1051:
7739:
1804:
is produced in the last step of the fermentation. Three molecules of ATP are produced for each glucose molecule, a relatively high yield. The balanced equation for this fermentation is
3024:
Butyrate has been shown to be a critical mediator of the colonic inflammatory response. It is responsible for about 70% of energy from the colonocytes, being a critical SCFA in colon
8505:
8004:
2920:
ligand. It has been shown to be a critical mediator of the colonic inflammatory response. It possesses both preventive and therapeutic potential to counteract inflammation-mediated
5613:
Furusawa, Yukihiro; Obata, Yuuki; Fukuda, Shinji; et al. (13 November 2013). "Commensal microbe-derived butyrate induces the differentiation of colonic regulatory T cells".
2085:
Fructans are another source of prebiotic soluble dietary fibers which can be digested to produce butyrate. They are often found in the soluble fibers of foods which are high in
6474:
Encarnação, J. C.; Abrantes, A. M.; Pires, A. S.; et al. (30 July 2015). "Revisit dietary fiber on colorectal cancer: butyrate and its role on prevention and treatment".
3125:
Owing to the importance of butyrate as an inflammatory regulator and immune system contributor, butyrate depletions could be a key factor influencing the pathogenesis of many
7997:
3682:
2020:
drops below 5, they switch into butanol and acetone production to prevent further lowering of the pH. Two molecules of butanol are formed for each molecule of acetone.
2833:
4647:
1082:
3959:"International Union of Basic and Clinical Pharmacology. LXXXII: Nomenclature and Classification of Hydroxy-carboxylic Acid Receptors (GPR81, GPR109A, and GPR109B)"
2820:
A depletion of butyrate in the gut is typically caused by an absence or depletion of butyrate-producing-bacteria (BPB). This depletion in BPB leads to microbial
3113:
Conversely, some researchers have sought to eliminate butyrate and consider it a potential cancer driver. Studies in mice indicate it drives transformation of
1364:. The acid does not occur widely in nature, but its esters are widespread. It is a common industrial chemical and an important component in the mammalian gut.
7732:
503:
8494:
8168:
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3048:
in cancer cells, which leads to butyrate not being properly metabolized. This phenomenon leads to the accumulation of butyrate in the nucleus, acting as a
2034:
For commercial purposes
Clostridium species are used preferably for butyric acid or butanol production. The most common species used for probiotics is the
3004:
agonists studied, butyrate also produces marked anti-inflammatory effects in a variety of tissues, including the brain, gastrointestinal tract, skin, and
3072:, resulting in hyperacetylation of the Fas promoter and upregulation of Fas receptor on the T cell surface. It is thus suggested that butyrate enhances
6566:
Prasanna Kumar, S.; Thippeswamy, G.; Sheela, M.L.; et al. (October 2008). "Butyrate-induced phosphatase regulates VEGF and angiogenesis via Sp1".
5209:
2244:, have mostly pleasant aromas or tastes. As a consequence, they are used as food and perfume additives. It is an approved food flavoring in the EU
8557:
7725:
1104:
3445:
954:
6990:
5527:"Clostridioides difficile infection: history, epidemiology, risk factors, prevention, clinical manifestations, treatment, and future options"
4533:
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3579:
3562:
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2583:
1882:
927:
2638:
of butyrate to multiple organ systems through the circulatory system. Butyrate that has reached systemic circulation can readily cross the
3386:
3726: : 73–79; in a footnote spanning pages 75–76, he mentions that he had found a substance that is responsible for the smell of butter.
8311:
5152:
Donohoe, Dallas R.; Garge, Nikhil; Zhang, Xinxin; Sun, Wei; O'Connell, Thomas M.; Bunger, Maureen K.; Bultman, Scott J. (4 May 2011).
3699:
3085:
1775:
42:
8487:
4914:"Pharmacokinetics of rectal drug administration, Part I. General considerations and clinical applications of centrally acting drugs"
2887:
2856:
2803:
2587:
2541:
2496:
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1512:
468:
1386:
58:
8547:
6601:
3828:"Short Chain Fatty Acids in the Colon and Peripheral Tissues: A Focus on Butyrate, Colon Cancer, Obesity and Insulin Resistance"
2674:(ACSM1, ACSM2B, ASCM3, ACSM4, ACSM5, and ACSM6), also known as butyrate–CoA ligase. The metabolite produced by this reaction is
2630:
Butyrate that is produced in the colon through microbial fermentation of dietary fiber is primarily absorbed and metabolized by
2251:
Due to its powerful odor, it has also been used as a fishing bait additive. Many of the commercially available flavors used in
6415:
Vanhoutvin SA, Troost FJ, Hamer HM, Lindsey PJ, Koek GH, Jonkers DM, Kodde A, Venema K, Brummer RJ (2009). Bereswill S (ed.).
3159:
that can cause histone deacetylation and repression of gene expression. HDACs are important regulators of synaptic formation,
7374:
4671:
622:
303:
7368:
6177:
Graff EC, Fang H, Wanders D, Judd RL (February 2016). "Anti-inflammatory effects of the hydroxycarboxylic acid receptor 2".
5947:
5943:
4644:
32:
7748:
3780:"Stepwise Discriminant Analysis of Free Fatty Acid Profiles for Identifying Sources of Lipolytic Enzymes in Rancid Butter"
3300:
1869:
1047:
6519:"Butyrate suppresses colonic inflammation through HDAC1-dependent Fas upregulation and Fas-mediated apoptosis of T cells"
6093:
Offermanns S, Schwaninger M (2015). "Nutritional or pharmacological activation of HCA(2) ameliorates neuroinflammation".
6046:"Butyrate suppresses colonic inflammation through HDAC1-dependent Fas upregulation and Fas-mediated apoptosis of T cells"
5280:"Reduced genetic potential for butyrate fermentation in the gut microbiome of infants who develop allergic sensitization"
3076:
of T cells in the colonic tissue and thereby eliminates the source of inflammation (IFN-γ production). Butyrate inhibits
3052:(HDAC) inhibitor. One mechanism underlying butyrate function in suppression of colonic inflammation is inhibition of the
1241:
8480:
8043:
7979:
4339:"Bifidobacteria and Butyrate-Producing Colon Bacteria: Importance and Strategies for Their Stimulation in the Human Gut"
3130:
2009:
1724:
1377:
1041:
399:
7314:
7989:
5838:"Diet is a major factor governing the fecal butyrate-producing community structure across Mammalia, Aves and Reptilia"
3268:
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2635:
2023:
The change in the pathway occurs after acetoacetyl CoA formation. This intermediate then takes two possible pathways:
1461:
431:
7439:
2870:
The odor of butyric acid, which emanates from the sebaceous follicles of all mammals, works on the tick as a signal.
6044:
Zimmerman MA, Singh N, Martin PM, Thangaraju M, Ganapathy V, Waller JL, Shi H, Robertson KD, Munn DH, Liu K (2012).
4593:
1090:
7510:
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7308:
7302:
5100:
4028:
Carroll, Mark J.; Berenbaum, May R. (2002). "Behavioral responses of the parsnip webworm to host plant volatiles".
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1987:
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8375:
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2233:(CAB), which is used in a wide variety of tools, paints, and coatings, and is more resistant to degradation than
1925:
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proliferation. Conversely, a high-fiber diet results in higher butyric acid concentration and inhibition of
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Adenosine triphosphate + butyric acid + coenzyme A → adenosine monophosphate + pyrophosphate + butyryl-CoA
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4391:. Department of Gastroenterology Translational Nutrition Science, Monash University, Victoria, Australia
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6921:"Mécanismes épigénétiques et troubles de l'usage d'alcool : une cible thérapeutique intéressante?"
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such as butyrate from fermentable fibers may contribute to the role of dietary fiber in colon cancer.
8542:
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7954:
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4972:"Small molecular drug transfer across the blood–brain barrier via carrier-mediated transport systems"
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5723:"Regulation of the effector function of CD8+ T cells by gut microbiota-derived metabolite butyrate"
5378:
Kumar J, Rani K, Datt C (2020). "Molecular link between dietary fibre, gut microbiota and health".
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3567:
3469:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
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3049:
3028:. Butyrate possesses both preventive and therapeutic potential to counteract inflammation-mediated
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2598:
2126:
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107:
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5405:
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4178:
4053:
3882:"Formation of short chain fatty acids by the gut microbiota and their impact on human metabolism"
3415:; most of the butyrate that enters the circulatory system by this route is taken up by the liver.
3029:
2921:
2747:
2537:
1684:
1508:
7924:
6214:"The homeostatic role of neuropeptide Y in immune function and its impact on mood and behaviour"
4865:"Butyrate, neuroepigenetics and the gut microbiome: Can a high fiber diet improve brain health?"
4412:"Evidence-based dietary management of functional gastrointestinal symptoms: The FODMAP approach"
2074:. One study found that resistant starch consistently produces more butyrate than other types of
8148:
4083:
3662:
3613:, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 27 October 2020)
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6376:"Oncogenic Ras promotes butyrate-induced apoptosis through inhibition of gelsolin expression"
5154:"The Microbiome and Butyrate Regulate Energy Metabolism and Autophagy in the Mammalian Colon"
4179:"Butyric acid production by Clostridium butyricum with integrated extraction and pertraction"
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3715:
1982:
in an alternative pathway, which starts as butyrate fermentation. Some of these species are:
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5666:"Metabolites produced by commensal bacteria promote peripheral regulatory T-cell generation"
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6923:[Epigenetic mechanisms and alcohol use disorders: a potential therapeutic target].
4733:"Dietary gut microbial metabolites, short-chain fatty acids, and host metabolic regulation"
2774:
effects) in humans. These effects occur through its metabolism by mitochondria to generate
2675:
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5235:
Tilg H, Moschen AR (September 2014). "Microbiota and diabetes: an evolving relationship".
5112:
4797:"The environment of regulatory T cell biology: cytokines, metabolites, and the microbiome"
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Butyrate has established antimicrobial properties in humans that are mediated through the
2763:
2703:
2650:). Other transporters that mediate the passage of butyrate across lipid membranes include
2241:
2229:
Butyric acid is used in the preparation of various butyrate esters. It is used to produce
2130:
2086:
1963:
1465:
1449:
1422:
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1341:
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6628:"Gut microbial metabolism drives transformation of MSH2-deficient colon epithelial cells"
6602:"Low-carb diet cuts risk of colon cancer, study finds | University of Toronto Media Room"
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5574:"Microbiome-driven allergic lung inflammation is ameliorated by short chain fatty acids"
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is the material that is mainly relevant in biological systems. It is one of two primary
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Butyrate's effects on the immune system are mediated through the inhibition of class I
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Rivière, Audrey; Selak, Marija; Lantin, David; Leroy, Frédéric; De Vuyst, Luc (2016).
4213:"Microbial degradation products influence colon cancer risk: the butyrate controversy"
4194:
4076:
8521:
8430:
8410:
8362:
8301:
8291:
8113:
7674:
7655:
7624:
7559:
7492:
7470:
7181:
7169:
7103:
7097:
7085:
7049:
7043:
7011:
6778:
6693:
6676:
6360:
6314:"Effects of Intestinal Microbial–Elaborated Butyrate on Oncogenic Signaling Pathways"
5409:
4929:
4631:
4428:
4411:
3658:
3441:
3436:
3262:
3167:
formation. Class I HDACs are known to be involved in mediating the development of an
2825:
2767:
2691:
2610:
2597:(specifically, HDAC1, HDAC2, HDAC3, and HDAC8), a drug that inhibits the function of
2214:
2186:
2075:
1691:
1580:
1551:
1497:
1222:
884:
666:
611:
601:
254:
6905:
6517:
Zimmerman, Mary A.; Singh, Nagendra; Martin, Pamela M.; et al. (15 June 2012).
6503:
5526:
5264:
4453:
4057:
3957:
Offermanns S, Colletti SL, Lovenberg TW, Semple G, Wise A, IJzerman AP (June 2011).
3129:
conditions. It is thus essential to maintain healthy levels of butyrate in the gut.
2070:(SCFA) including butyrate, producing more SCFA than less fermentable fibers such as
8395:
8093:
7939:
7934:
7919:
7864:
7859:
7849:
7602:
7565:
7421:
7199:
7157:
7133:
7109:
7037:
7031:
5836:
Vital, Marius; Gao, Jiarong; Rizzo, Mike; Harrison, Tara; Tiedje, James M. (2015).
5664:
Arpaia, Nicholas; Campbell, Clarissa; Fan, Xiying; et al. (13 November 2013).
5650:
4001:
Offermanns S, Colletti SL, IJzerman AP, Lovenberg TW, Semple G, Wise A, Waters MG.
3739:(Extract of a letter from Mr. Chevreul to the editors of the Journal of Pharmacy),
3408:
3077:
3065:
3041:
3005:
2991:
2759:
2158:
2082:
animals such as cattle is responsible for the butyrate content of milk and butter.
2016:
These bacteria begin with butyrate fermentation, as described above, but, when the
1890:
1406:
796:
372:
92:
8184:
8073:
6190:
5796:
3952:
3950:
3897:
3737:"Extrait d'une lettre de M. Chevreul à MM. les Rédacteurs du Journal de Pharmacie"
7717:
6441:
6106:
5441:
5424:
5043:
4880:
4485:
4468:
4177:
Zigová, Jana; Šturdı́k, Ernest; Vandák, Dušan; Schlosser, Štefan (October 1999).
2702:. In particular, it is an important energy source for cells lining the mammalian
8459:
8451:
8229:
7884:
7879:
7874:
7854:
7844:
7769:
7618:
7205:
7073:
7061:
5995:
McGee DJ, George AE, Trainor EA, Horton KE, Hildebrandt E, Testerman TL (2011).
5423:
Consolandi, Clarissa; Turroni, Silvia; Emmi, Giacomo; et al. (April 2015).
4525:
4467:
Gibson, Peter R.; Varney, Jane; Malakar, Sreepurna; Muir, Jane G. (1 May 2015).
3480:
3412:
3305:
3257:
3025:
3013:
2828:, which can induce inflammation and have other adverse affects insofar as these
2631:
2252:
1903:
1441:
1372:
Butyric acid was first observed in an impure form in 1814 by the French chemist
1164:
1116:
827:
364:
6830:
6644:
6627:
6313:
5746:
5393:
5296:
5279:
5248:
5169:
8420:
8415:
8384:
8370:
8352:
8234:
8143:
8103:
8078:
8028:
7964:
7959:
7889:
7829:
7819:
7789:
7596:
7003:
6879:
6677:"Effect of butyrate enemas on the colonic mucosa in distal ulcerative colitis"
6579:
6487:
6263:"Mechanisms linking dietary fiber, gut microbiota and colon cancer prevention"
6145:
5997:"Cholesterol enhances Helicobacter pylori resistance to antibiotics and LL-37"
5721:
Luu, Maik; Weigand, Katharina; Wedi, Fatana; et al. (26 September 2018).
5492:
5345:
5321:"The human gut microbiome in early-onset type 1 diabetes from the TEDDY study"
5021:
5019:
4041:
3539:
3288:
3126:
3107:
2714:
2525:
2268:
2264:
2237:. CAB can degrade with exposure to heat and moisture, releasing butyric acid.
2202:
1751:
1426:
1414:
1390:, meaning "butter", the substance in which it was first found. The Latin name
656:
558:
292:
204:
6862:
Ajonijebu DC, Abboussi O, Russell VA, Mabandla MV, Daniels WM (August 2017).
6653:
6534:
6061:
5804:
5550:
5177:
4937:
4813:
4494:
4437:
4355:
4270:
4253:
3691:
8357:
8219:
8158:
7944:
7894:
7799:
7636:
4912:
van
Hoogdalem, Edward; de Boer, Albertus G.; Breimer, Douwe D. (July 1991).
4726:
4724:
4722:
4144:
3571:
3168:
3134:
3103:
3073:
3037:
2821:
2707:
2671:
2606:
2230:
2154:
2146:
2134:
2071:
2063:
1976:
1933:
1895:
1846:
1767:
1632:
It can be separated from aqueous solutions by saturation with salts such as
1501:
1453:
1218:
790:
420:
6946:
6937:
6920:
6897:
6848:
6796:
6751:
6661:
6587:
6552:
6495:
6460:
6401:
6392:
6375:
6352:
6298:
6247:
6198:
6163:
6114:
6079:
6030:
5981:
5973:
5937:
5879:
5861:
5822:
5764:
5707:
5642:
5599:
5558:
5511:
5460:
5401:
5364:
5305:
5256:
5195:
5082:
5061:
5005:
4987:
4913:
4898:
4839:
Figure 1: Microbial-derived molecules promote colonic Treg differentiation.
4832:
4768:
4502:
4445:
4374:
4279:
4238:
4229:
4212:
4163:
4049:
3984:
3915:
3863:
2986:. While transient IFN-γ signaling is generally associated with normal host
1671:
1413:. When butter goes rancid, butyric acid is liberated from the glyceride by
6702:
6374:
Klampfer L, Huang J, Sasazuki T, Shirasawa S, Augenlicht L (August 2004).
6279:
5781:"Conserved anti-inflammatory effects and sensing of butyrate in zebrafish"
4945:
4320:
3975:
3958:
3060:
signalling pathways. It has been shown that butyrate inhibits activity of
8138:
8118:
8108:
7809:
7784:
6012:
5542:
4590:
3198:
3053:
2975:
2971:
2909:
2751:
2162:
2138:
2079:
2051:
1958:
1790:
1763:
1759:
1687:
1584:
1103:
1096:
1089:
1062:
233:
5948:
Table 4: Some known factors that induce antimicrobial peptide expression
5689:
5634:
2907:, butyrate is the most potent promoter of intestinal regulatory T cells
1991:, the most prominent acetone and butanol producer, used also in industry
243:
8209:
8098:
6333:
6229:
5944:
Table 3: Select human antimicrobial peptides and their proposed targets
5590:
5573:
5451:
3310:
3069:
2755:
2659:
2655:
2602:
2276:
2170:
2142:
2098:
1972:
1755:
1695:
1572:
1543:
1434:
662:
589:
350:
274:
6968:
6919:
Legastelois R, Jeanblanc J, Vilpoux C, Bourguet E, Naassila M (2017).
5918:
4749:
3844:
3718:(Letter from Mr. Chevreul to the editors of the Annals of Chemistry),
8248:
8133:
8083:
6523:
American
Journal of Physiology. Gastrointestinal and Liver Physiology
4790:
4788:
4786:
4784:
4782:
3205:
3192:
2651:
2190:
2174:
2122:
2114:
2090:
2055:
1576:
1477:
1445:
1410:
1345:
867:
183:
6733:
5028:"Role of monocarboxylate transporters in drug delivery to the brain"
2586:; however, among the group of SCFAs, only butyrate is an agonist of
1680:
Butyrate is produced by several fermentation processes performed by
1234:
Except where otherwise noted, data are given for materials in their
8169:
4731:
Kasubuchi M, Hasegawa S, Hiramatsu T, Ichimura A, Kimura I (2015).
3155:
inhibitor that is selective for class I HDACs in humans. HDACs are
324:
6999:
6417:"Butyrate-induced transcriptional changes in human colonic mucosa"
5425:"Behçet's syndrome patients exhibit specific microbiome signature"
3716:"Lettre de M. Chevreul à MM. les rédacteurs des Annales de chimie"
3435:
This article incorporates text from a publication now in the
3223:
3061:
3057:
2979:
2974:. Butyrate also suppresses colonic inflammation by inhibiting the
2947:
2935:
2900:
2896:
2799:
2795:
2579:
2575:
2533:
2483:
2470:
2457:
2414:
2402:
2389:
2376:
2363:
2350:
2338:
2326:
2314:
2260:
2206:
2118:
2106:
2102:
1670:
1539:
1489:
1469:
1457:
1353:
1307:
383:
162:
150:
139:
487:
Butyric acid: InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
8204:
3680:
Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic".
3114:
2939:
2451:
2296:
2150:
2059:
1473:
1437:
579:
314:
7993:
7721:
6972:
5476:"A metagenomic study of the gut microbiome in Behcet's disease"
5319:
Vatanen, T.; Franzosa, E.A.; Schwager, R.; et al. (2018).
3214:
of butyric acid. It is the form found in biological systems at
1425:
that reacts with bases and affects many metals. It is found in
6864:"Epigenetics: a link between addiction and social environment"
5895:
5893:
5891:
5889:
3751:(This principle , which I have since named "butyric acid", … )
3187:
2614:
2201:
Butyric acid reacts as a typical carboxylic acid: it can form
2110:
1481:
6675:
Scheppach, W.; Sommer, H.; Kirchner, T.; et al. (1992).
5474:
Ye, Zi; Zhang, Ni; Wu, Chunyan; et al. (4 August 2018).
3996:
3994:
3606:
in
Linstrom, Peter J.; Mallard, William G. (eds.);
2221:, is commonly used as the intermediate to obtain the others.
1271:
6813:
Walker DM, Cates HM, Heller EA, Nestler EJ (February 2015).
4610:
Kasumyan A, Døving K (2003). "Taste preferences in fishes".
436:
41:
31:
4516:
Jenkins, P. R. (1985). "Carboxylic acids and derivatives".
2017:
860:α = 90°, β = 111.45°, γ = 90°
3608:
2717:, which is naturally present in butter, is metabolized by
1302:, meaning "butter"), also known under the systematic name
3813:. Inchem.org (23 November 1998). Retrieved on 2020-10-27.
3762:
Recherches chimiques sur les corps gras d'origine animale
3102:, which include butyric acid, are produced by beneficial
2582:, which function as nutrient sensors that facilitate the
1283:
1277:
1268:
1121:
71 to 72 °C (160 to 162 °F; 344 to 345 K)
1074:
8312:
6718:"Transcriptional and epigenetic mechanisms of addiction"
4678:. International Union of Basic and Clinical Pharmacology
4410:
Gibson, Peter R.; Shepherd, Susan J. (1 February 2010).
4389:"Frequently asked questions in the area of diet and IBS"
4252:
Cummings JH, Macfarlane GT, Englyst HN (February 2001).
4009:. International Union of Basic and Clinical Pharmacology
3749:"Ce principe, que j'ai appelé depuis acid butérique, … "
2982:
signaling pathways, which is mediated partially through
2966:; through these actions, it increases the expression of
4863:
Bourassa MW, Alim I, Bultman SJ, Ratan RR (June 2016).
2942:
inhibition on histone H3. In vitro, butyrate increases
2605:
in cells. Histone acetylation loosens the structure of
2030:
acetoacetyl CoA → butyryl CoA → butyraldehyde → butanol
6312:
Chen, Jiezhong; Zhao, Kong-Nan; Vitetta, Luis (2019).
4795:
Hoeppli RE, Wu D, Cook L, Levings MK (February 2015).
2706:(colonocytes). Without butyrates, colon cells undergo
2046:
Highly-fermentable fiber residues, such as those from
3411:
from the colon enters the circulatory system via the
2240:
Low-molecular-weight esters of butyric acid, such as
1286:
1280:
1274:
1265:
8450:
8443:
8310:
8256:
8247:
8174:
Tooltip
Vesicular inhibitory amino acid transporter
8167:
8051:
8042:
7684:
7665:
7646:
7587:
7544:
7449:
7384:
7251:
7010:
6808:
6806:
4120:, a Strict Anaerobe with Unique Metabolic Features"
1262:
302:
6815:"Regulation of chromatin states by drugs of abuse"
4075:
6261:Zeng, Huawei; Lazarova, DL; Bordonaro, M (2014).
4645:Japanese Whalers Injured by Acid-Firing Activists
3467:"Applications to Specific Classes of Compounds".
3016:of colonic mucosa and the enteric immune system.
2601:enzymes, thereby favoring an acetylated state of
3747: : 79–81. On p. 81, he named butyric acid:
3741:Journal de Pharmacie et des sciences accessoires
371:
363:
8258:
5278:Cait, Alissa; Cardenas, Erick (December 2019).
4572:. Vol. 24, no. 1. Conservation OnLine
4295:"Effect of feed on the composition of milk fat"
4124:Proceedings of the National Academy of Sciences
1078:
616:163.75 °C (326.75 °F; 436.90 K)
477:InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
125:
117:
6964:NIST Standard Reference Data for butanoic acid
4469:"Food components and irritable bowel syndrome"
3683:Ullmann's Encyclopedia of Industrial Chemistry
3121:Potential treatments from butyrate restoration
2775:
1801:
1800:) are formed as waste products. Subsequently,
1690:. This fermentation pathway was discovered by
1507:In humans, butyric acid is one of two primary
1492:can detect it only in concentrations above 10
1417:. It is one of the fatty acid subgroup called
8005:
7733:
6984:
4332:
4330:
2670:Butyric acid is metabolized by various human
1663:, is less soluble in hot water than in cold.
1480:with good scent detection abilities, such as
8:
6128:Chai JT, Digby JE, Choudhury RP (May 2013).
5572:Cait, Alissa; Hughes, Michael R (May 2018).
4695:
4693:
4551:Industrial Plastics: Theory and Applications
4074:; Evert, Ray F.; Eichhorn, Susan E. (2005).
3611:, NIST Standard Reference Database Number 69
3454:(11th ed.). Cambridge University Press.
2913:and the only one among the group that is an
1849:reduction and crotonate disproportionation.
1766:, as happens in most organisms. Pyruvate is
8021:
6050:Am. J. Physiol. Gastrointest. Liver Physiol
5902:"Human antimicrobial peptides and proteins"
3875:
3873:
3821:
3819:
3623:
3621:
3619:
3407:Most of the butyrate that is absorbed into
3148:
8447:
8253:
8048:
8012:
7998:
7990:
7740:
7726:
7718:
6991:
6977:
6969:
6267:World Journal of Gastrointestinal Oncology
5284:Journal of Allergy and Clinical Immunology
5127:"Butanoate metabolism – Reference pathway"
4416:Journal of Gastroenterology and Hepatology
4258:The American Journal of Clinical Nutrition
2962:(Tregs) through the inhibition of class I
2955:
1336:. It is an oily, colorless liquid with an
606:−5.1 °C (22.8 °F; 268.0 K)
584:Unpleasant, similar to vomit or body odor
452:
264:
221:
213:
20:
8506:Glutamate metabolism/transport modulators
7765:β-Hydroxybutyric acid (β-hydroxybutyrate)
6936:
6887:
6838:
6786:
6767:"Epigenetic mechanisms of drug addiction"
6741:
6692:
6643:
6542:
6450:
6440:
6391:
6342:
6332:
6288:
6278:
6237:
6153:
6069:
6020:
5927:
5917:
5869:
5812:
5754:
5697:
5589:
5501:
5491:
5450:
5440:
5354:
5344:
5295:
5185:
5051:
4995:
4888:
4822:
4812:
4758:
4748:
4666:
4664:
4662:
4660:
4484:
4427:
4364:
4354:
4310:
4269:
4228:
4206:
4204:
4153:
4143:
3974:
3905:
3853:
3843:
3795:
3675:
3673:
3671:
1567:In industry, butyric acid is produced by
408:
8406:Valproate semisodium (divalproex sodium)
8317:Tooltip γ-Aminobutyrate aminotransferase
8053:
6716:Robison AJ, Nestler EJ (November 2011).
5133:. Kanehisa Laboratories. 1 November 2017
3826:McNabney, S. M.; Henagan, T. M. (2017).
3218:. A butyric (or butanoic) compound is a
3201:
3195:
3000:
2916:
2890:
2859:
2806:
2732:
2547:
2499:
2286:
2078:. The production of SCFA from fibers in
2027:acetoacetyl CoA → acetoacetate → acetone
1917:
1913:
1909:
1851:
1838:
1834:
1830:
1826:
1822:
1818:
1814:
1810:
1796:
1785:
1694:in 1861. Examples of butyrate-producing
1658:
1651:
1647:
1643:
1639:
1613:
1609:
1605:
1601:
1597:
1593:
1518:
1331:
1327:
1323:
1319:
6568:Archives of Biochemistry and Biophysics
6212:Farzi A, Reichmann F, Holzer P (2015).
5210:"triacylglycerol lipase – Homo sapiens"
5131:Kyoto Encyclopedia of Genes and Genomes
5077:
5075:
3654:
3652:
3650:
3648:
3646:
3459:
3400:
2571:(SCFAs), butyrate is an agonist at the
1472:somewhat like butter and an unpleasant
508:
473:
448:
340:
242:
5108:
5098:
4566:"Care of Plastics: Malignant plastics"
4254:"Prebiotic digestion and fermentation"
3764:(Paris, France: F.G. Levrault, 1823),
3599:
3597:
3595:
3593:
3591:
3506:
3504:
3502:
3500:
2542:hydroxycarboxylic acid receptor 2
1513:hydroxycarboxylic acid receptor 2
1135:440 °C (824 °F; 713 K)
255:
5216:. Technische Universität Braunschweig
4082:. W. H. Freemanand Company. pp.
3880:Morrison, D. J.; Preston, T. (2016).
3563:CRC Handbook of Chemistry and Physics
3555:
3553:
3551:
3549:
2584:homeostatic control of energy balance
2105:(although some wheat strains such as
1876:Acetoacetyl coenzyme A converts into
480:Key: FERIUCNNQQJTOY-UHFFFAOYSA-N
192:
171:
7:
6868:Cellular and Molecular Life Sciences
3012:release and promotes the functional
3008:. Butyrate binding at FFAR3 induces
8094:Deramciclane (EGIS-3886, EGYT-3886)
6380:The Journal of Biological Chemistry
6130:"GPR109A and vascular inflammation"
5537:(2). Mayuresh Abhyankar: e0013523.
4701:"Butanoic acid and Sodium butyrate"
3513:"Crystal structure of butyric acid"
2725:and butyrate through the reaction:
2267:. The substance has been used as a
1889:β-hydroxybutyryl CoA converts into
1845:Other pathways to butyrate include
490:Key: FERIUCNNQQJTOY-UHFFFAOYAP
353:
323:
7375:6,9,12,15,18,21-Tetracosahexaenoic
4003:"Hydroxycarboxylic acid receptors"
3511:Strieter FJ, Templeton DH (1962).
3086:vascular endothelial growth factor
2713:In humans, the butyrate precursor
2181:, such as fructooligosaccharides (
1883:β-hydroxybutyryl-CoA dehydrogenase
1776:pyruvate:ferredoxin oxidoreductase
36:Skeletal structure of butyric acid
14:
7369:9,12,15,18,21-Tetracosapentaenoic
4553:(6th ed.). Cengage Learning.
4312:10.3168/jds.S0022-0302(91)78510-X
3797:10.3168/jds.S0022-0302(83)82052-9
3778:Woo, A.H.; Lindsay, R.C. (1983).
2874:Immunomodulation and inflammation
2746:Butyrate has numerous effects on
2617:. In general, it is thought that
2303:
2273:Sea Shepherd Conservation Society
6779:10.1016/j.neuropharm.2013.04.004
4930:10.2165/00003088-199121010-00002
4676:IUPHAR/BPS Guide to Pharmacology
4632:10.1046/j.1467-2979.2003.00121.x
4520:. Vol. 7. pp. 96–160.
4429:10.1111/j.1440-1746.2009.06149.x
4007:IUPHAR/BPS Guide to Pharmacology
3428:
2710:(i.e., self-digestion) and die.
2613:attraction between histones and
1863:Acetyl coenzyme A converts into
1409:of butyric acid compose 3–4% of
1258:
1003:
57:
8263:Tooltip Glutamate decarboxylase
7775:Acetoacetic acid (acetoacetate)
3665:. Retrieved on 27 October 2020.
1538:Butyric acid is present as its
1344:(2-methylpropanoic acid) is an
1238:(at 25 °C , 100 kPa).
8558:Histone deacetylase inhibitors
7749:Histone deacetylase inhibitors
4654:, newser.com, 10 February 2010
3473:The Royal Society of Chemistry
3387:β-Hydroxy β-methylbutyric acid
3094:In summary, the production of
2984:histone deacetylase inhibition
2782:or through one or more of its
2678:, and is produced as follows:
2646:(i.e., certain members of the
2288:Human enzyme and GPCR binding
1460:and as a product of anaerobic
46:Flat structure of butyric acid
1:
8481:Receptor/signaling modulators
7980:Receptor/signaling modulators
6476:Cancer and Metastasis Reviews
6191:10.1016/j.metabol.2015.10.001
5797:10.1080/19490976.2020.1824563
5531:Clinical Microbiology Reviews
4518:General and Synthetic Methods
4293:Grummer RR (September 1991).
4195:10.1016/S0032-9592(99)00007-2
3898:10.1080/19490976.2015.1134082
3631:. Chemister.ru. 19 March 2007
3301:List of saturated fatty acids
2690:, butyrate is metabolized by
1870:acetyl-CoA-acetyl transferase
1356:of butyric acid are known as
8499:receptor positive modulators
6694:10.1016/0016-5085(92)91094-K
6442:10.1371/journal.pone.0006759
6107:10.1016/j.molmed.2015.02.002
6001:Antimicrob. Agents Chemother
5442:10.1016/j.autrev.2014.11.009
5044:10.2174/13816128113199990462
4881:10.1016/j.neulet.2016.02.009
4486:10.1053/j.gastro.2015.02.005
3560:Lide, David R., ed. (2009).
3131:Fecal microbiota transplants
3084:activity and downregulating
2788:class I histone deacetylases
2648:SLC16A group of transporters
2644:monocarboxylate transporters
2551:, also known as GPR109A), a
2010:Clostridium aurantibutyricum
1750:The pathway starts with the
1725:Faecalibacterium prausnitzii
1421:. Butyric acid is a typical
511:Butyric acid: O=C(O)CCC
391:Butyric acid: ES5425000
283:Butyric acid: 203-532-3
8026:Tooltip γ-Aminobutyric acid
7905:Sodium oxybate (GHB sodium)
6765:Nestler EJ (January 2014).
5026:Vijay N, Morris ME (2014).
4526:10.1039/9781847556196-00096
4211:Lupton JR (February 2004).
4030:Journal of Chemical Ecology
3481:10.1039/9781849733069-00648
3269:Estradiol benzoate butyrate
3153:Tooltip histone deacetylase
1936:group replaces CoA to form
1902:Crotonyl CoA converts into
1153:or concentration (LD, LC):
27:
8574:
6831:10.1016/j.conb.2014.11.002
6645:10.1016/j.cell.2014.04.051
5747:10.1038/s41598-018-32860-x
5394:10.1007/s11033-020-05611-3
5297:10.1016/j.jaci.2019.06.029
5249:10.1136/gutjnl-2014-306928
5170:10.1016/j.cmet.2011.02.018
3263:Cellulose acetate butyrate
2884:G-protein coupled receptor
2792:G-protein coupled receptor
2562:G protein-coupled receptor
2231:cellulose acetate butyrate
1988:Clostridium acetobutylicum
1949:The phosphate group joins
1533:G protein-coupled receptor
1385:
1299:
8472:
8328:3-Hydrazinopropionic acid
7973:
7945:Valproic acid (valproate)
7755:
6880:10.1007/s00018-017-2493-1
6580:10.1016/j.abb.2008.07.004
6488:10.1007/s10555-015-9578-9
6146:10.1007/s11883-013-0325-9
5493:10.1186/s40168-018-0520-6
5381:Molecular Biology Reports
5346:10.1038/s41586-018-0620-2
4918:Clinical Pharmacokinetics
4549:Lokensgard, Erik (2015).
4343:Frontiers in Microbiology
3540:10.1107/S0365110X6200328X
3175:Butyrate salts and esters
3157:histone-modifying enzymes
2766:(e.g., it has pronounced
2573:free fatty acid receptors
2217:derivatives. The latter,
2042:Fermentable fiber sources
2003:Clostridium tetanomorphum
1926:butyryl CoA dehydrogenase
1739:Butyrivibrio fibrisolvens
1550:) and in the seed of the
1232:
1188:
1149:
984:
979:
877:
805:
519:
499:
464:
100:
82:
70:
65:
56:
26:
8488:GABA receptor modulators
8274:3-Mercaptopropionic acid
8058:Tooltip GABA transporter
7428:7,10,13-Octadecatrienoic
6535:10.1152/ajpgi.00543.2011
6062:10.1152/ajpgi.00543.2011
4814:10.3389/fimmu.2015.00061
4356:10.3389/fmicb.2016.00979
4299:Journal of Dairy Science
4217:The Journal of Nutrition
3811:ICSC 1334 – Butyric acid
3784:Journal of Dairy Science
3692:10.1002/14356007.a05_235
3316:Histone-modifying enzyme
3306:Hershey's milk chocolate
3117:colon epithelial cells.
3082:Sp1 transcription factor
2845:Clostridioides difficile
2784:histone-modifying enzyme
2737:dibutyrin + butyric acid
2109:contain lower amounts),
1996:Clostridium beijerinckii
1718:Clostridium pasteurianum
1042:Precautionary statements
87:1-Propanecarboxylic acid
8548:Foul-smelling chemicals
7795:Butyric acid (butyrate)
5087:. University of Alberta
4596:25 January 2010 at the
4145:10.1073/pnas.0711093105
4042:10.1023/A:1021093114663
3963:Pharmacological Reviews
3934:The Good Scents Company
3686:. Weinheim: Wiley-VCH.
3451:Encyclopædia Britannica
3376:(succinic semialdehyde)
3100:Short-chain fatty acids
2994:on the T-cell surface.
2970:, an anti-inflammatory
2958:) and promotes colonic
2952:transcription regulator
2938:, which it induces via
2905:short-chain fatty acids
2830:short-chain fatty acids
2698:or ATP) source through
2569:short-chain fatty acids
2068:short-chain fatty acids
1789:) and two molecules of
1732:Fusobacterium nucleatum
1419:short-chain fatty acids
1171:2000 mg/kg (oral, rat)
749:Magnetic susceptibility
630:Sublimes at −35 °C
7578:7,10,13-Eicosatrienoic
7434:9,12,15-Eicosatrienoic
6393:10.1074/jbc.M405197200
5974:10.1099/jmm.0.039040-0
5862:10.1038/ismej.2014.179
4988:10.1602/neurorx.2.1.54
4707:. The Binding Database
4271:10.1093/ajcn/73.2.415s
4264:(2 Suppl): 415S–420S.
3609:NIST Chemistry WebBook
3520:Acta Crystallographica
2882:and activation of its
2750:and related diseases (
2719:triacylglycerol lipase
2696:adenosine triphosphate
2688:short-chain fatty acid
2095:cruciferous vegetables
1865:acetoacetyl coenzyme A
1677:
1667:Microbial biosynthesis
1587:to the final product.
1484:, can detect it at 10
1374:Michel Eugène Chevreul
1306:, is a straight-chain
1085:
669:. Slightly soluble in
47:
37:
7910:Sodium phenylbutyrate
7760:3,3'-Diindolylmethane
6819:Curr. Opin. Neurobiol
6280:10.4251/wjgo.v6.i2.41
3976:10.1124/pr.110.003301
3475:. 2014. p. 746.
3350:γ-Hydroxybutyric acid
3345:β-Hydroxybutyric acid
3340:α-Hydroxybutyric acid
3064:that is bound to the
2933:antimicrobial peptide
2780:fatty acid metabolism
2700:fatty acid metabolism
2636:systemic distribution
2619:transcription factors
2036:Clostridium butyricum
1971:Several species form
1704:Clostridium butyricum
1674:
1084:
853: = 6.82 Å,
849: = 8.01 Å,
45:
35:
7955:Valproate semisodium
6938:10.1051/jbio/2017014
6925:Biologie Aujourd'hui
6773:. 76 Pt B: 259–268.
6134:Curr Atheroscler Rep
6013:10.1128/AAC.00016-11
5543:10.1128/cmr.00135-23
5429:Autoimmunity Reviews
5290:(6): 1638–1647. E3.
4564:Williams, R. Scott.
4230:10.1093/jn/134.2.479
4183:Process Biochemistry
4118:Clostridium kluyveri
3382:β-Methylbutyric acid
3364:(α-ketobutyric acid)
3335:Hydroxybutyric acids
3133:(to restore BPB and
3096:volatile fatty acids
2964:histone deacetylases
2880:histone deacetylases
2815:In the mammalian gut
2694:as an energy (i.e.,
2275:to disrupt Japanese
2157:, the white part of
1878:β-hydroxybutyryl CoA
1711:Clostridium kluyveri
1636:. The calcium salt,
1067:(fire diamond)
857: = 10.14 Å
761:Thermal conductivity
596:0.9528 g/cm (25 °C)
72:Preferred IUPAC name
8195:Chicago sky blue 6B
8069:4-Aminovaleric acid
6529:(12): G1405–G1415.
6433:2009PLoSO...4.6759V
5854:2015ISMEJ...9..832V
5739:2018NatSR...814430L
5690:10.1038/nature12726
5682:2013Natur.504..451A
5635:10.1038/nature12721
5627:2013Natur.504..446F
5337:2018Natur.562..589V
4650:8 June 2010 at the
4624:2003AqFF....4..289K
4479:(6): 1158–1174.e4.
4136:2008PNAS..105.2128S
3568:Boca Raton, Florida
3532:1962AcCry..15.1240S
3326:Histone deacetylase
3161:synaptic plasticity
3146:Butyric acid is an
3050:histone deacetylase
2903:(GPR41). Among the
2786:targets (i.e., the
2640:blood–brain barrier
2599:histone deacetylase
2538:endogenous agonists
2289:
2099:Sources of fructans
2062:are transformed by
1858:Responsible enzyme
1778:. Two molecules of
1745:Eubacterium limosum
1509:endogenous agonists
1378:Academy of Sciences
646:Solubility in water
594:1.135 g/cm (−43 °C)
566: g·mol
447:Butyric acid:
407:Butyric acid:
362:Butyric acid:
322:Butyric acid:
301:Butyric acid:
241:Butyric acid:
212:Butyric acid:
191:Butyric acid:
170:Butyric acid:
149:Butyric acid:
116:Butyric acid:
23:
7631:8,11-Eicosadienoic
7511:Dihomo-γ-linolenic
7440:β-Eicosatetraenoic
7339:Dihomo-α-linolenic
7224:Heptatriacontanoic
6722:Nat. Rev. Neurosci
6334:10.3390/nu11051026
6230:10.1111/apha.12445
6218:Acta Physiol (Oxf)
5727:Scientific Reports
5591:10.1038/mi.2017.75
5578:Mucosal Immunology
4612:Fish and Fisheries
3370:(acetoacetic acid)
3030:ulcerative colitis
2960:regulatory T cells
2922:ulcerative colitis
2841:regulatory T cells
2748:energy homeostasis
2287:
1678:
1500:, it is used as a
1498:food manufacturing
1464:(including in the
1380:in Paris, France.
1242:Infobox references
1189:Related compounds
1086:
724:5.35·10 L·atm/mol
702:9.62 kPa (100 °C)
48:
38:
21:
8515:
8514:
8468:
8467:
8439:
8438:
8401:Valproate pivoxil
8365:
8338:γ-Acetylenic-GABA
8243:
8242:
7987:
7986:
7965:Vorinostat (SAHA)
7950:Valproate pivoxil
7835:Indole-3-carbinol
7815:Diallyl disulfide
7715:
7714:
7236:Nonatriacontanoic
7230:Octatriacontanoic
6874:(15): 2735–2747.
6771:Neuropharmacology
6606:media.utoronto.ca
5962:J. Med. Microbiol
5919:10.3390/ph7050545
5676:(7480): 451–455.
5621:(7480): 446–450.
5331:(7728): 589–594.
5101:cite encyclopedia
4750:10.3390/nu7042839
4535:978-0-85186-884-4
4093:978-0-7167-1007-3
4078:Biology of Plants
4036:(11): 2191–2201.
3845:10.3390/nu9121348
3790:(10): 2070–2075.
3720:Annales de chimie
3659:Sigma-Aldrich Co.
3581:978-1-4200-9084-0
3566:(90th ed.).
3526:(12): 1240–1244.
3490:978-0-85404-182-4
3374:4-Oxobutyric acid
3368:3-Oxobutyric acid
3362:2-Oxobutyric acid
3321:Histone acetylase
3226:of butyric acid.
3034:colorectal cancer
2997:Similar to other
2926:colorectal cancer
2513:
2512:
2248:(number 08.005).
2235:cellulose acetate
1969:
1968:
1943:phosphobutyrylase
1938:butyryl phosphate
1772:acetyl coenzyme A
1494:parts per million
1486:parts per billion
1250:Chemical compound
1248:
1247:
1214:Related compounds
1177:Safety data sheet
1028:Hazard statements
813:Crystal structure
801:1.426 cP (25 °C)
755:−55.10·10 cm/mol
698:0.112 kPa (20 °C)
574:Colorless liquid
432:CompTox Dashboard
152:Interactive image
89:Propylformic acid
52:
51:
16:Chemical compound
8565:
8448:
8391:Sodium valproate
8363:
8318:
8314:
8286:
8264:
8260:
8254:
8175:
8171:
8059:
8055:
8049:
8027:
8023:
8014:
8007:
8000:
7991:
7915:Sodium valproate
7742:
7735:
7728:
7719:
7686:ω−12 Unsaturated
7667:ω−11 Unsaturated
7648:ω−10 Unsaturated
7351:Eicosapentaenoic
7345:Eicosatetraenoic
7309:Palmitolinolenic
7303:Myristolinolenic
7218:Hexatriacontylic
6993:
6986:
6979:
6970:
6951:
6950:
6940:
6916:
6910:
6909:
6891:
6859:
6853:
6852:
6842:
6810:
6801:
6800:
6790:
6762:
6756:
6755:
6745:
6713:
6707:
6706:
6696:
6681:Gastroenterology
6672:
6666:
6665:
6647:
6623:
6617:
6616:
6614:
6612:
6598:
6592:
6591:
6563:
6557:
6556:
6546:
6514:
6508:
6507:
6471:
6465:
6464:
6454:
6444:
6412:
6406:
6405:
6395:
6371:
6365:
6364:
6346:
6336:
6318:
6309:
6303:
6302:
6292:
6282:
6258:
6252:
6251:
6241:
6209:
6203:
6202:
6179:Metab. Clin. Exp
6174:
6168:
6167:
6157:
6125:
6119:
6118:
6090:
6084:
6083:
6073:
6056:(12): G1405–15.
6041:
6035:
6034:
6024:
5992:
5986:
5985:
5956:
5950:
5941:
5931:
5921:
5897:
5884:
5883:
5873:
5842:The ISME Journal
5833:
5827:
5826:
5816:
5775:
5769:
5768:
5758:
5718:
5712:
5711:
5701:
5661:
5655:
5654:
5610:
5604:
5603:
5593:
5569:
5563:
5562:
5522:
5516:
5515:
5505:
5495:
5471:
5465:
5464:
5454:
5444:
5420:
5414:
5413:
5388:(8): 6229–6237.
5375:
5369:
5368:
5358:
5348:
5316:
5310:
5309:
5299:
5275:
5269:
5268:
5243:(9): 1513–1521.
5232:
5226:
5225:
5223:
5221:
5206:
5200:
5199:
5189:
5149:
5143:
5142:
5140:
5138:
5123:
5117:
5116:
5110:
5106:
5104:
5096:
5094:
5092:
5079:
5070:
5069:
5055:
5032:Curr. Pharm. Des
5023:
5014:
5013:
4999:
4970:Tsuji A (2005).
4967:
4961:
4960:
4954:
4952:
4909:
4903:
4902:
4892:
4860:
4841:
4836:
4826:
4816:
4792:
4777:
4776:
4762:
4752:
4728:
4717:
4716:
4714:
4712:
4697:
4688:
4687:
4685:
4683:
4668:
4655:
4642:
4636:
4635:
4607:
4601:
4600:, nutrabaits.net
4588:
4582:
4581:
4579:
4577:
4561:
4555:
4554:
4546:
4540:
4539:
4513:
4507:
4506:
4488:
4473:Gastroenterology
4464:
4458:
4457:
4431:
4407:
4401:
4400:
4398:
4396:
4385:
4379:
4378:
4368:
4358:
4334:
4325:
4324:
4314:
4290:
4284:
4283:
4273:
4249:
4243:
4242:
4232:
4208:
4199:
4198:
4174:
4168:
4167:
4157:
4147:
4130:(6): 2128–2133.
4111:
4105:
4104:
4102:
4100:
4081:
4068:
4062:
4061:
4025:
4019:
4018:
4016:
4014:
3998:
3989:
3988:
3978:
3954:
3945:
3944:
3942:
3940:
3926:
3920:
3919:
3909:
3877:
3868:
3867:
3857:
3847:
3823:
3814:
3808:
3802:
3801:
3799:
3775:
3769:
3758:
3752:
3735:Chevreul (1817)
3733:
3727:
3714:Chevreul (1815)
3712:
3706:
3705:
3677:
3666:
3656:
3641:
3640:
3638:
3636:
3625:
3614:
3601:
3586:
3585:
3557:
3544:
3543:
3517:
3508:
3495:
3494:
3464:
3455:
3434:
3432:
3431:
3416:
3405:
3357:Oxobutyric acids
3220:carboxylate salt
3216:physiological pH
3209:
3165:long-term memory
3154:
3150:
3104:colonic bacteria
3080:by inactivating
3003:
2957:
2919:
2893:
2862:
2809:
2777:
2772:anticarcinogenic
2736:
2626:Pharmacokinetics
2609:by reducing the
2593:. It is also an
2560:
2550:
2530:physiological pH
2520:Butyric acid (pK
2516:Pharmacodynamics
2502:
2305:
2293:Inhibited enzyme
2290:
2219:butyryl chloride
2167:brussels sprouts
2147:dandelion leaves
2064:colonic bacteria
2048:resistant starch
1921:
1852:
1841:
1803:
1799:
1788:
1662:
1634:calcium chloride
1627:
1626:
1625:
1622:
1617:
1569:hydroformylation
1548:Pastinaca sativa
1531:
1521:
1389:
1335:
1315:chemical formula
1301:
1293:
1292:
1289:
1288:
1285:
1282:
1279:
1276:
1273:
1270:
1267:
1264:
1197:carboxylic acids
1141:Explosive limits
1106:
1099:
1092:
1077:
1057:
1053:
1049:
1035:
1007:
971:
944:
917:
893:
878:Thermochemistry
840:Lattice constant
772:Refractive index
700:0.74 kPa (50 °C)
565:
552:
550:
549:
541:
540:
527:Chemical formula
457:
456:
440:
438:
412:
375:
367:
355:
344:
327:
306:
276:
268:
257:
246:
225:
217:
196:
175:
154:
129:
121:
85:Ethylacetic acid
61:
28:
24:
8573:
8572:
8568:
8567:
8566:
8564:
8563:
8562:
8518:
8517:
8516:
8511:
8498:
8464:
8435:
8381:Rosmarinic acid
8316:
8306:
8284:
8262:
8239:
8173:
8163:
8057:
8038:
8025:
8018:
7988:
7983:
7969:
7900:Sodium butyrate
7780:Allyl mercaptan
7751:
7746:
7716:
7711:
7680:
7661:
7642:
7589:ω−9 Unsaturated
7583:
7546:ω−7 Unsaturated
7540:
7505:Dihomo-linoleic
7465:12-Octadecenoic
7459:8-Tetradecenoic
7451:ω−6 Unsaturated
7445:
7400:Palmitovaccenic
7386:ω−5 Unsaturated
7380:
7363:Docosahexaenoic
7297:Myristolinoleic
7291:Myristovaccenic
7253:ω−3 Unsaturated
7247:
7188:Hentriacontylic
7006:
6997:
6960:
6955:
6954:
6918:
6917:
6913:
6861:
6860:
6856:
6812:
6811:
6804:
6764:
6763:
6759:
6734:10.1038/nrn3111
6728:(11): 623–637.
6715:
6714:
6710:
6674:
6673:
6669:
6625:
6624:
6620:
6610:
6608:
6600:
6599:
6595:
6565:
6564:
6560:
6516:
6515:
6511:
6473:
6472:
6468:
6414:
6413:
6409:
6386:(35): 36680–8.
6373:
6372:
6368:
6316:
6311:
6310:
6306:
6260:
6259:
6255:
6211:
6210:
6206:
6176:
6175:
6171:
6127:
6126:
6122:
6092:
6091:
6087:
6043:
6042:
6038:
6007:(6): 2897–904.
5994:
5993:
5989:
5968:(Pt 4): 582–9.
5958:
5957:
5953:
5946:
5942:
5906:Pharmaceuticals
5900:Wang G (2014).
5899:
5898:
5887:
5835:
5834:
5830:
5777:
5776:
5772:
5720:
5719:
5715:
5663:
5662:
5658:
5612:
5611:
5607:
5571:
5570:
5566:
5524:
5523:
5519:
5473:
5472:
5468:
5422:
5421:
5417:
5377:
5376:
5372:
5318:
5317:
5313:
5277:
5276:
5272:
5234:
5233:
5229:
5219:
5217:
5208:
5207:
5203:
5158:Cell Metabolism
5151:
5150:
5146:
5136:
5134:
5125:
5124:
5120:
5107:
5097:
5090:
5088:
5081:
5080:
5073:
5038:(10): 1487–98.
5025:
5024:
5017:
4969:
4968:
4964:
4950:
4948:
4911:
4910:
4906:
4862:
4861:
4844:
4837:
4794:
4793:
4780:
4730:
4729:
4720:
4710:
4708:
4699:
4698:
4691:
4681:
4679:
4670:
4669:
4658:
4652:Wayback Machine
4643:
4639:
4609:
4608:
4604:
4598:Wayback Machine
4589:
4585:
4575:
4573:
4570:WAAC Newsletter
4563:
4562:
4558:
4548:
4547:
4543:
4536:
4515:
4514:
4510:
4466:
4465:
4461:
4409:
4408:
4404:
4394:
4392:
4387:
4386:
4382:
4336:
4335:
4328:
4292:
4291:
4287:
4251:
4250:
4246:
4210:
4209:
4202:
4176:
4175:
4171:
4116:"The Genome of
4113:
4112:
4108:
4098:
4096:
4094:
4072:Raven, Peter H.
4070:
4069:
4065:
4027:
4026:
4022:
4012:
4010:
4000:
3999:
3992:
3956:
3955:
3948:
3938:
3936:
3928:
3927:
3923:
3879:
3878:
3871:
3825:
3824:
3817:
3809:
3805:
3777:
3776:
3772:
3759:
3755:
3734:
3730:
3713:
3709:
3702:
3679:
3678:
3669:
3657:
3644:
3634:
3632:
3629:"Butanoic acid"
3627:
3626:
3617:
3602:
3589:
3582:
3559:
3558:
3547:
3515:
3510:
3509:
3498:
3491:
3466:
3465:
3461:
3444:, ed. (1911). "
3440:
3429:
3427:
3425:
3420:
3419:
3406:
3402:
3397:
3297:
3284:Pentyl butyrate
3279:Methyl butyrate
3265:(aircraft dope)
3249:
3241:Sodium butyrate
3237:
3232:
3203:
3197:
3191:
3177:
3152:
3144:
3123:
3089:gene expression
3022:
3006:vascular tissue
3002:
2998:
2988:immune response
2944:gene expression
2918:
2914:
2892:
2888:
2876:
2861:
2857:
2817:
2808:
2804:
2794:targets (i.e.,
2764:immune function
2744:
2734:
2730:
2668:
2628:
2591:
2557:
2552:
2549:
2545:
2524:4.82) is fully
2523:
2518:
2501:
2497:
2461:
2300:
2285:
2257:Cyprinus carpio
2246:FLAVIS database
2242:methyl butyrate
2227:
2199:
2131:globe artichoke
2044:
1964:butyrate kinase
1919:
1915:
1911:
1907:
1840:
1836:
1832:
1828:
1824:
1820:
1816:
1812:
1808:
1798:
1794:
1787:
1783:
1669:
1660:
1653:
1649:
1645:
1641:
1637:
1623:
1620:
1619:
1618:
1615:
1611:
1607:
1603:
1599:
1595:
1591:
1565:
1560:
1528:
1523:
1520:
1516:
1502:flavoring agent
1450:parmesan cheese
1423:carboxylic acid
1404:
1382:Henri Braconnot
1370:
1342:Isobutyric acid
1338:unpleasant odor
1333:
1329:
1325:
1321:
1317:
1311:carboxylic acid
1261:
1257:
1251:
1244:
1239:
1227:Methyl butyrate
1225:
1221:
1215:
1199:
1168:
1162:
1132:
1129:
1111:
1110:
1109:
1108:
1101:
1094:
1087:
1083:
1075:
1044:
1030:
1016:
1000:
972:
969:
963:
959:
956:
955:Std enthalpy of
945:
942:
936:
932:
929:
928:Std enthalpy of
918:
915:
908:
905:
894:
887:
873:0.93 D (20 °C)
870:
861:
858:
842:
830:
815:
800:
782:
780:
752:
738:
721:
719:
710:
701:
699:
674:
648:
635:
631:
627:
624:
595:
563:
548:
545:
544:
543:
539:
536:
535:
534:
532:
529:
515:
512:
507:
506:
495:
492:
491:
488:
482:
481:
478:
472:
471:
460:
441:
434:
415:
394:
378:
370:Butyrate:
356:
330:
309:
295:
286:
249:
228:
220:Butyrate:
199:
178:
157:
143:
132:
124:Butyrate:
110:
96:
90:
88:
86:
78:
77:
17:
12:
11:
5:
8571:
8569:
8561:
8560:
8555:
8550:
8545:
8540:
8538:Alkanoic acids
8535:
8530:
8528:GABA analogues
8520:
8519:
8513:
8512:
8510:
8509:
8502:
8496:
8491:
8484:
8477:
8473:
8470:
8469:
8466:
8465:
8463:
8462:
8456:
8454:
8452:Antivitamin B6
8445:
8441:
8440:
8437:
8436:
8434:
8433:
8424:
8423:
8418:
8413:
8408:
8403:
8398:
8393:
8388:
8378:
8373:
8368:
8360:
8355:
8350:
8345:
8340:
8335:
8330:
8321:
8319:
8308:
8307:
8305:
8304:
8295:
8294:
8289:
8281:
8276:
8267:
8265:
8251:
8245:
8244:
8241:
8240:
8238:
8237:
8232:
8227:
8225:Nipecotic acid
8222:
8217:
8215:N-Butyric acid
8212:
8207:
8202:
8197:
8192:
8190:Bafilomycin A1
8187:
8178:
8176:
8165:
8164:
8162:
8161:
8156:
8151:
8146:
8141:
8136:
8131:
8126:
8124:Nipecotic acid
8121:
8116:
8111:
8106:
8101:
8096:
8091:
8086:
8081:
8076:
8071:
8062:
8060:
8046:
8040:
8039:
8019:
8017:
8016:
8009:
8002:
7994:
7985:
7984:
7974:
7971:
7970:
7968:
7967:
7962:
7957:
7952:
7947:
7942:
7937:
7932:
7930:Trichostatin A
7927:
7922:
7917:
7912:
7907:
7902:
7897:
7892:
7887:
7882:
7877:
7872:
7870:Phenylbutyrate
7867:
7862:
7857:
7852:
7847:
7842:
7837:
7832:
7827:
7822:
7817:
7812:
7807:
7802:
7797:
7792:
7787:
7782:
7777:
7772:
7767:
7762:
7756:
7753:
7752:
7747:
7745:
7744:
7737:
7730:
7722:
7713:
7712:
7710:
7709:
7703:
7697:
7694:4-Hexadecenoic
7690:
7688:
7682:
7681:
7679:
7678:
7671:
7669:
7663:
7662:
7660:
7659:
7652:
7650:
7644:
7643:
7641:
7640:
7634:
7628:
7622:
7616:
7610:
7600:
7593:
7591:
7585:
7584:
7582:
7581:
7575:
7569:
7563:
7557:
7550:
7548:
7542:
7541:
7539:
7538:
7532:
7526:
7520:
7514:
7508:
7502:
7496:
7490:
7484:
7474:
7468:
7462:
7455:
7453:
7447:
7446:
7444:
7443:
7437:
7431:
7425:
7419:
7409:
7403:
7397:
7390:
7388:
7382:
7381:
7379:
7378:
7372:
7366:
7360:
7354:
7348:
7342:
7336:
7330:
7324:
7318:
7312:
7306:
7300:
7294:
7288:
7282:
7276:
7270:
7264:
7257:
7255:
7249:
7248:
7246:
7245:
7242:Tetracontanoic
7239:
7233:
7227:
7221:
7215:
7209:
7203:
7197:
7191:
7185:
7179:
7173:
7167:
7161:
7155:
7149:
7143:
7137:
7131:
7125:
7119:
7113:
7107:
7101:
7095:
7089:
7083:
7077:
7071:
7065:
7059:
7053:
7047:
7041:
7035:
7029:
7023:
7016:
7014:
7008:
7007:
6998:
6996:
6995:
6988:
6981:
6973:
6967:
6966:
6959:
6958:External links
6956:
6953:
6952:
6911:
6854:
6802:
6757:
6708:
6667:
6638:(2): 288–299.
6618:
6593:
6558:
6509:
6482:(3): 465–478.
6466:
6407:
6366:
6304:
6253:
6204:
6185:(2): 102–113.
6169:
6120:
6101:(4): 245–255.
6095:Trends Mol Med
6085:
6036:
5987:
5951:
5885:
5848:(4): 832–843.
5828:
5770:
5713:
5656:
5605:
5584:(3): 785–796.
5564:
5517:
5466:
5435:(4): 269–276.
5415:
5370:
5311:
5270:
5227:
5201:
5164:(5): 517–526.
5144:
5118:
5109:|website=
5071:
5015:
4962:
4904:
4869:Neurosci. Lett
4842:
4778:
4743:(4): 2839–49.
4718:
4689:
4672:"Butyric acid"
4656:
4637:
4618:(4): 289–347.
4602:
4583:
4556:
4541:
4534:
4508:
4459:
4422:(2): 252–258.
4402:
4380:
4326:
4305:(9): 3244–57.
4285:
4244:
4200:
4189:(8): 835–843.
4169:
4106:
4092:
4063:
4020:
3990:
3946:
3930:"Butyric acid"
3921:
3892:(3): 189–200.
3869:
3815:
3803:
3770:
3753:
3728:
3707:
3701:978-3527306732
3700:
3667:
3642:
3615:
3587:
3580:
3545:
3496:
3489:
3458:
3457:
3442:Chisholm, Hugh
3424:
3421:
3418:
3417:
3399:
3398:
3396:
3393:
3392:
3391:
3390:
3389:
3379:
3378:
3377:
3371:
3365:
3354:
3353:
3352:
3347:
3342:
3332:
3331:
3330:
3329:
3328:
3323:
3308:
3303:
3296:
3293:
3292:
3291:
3286:
3281:
3276:
3274:Ethyl butyrate
3271:
3266:
3260:
3255:
3253:Butyl butyrate
3248:
3245:
3244:
3243:
3236:
3233:
3231:
3228:
3212:conjugate base
3176:
3173:
3143:
3140:
3122:
3119:
3115:MSH2-deficient
3046:Warburg effect
3044:cells, is the
3021:
3018:
3010:neuropeptide Y
2968:interleukin 10
2875:
2872:
2816:
2813:
2743:
2740:
2739:
2738:
2684:
2683:
2667:
2664:
2627:
2624:
2595:HDAC inhibitor
2589:
2555:
2521:
2517:
2514:
2511:
2510:
2507:
2504:
2493:
2492:
2489:
2486:
2480:
2479:
2476:
2473:
2467:
2466:
2463:
2459:
2455:
2448:
2447:
2445:
2442:
2436:
2435:
2433:
2430:
2424:
2423:
2420:
2417:
2411:
2410:
2408:
2405:
2399:
2398:
2395:
2392:
2386:
2385:
2382:
2379:
2373:
2372:
2369:
2366:
2360:
2359:
2356:
2353:
2347:
2346:
2344:
2341:
2335:
2334:
2332:
2329:
2323:
2322:
2320:
2317:
2311:
2310:
2307:
2298:
2294:
2284:
2281:
2226:
2223:
2198:
2195:
2089:, such as the
2043:
2040:
2032:
2031:
2028:
2014:
2013:
2006:
1999:
1992:
1967:
1966:
1961:
1946:
1945:
1940:
1929:
1928:
1923:
1899:
1898:
1893:
1886:
1885:
1880:
1873:
1872:
1867:
1860:
1859:
1856:
1843:
1842:
1780:carbon dioxide
1748:
1747:
1742:
1735:
1728:
1721:
1714:
1707:
1676:dehydrogenase.
1668:
1665:
1630:
1629:
1564:
1561:
1559:
1556:
1526:
1403:
1400:
1398:) is similar.
1369:
1366:
1249:
1246:
1245:
1240:
1236:standard state
1233:
1230:
1229:
1216:
1213:
1210:
1209:
1207:Pentanoic acid
1203:Propionic acid
1200:
1194:
1191:
1190:
1186:
1185:
1180:
1173:
1172:
1169:
1160:
1158:
1155:
1154:
1147:
1146:
1143:
1137:
1136:
1133:
1126:
1123:
1122:
1119:
1113:
1112:
1102:
1095:
1088:
1073:
1072:
1071:
1070:
1068:
1059:
1058:
1052:P305+P351+P338
1045:
1040:
1037:
1036:
1031:
1026:
1023:
1022:
1017:
1012:
1009:
1008:
1001:
996:
993:
992:
982:
981:
977:
976:
975:2183.5 kJ/mol
973:
967:
961:
953:
950:
949:
948:−533.9 kJ/mol
946:
940:
934:
926:
923:
922:
921:222.2 J/mol·K
919:
913:
902:
899:
898:
897:178.6 J/mol·K
895:
883:
880:
879:
875:
874:
871:
866:
863:
862:
859:
845:
843:
838:
835:
834:
831:
826:
823:
822:
816:
811:
808:
807:
803:
802:
793:
787:
786:
785:1.398 (20 °C)
783:
778:
770:
767:
766:
765:1.46·10 W/m·K
763:
757:
756:
753:
747:
744:
743:
740:
736:
726:
725:
722:
717:
707:
704:
703:
696:
694:Vapor pressure
690:
689:
686:
677:
676:
672:
661:Miscible with
659:
653:
652:
649:
644:
641:
640:
633:
628:
621:
618:
617:
614:
608:
607:
604:
598:
597:
592:
586:
585:
582:
576:
575:
572:
568:
567:
561:
555:
554:
546:
537:
530:
525:
522:
521:
517:
516:
514:
513:
510:
502:
501:
500:
497:
496:
494:
493:
489:
486:
485:
483:
479:
476:
475:
467:
466:
465:
462:
461:
459:
458:
444:
442:
430:
427:
426:
423:
417:
416:
414:
413:
404:
402:
396:
395:
393:
392:
388:
386:
380:
379:
377:
376:
368:
359:
357:
349:
346:
345:
338:
332:
331:
329:
328:
319:
317:
311:
310:
308:
307:
298:
296:
291:
288:
287:
285:
284:
280:
278:
270:
269:
259:
251:
250:
248:
247:
238:
236:
230:
229:
227:
226:
218:
209:
207:
201:
200:
198:
197:
188:
186:
180:
179:
177:
176:
167:
165:
159:
158:
156:
155:
146:
144:
137:
134:
133:
131:
130:
122:
113:
111:
106:
103:
102:
98:
97:
84:
80:
79:
75:
74:
68:
67:
63:
62:
54:
53:
50:
49:
39:
15:
13:
10:
9:
6:
4:
3:
2:
8570:
8559:
8556:
8554:
8551:
8549:
8546:
8544:
8541:
8539:
8536:
8534:
8531:
8529:
8526:
8525:
8523:
8508:
8507:
8503:
8501:
8500:
8492:
8490:
8489:
8485:
8483:
8482:
8478:
8475:
8474:
8471:
8461:
8458:
8457:
8455:
8453:
8449:
8446:
8442:
8432:
8431:3-Methyl-GABA
8429:
8426:
8425:
8422:
8419:
8417:
8414:
8412:
8411:Valproic acid
8409:
8407:
8404:
8402:
8399:
8397:
8394:
8392:
8389:
8386:
8382:
8379:
8377:
8374:
8372:
8369:
8367:
8361:
8359:
8356:
8354:
8351:
8349:
8346:
8344:
8341:
8339:
8336:
8334:
8331:
8329:
8326:
8323:
8322:
8320:
8315:
8309:
8303:
8302:3-Methyl-GABA
8300:
8297:
8296:
8293:
8292:Semicarbazide
8290:
8288:
8287:-Allylglycine
8282:
8280:
8277:
8275:
8272:
8269:
8268:
8266:
8261:
8255:
8252:
8250:
8246:
8236:
8233:
8231:
8228:
8226:
8223:
8221:
8218:
8216:
8213:
8211:
8208:
8206:
8203:
8201:
8198:
8196:
8193:
8191:
8188:
8186:
8183:
8180:
8179:
8177:
8172:
8166:
8160:
8157:
8155:
8152:
8150:
8147:
8145:
8142:
8140:
8137:
8135:
8132:
8130:
8127:
8125:
8122:
8120:
8117:
8115:
8114:Ibotenic acid
8112:
8110:
8107:
8105:
8102:
8100:
8097:
8095:
8092:
8090:
8087:
8085:
8082:
8080:
8077:
8075:
8072:
8070:
8067:
8064:
8063:
8061:
8056:
8050:
8047:
8045:
8041:
8037:
8034:
8030:
8024:
8015:
8010:
8008:
8003:
8001:
7996:
7995:
7992:
7982:
7981:
7978:
7972:
7966:
7963:
7961:
7958:
7956:
7953:
7951:
7948:
7946:
7943:
7941:
7938:
7936:
7933:
7931:
7928:
7926:
7923:
7921:
7918:
7916:
7913:
7911:
7908:
7906:
7903:
7901:
7898:
7896:
7893:
7891:
7888:
7886:
7883:
7881:
7878:
7876:
7873:
7871:
7868:
7866:
7863:
7861:
7858:
7856:
7853:
7851:
7848:
7846:
7843:
7841:
7838:
7836:
7833:
7831:
7828:
7826:
7823:
7821:
7818:
7816:
7813:
7811:
7808:
7806:
7803:
7801:
7798:
7796:
7793:
7791:
7788:
7786:
7783:
7781:
7778:
7776:
7773:
7771:
7768:
7766:
7763:
7761:
7758:
7757:
7754:
7750:
7743:
7738:
7736:
7731:
7729:
7724:
7723:
7720:
7707:
7704:
7701:
7698:
7695:
7692:
7691:
7689:
7687:
7683:
7676:
7673:
7672:
7670:
7668:
7664:
7657:
7654:
7653:
7651:
7649:
7645:
7638:
7635:
7632:
7629:
7626:
7623:
7620:
7617:
7614:
7611:
7608:
7604:
7601:
7598:
7595:
7594:
7592:
7590:
7586:
7579:
7576:
7573:
7570:
7567:
7564:
7561:
7558:
7555:
7552:
7551:
7549:
7547:
7543:
7536:
7533:
7530:
7527:
7524:
7521:
7518:
7515:
7512:
7509:
7506:
7503:
7500:
7497:
7494:
7491:
7488:
7485:
7482:
7478:
7475:
7472:
7469:
7466:
7463:
7460:
7457:
7456:
7454:
7452:
7448:
7441:
7438:
7435:
7432:
7429:
7426:
7423:
7420:
7417:
7413:
7412:β-Eleostearic
7410:
7407:
7406:α-Eleostearic
7404:
7401:
7398:
7395:
7392:
7391:
7389:
7387:
7383:
7376:
7373:
7370:
7367:
7364:
7361:
7358:
7355:
7352:
7349:
7346:
7343:
7340:
7337:
7334:
7331:
7328:
7325:
7322:
7319:
7316:
7313:
7310:
7307:
7304:
7301:
7298:
7295:
7292:
7289:
7286:
7285:Laurolinoleic
7283:
7280:
7277:
7274:
7271:
7268:
7265:
7262:
7259:
7258:
7256:
7254:
7250:
7243:
7240:
7237:
7234:
7231:
7228:
7225:
7222:
7219:
7216:
7213:
7210:
7207:
7204:
7201:
7198:
7195:
7192:
7189:
7186:
7183:
7180:
7177:
7174:
7171:
7168:
7165:
7162:
7159:
7156:
7153:
7150:
7147:
7144:
7141:
7138:
7135:
7132:
7129:
7126:
7123:
7120:
7117:
7114:
7111:
7108:
7105:
7102:
7099:
7096:
7093:
7090:
7087:
7084:
7081:
7078:
7075:
7072:
7069:
7066:
7063:
7060:
7057:
7054:
7051:
7048:
7045:
7042:
7039:
7036:
7033:
7030:
7027:
7024:
7021:
7018:
7017:
7015:
7013:
7009:
7005:
7001:
6994:
6989:
6987:
6982:
6980:
6975:
6974:
6971:
6965:
6962:
6961:
6957:
6948:
6944:
6939:
6934:
6930:
6927:(in French).
6926:
6922:
6915:
6912:
6907:
6903:
6899:
6895:
6890:
6885:
6881:
6877:
6873:
6869:
6865:
6858:
6855:
6850:
6846:
6841:
6836:
6832:
6828:
6824:
6820:
6816:
6809:
6807:
6803:
6798:
6794:
6789:
6784:
6780:
6776:
6772:
6768:
6761:
6758:
6753:
6749:
6744:
6739:
6735:
6731:
6727:
6723:
6719:
6712:
6709:
6704:
6700:
6695:
6690:
6686:
6682:
6678:
6671:
6668:
6663:
6659:
6655:
6651:
6646:
6641:
6637:
6633:
6629:
6622:
6619:
6607:
6603:
6597:
6594:
6589:
6585:
6581:
6577:
6573:
6569:
6562:
6559:
6554:
6550:
6545:
6540:
6536:
6532:
6528:
6524:
6520:
6513:
6510:
6505:
6501:
6497:
6493:
6489:
6485:
6481:
6477:
6470:
6467:
6462:
6458:
6453:
6448:
6443:
6438:
6434:
6430:
6426:
6422:
6418:
6411:
6408:
6403:
6399:
6394:
6389:
6385:
6381:
6377:
6370:
6367:
6362:
6358:
6354:
6350:
6345:
6340:
6335:
6330:
6326:
6322:
6315:
6308:
6305:
6300:
6296:
6291:
6286:
6281:
6276:
6272:
6268:
6264:
6257:
6254:
6249:
6245:
6240:
6235:
6231:
6227:
6224:(3): 603–27.
6223:
6219:
6215:
6208:
6205:
6200:
6196:
6192:
6188:
6184:
6180:
6173:
6170:
6165:
6161:
6156:
6151:
6147:
6143:
6139:
6135:
6131:
6124:
6121:
6116:
6112:
6108:
6104:
6100:
6096:
6089:
6086:
6081:
6077:
6072:
6067:
6063:
6059:
6055:
6051:
6047:
6040:
6037:
6032:
6028:
6023:
6018:
6014:
6010:
6006:
6002:
5998:
5991:
5988:
5983:
5979:
5975:
5971:
5967:
5963:
5955:
5952:
5949:
5945:
5939:
5935:
5930:
5925:
5920:
5915:
5912:(5): 545–94.
5911:
5907:
5903:
5896:
5894:
5892:
5890:
5886:
5881:
5877:
5872:
5867:
5863:
5859:
5855:
5851:
5847:
5843:
5839:
5832:
5829:
5824:
5820:
5815:
5810:
5806:
5802:
5798:
5794:
5790:
5786:
5782:
5774:
5771:
5766:
5762:
5757:
5752:
5748:
5744:
5740:
5736:
5732:
5728:
5724:
5717:
5714:
5709:
5705:
5700:
5695:
5691:
5687:
5683:
5679:
5675:
5671:
5667:
5660:
5657:
5652:
5648:
5644:
5640:
5636:
5632:
5628:
5624:
5620:
5616:
5609:
5606:
5601:
5597:
5592:
5587:
5583:
5579:
5575:
5568:
5565:
5560:
5556:
5552:
5548:
5544:
5540:
5536:
5532:
5528:
5521:
5518:
5513:
5509:
5504:
5499:
5494:
5489:
5485:
5481:
5477:
5470:
5467:
5462:
5458:
5453:
5448:
5443:
5438:
5434:
5430:
5426:
5419:
5416:
5411:
5407:
5403:
5399:
5395:
5391:
5387:
5383:
5382:
5374:
5371:
5366:
5362:
5357:
5352:
5347:
5342:
5338:
5334:
5330:
5326:
5322:
5315:
5312:
5307:
5303:
5298:
5293:
5289:
5285:
5281:
5274:
5271:
5266:
5262:
5258:
5254:
5250:
5246:
5242:
5238:
5231:
5228:
5215:
5211:
5205:
5202:
5197:
5193:
5188:
5183:
5179:
5175:
5171:
5167:
5163:
5159:
5155:
5148:
5145:
5132:
5128:
5122:
5119:
5114:
5102:
5086:
5085:
5078:
5076:
5072:
5068:
5063:
5059:
5054:
5049:
5045:
5041:
5037:
5033:
5029:
5022:
5020:
5016:
5012:
5007:
5003:
4998:
4993:
4989:
4985:
4981:
4977:
4973:
4966:
4963:
4959:
4947:
4943:
4939:
4935:
4931:
4927:
4923:
4919:
4915:
4908:
4905:
4900:
4896:
4891:
4886:
4882:
4878:
4874:
4870:
4866:
4859:
4857:
4855:
4853:
4851:
4849:
4847:
4843:
4840:
4834:
4830:
4825:
4820:
4815:
4810:
4806:
4802:
4801:Front Immunol
4798:
4791:
4789:
4787:
4785:
4783:
4779:
4775:
4770:
4766:
4761:
4756:
4751:
4746:
4742:
4738:
4734:
4727:
4725:
4723:
4719:
4706:
4702:
4696:
4694:
4690:
4677:
4673:
4667:
4665:
4663:
4661:
4657:
4653:
4649:
4646:
4641:
4638:
4633:
4629:
4625:
4621:
4617:
4613:
4606:
4603:
4599:
4595:
4592:
4591:Freezer Baits
4587:
4584:
4571:
4567:
4560:
4557:
4552:
4545:
4542:
4537:
4531:
4527:
4523:
4519:
4512:
4509:
4504:
4500:
4496:
4492:
4487:
4482:
4478:
4474:
4470:
4463:
4460:
4455:
4451:
4447:
4443:
4439:
4435:
4430:
4425:
4421:
4417:
4413:
4406:
4403:
4390:
4384:
4381:
4376:
4372:
4367:
4362:
4357:
4352:
4348:
4344:
4340:
4333:
4331:
4327:
4322:
4318:
4313:
4308:
4304:
4300:
4296:
4289:
4286:
4281:
4277:
4272:
4267:
4263:
4259:
4255:
4248:
4245:
4240:
4236:
4231:
4226:
4223:(2): 479–82.
4222:
4218:
4214:
4207:
4205:
4201:
4196:
4192:
4188:
4184:
4180:
4173:
4170:
4165:
4161:
4156:
4151:
4146:
4141:
4137:
4133:
4129:
4125:
4121:
4119:
4110:
4107:
4095:
4089:
4085:
4080:
4079:
4073:
4067:
4064:
4059:
4055:
4051:
4047:
4043:
4039:
4035:
4031:
4024:
4021:
4008:
4004:
3997:
3995:
3991:
3986:
3982:
3977:
3972:
3969:(2): 269–90.
3968:
3964:
3960:
3953:
3951:
3947:
3935:
3931:
3925:
3922:
3917:
3913:
3908:
3903:
3899:
3895:
3891:
3887:
3883:
3876:
3874:
3870:
3865:
3861:
3856:
3851:
3846:
3841:
3837:
3833:
3829:
3822:
3820:
3816:
3812:
3807:
3804:
3798:
3793:
3789:
3785:
3781:
3774:
3771:
3767:
3766:pages 115–133
3763:
3760:E. Chevreul,
3757:
3754:
3750:
3746:
3742:
3738:
3732:
3729:
3725:
3721:
3717:
3711:
3708:
3703:
3697:
3693:
3689:
3685:
3684:
3676:
3674:
3672:
3668:
3664:
3660:
3655:
3653:
3651:
3649:
3647:
3643:
3630:
3624:
3622:
3620:
3616:
3612:
3610:
3605:
3604:Butanoic acid
3600:
3598:
3596:
3594:
3592:
3588:
3583:
3577:
3573:
3569:
3565:
3564:
3556:
3554:
3552:
3550:
3546:
3541:
3537:
3533:
3529:
3525:
3521:
3514:
3507:
3505:
3503:
3501:
3497:
3492:
3486:
3482:
3478:
3474:
3471:. Cambridge:
3470:
3463:
3460:
3456:
3453:
3452:
3447:
3443:
3438:
3437:public domain
3422:
3414:
3410:
3404:
3401:
3394:
3388:
3385:
3384:
3383:
3380:
3375:
3372:
3369:
3366:
3363:
3360:
3359:
3358:
3355:
3351:
3348:
3346:
3343:
3341:
3338:
3337:
3336:
3333:
3327:
3324:
3322:
3319:
3318:
3317:
3314:
3313:
3312:
3309:
3307:
3304:
3302:
3299:
3298:
3294:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3264:
3261:
3259:
3256:
3254:
3251:
3250:
3246:
3242:
3239:
3238:
3234:
3229:
3227:
3225:
3221:
3217:
3213:
3207:
3200:
3194:
3189:
3186:
3182:
3174:
3172:
3170:
3166:
3162:
3158:
3151:
3141:
3139:
3136:
3132:
3128:
3120:
3118:
3116:
3111:
3109:
3105:
3101:
3097:
3092:
3090:
3087:
3083:
3079:
3075:
3071:
3067:
3063:
3059:
3055:
3051:
3047:
3043:
3039:
3035:
3031:
3027:
3019:
3017:
3015:
3011:
3007:
2995:
2993:
2989:
2985:
2981:
2977:
2973:
2969:
2965:
2961:
2953:
2949:
2945:
2941:
2937:
2934:
2929:
2927:
2923:
2912:
2911:
2906:
2902:
2899:(GPR43), and
2898:
2894:
2885:
2881:
2873:
2871:
2868:
2864:
2863:
2852:
2850:
2846:
2842:
2837:
2835:
2831:
2827:
2826:dietary fiber
2823:
2814:
2812:
2810:
2801:
2797:
2793:
2789:
2785:
2781:
2773:
2769:
2768:antimicrobial
2765:
2761:
2757:
2753:
2749:
2741:
2729:Tributyrin +
2728:
2727:
2726:
2724:
2720:
2716:
2711:
2709:
2705:
2701:
2697:
2693:
2689:
2681:
2680:
2679:
2677:
2673:
2665:
2663:
2661:
2658:(FATP1), and
2657:
2653:
2649:
2645:
2641:
2637:
2633:
2625:
2623:
2620:
2616:
2612:
2611:electrostatic
2608:
2604:
2600:
2596:
2592:
2585:
2581:
2577:
2574:
2570:
2565:
2563:
2559:
2543:
2539:
2535:
2531:
2527:
2515:
2508:
2505:
2503:
2495:
2494:
2491:Full agonist
2490:
2487:
2485:
2482:
2481:
2478:Full agonist
2477:
2474:
2472:
2469:
2468:
2464:
2462:
2456:
2453:
2450:
2449:
2446:
2443:
2441:
2438:
2437:
2434:
2431:
2429:
2426:
2425:
2421:
2418:
2416:
2413:
2412:
2409:
2406:
2404:
2401:
2400:
2396:
2393:
2391:
2388:
2387:
2383:
2380:
2378:
2375:
2374:
2370:
2367:
2365:
2362:
2361:
2357:
2354:
2352:
2349:
2348:
2345:
2342:
2340:
2337:
2336:
2333:
2330:
2328:
2325:
2324:
2321:
2318:
2316:
2313:
2312:
2308:
2301:
2295:
2292:
2291:
2282:
2280:
2278:
2274:
2270:
2266:
2262:
2258:
2254:
2249:
2247:
2243:
2238:
2236:
2232:
2224:
2222:
2220:
2216:
2212:
2208:
2204:
2196:
2194:
2192:
2188:
2187:oligofructose
2184:
2180:
2176:
2172:
2168:
2164:
2160:
2156:
2152:
2148:
2144:
2140:
2136:
2132:
2128:
2124:
2120:
2116:
2112:
2108:
2104:
2100:
2096:
2092:
2088:
2083:
2081:
2077:
2076:dietary fiber
2073:
2069:
2065:
2061:
2057:
2053:
2049:
2041:
2039:
2037:
2029:
2026:
2025:
2024:
2021:
2019:
2012:
2011:
2007:
2005:
2004:
2000:
1998:
1997:
1993:
1990:
1989:
1985:
1984:
1983:
1981:
1979:
1974:
1965:
1962:
1960:
1956:
1952:
1948:
1947:
1944:
1941:
1939:
1935:
1931:
1930:
1927:
1924:
1905:
1901:
1900:
1897:
1894:
1892:
1888:
1887:
1884:
1881:
1879:
1875:
1874:
1871:
1868:
1866:
1862:
1861:
1857:
1854:
1853:
1850:
1848:
1807:
1806:
1805:
1792:
1781:
1777:
1774:catalyzed by
1773:
1769:
1765:
1761:
1757:
1753:
1746:
1743:
1741:
1740:
1736:
1734:
1733:
1729:
1727:
1726:
1722:
1720:
1719:
1715:
1713:
1712:
1708:
1706:
1705:
1701:
1700:
1699:
1698:of bacteria:
1697:
1693:
1692:Louis Pasteur
1689:
1686:
1683:
1673:
1666:
1664:
1656:
1635:
1590:
1589:
1588:
1586:
1582:
1581:butyraldehyde
1578:
1574:
1570:
1562:
1557:
1555:
1553:
1549:
1545:
1541:
1536:
1534:
1530:
1514:
1510:
1505:
1503:
1499:
1495:
1491:
1487:
1483:
1479:
1475:
1471:
1467:
1463:
1459:
1455:
1451:
1447:
1443:
1439:
1436:
1432:
1428:
1424:
1420:
1416:
1412:
1408:
1407:Triglycerides
1401:
1399:
1397:
1393:
1388:
1383:
1379:
1375:
1367:
1365:
1363:
1359:
1355:
1351:
1347:
1343:
1339:
1316:
1312:
1309:
1305:
1304:butanoic acid
1297:
1296:Ancient Greek
1291:
1255:
1243:
1237:
1231:
1228:
1224:
1223:Butyraldehyde
1220:
1217:
1212:
1211:
1208:
1204:
1201:
1198:
1193:
1192:
1187:
1184:
1183:External MSDS
1181:
1178:
1175:
1174:
1170:
1166:
1157:
1156:
1152:
1148:
1144:
1142:
1139:
1138:
1134:
1131:
1125:
1124:
1120:
1118:
1115:
1114:
1107:
1100:
1093:
1069:
1066:
1065:
1061:
1060:
1046:
1043:
1039:
1038:
1032:
1029:
1025:
1024:
1021:
1018:
1015:
1011:
1010:
1006:
1002:
999:
995:
994:
990:
988:
983:
978:
974:
966:
958:
952:
951:
947:
939:
931:
925:
924:
920:
912:
907:
901:
900:
896:
891:
886:
885:Heat capacity
882:
881:
876:
872:
869:
868:Dipole moment
865:
864:
856:
852:
848:
844:
841:
837:
836:
832:
829:
825:
824:
820:
817:
814:
810:
809:
804:
798:
794:
792:
789:
788:
784:
777:
773:
769:
768:
764:
762:
759:
758:
754:
750:
746:
745:
741:
735:
731:
728:
727:
723:
716:
712:
706:
705:
697:
695:
692:
691:
687:
685:
684:
679:
678:
675:
668:
664:
660:
658:
655:
654:
650:
647:
643:
642:
638:
629:
626:
620:
619:
615:
613:
612:Boiling point
610:
609:
605:
603:
602:Melting point
600:
599:
593:
591:
588:
587:
583:
581:
578:
577:
573:
570:
569:
562:
560:
557:
556:
531:
528:
524:
523:
518:
509:
505:
498:
484:
474:
470:
463:
455:
451:
450:DTXSID8021515
446:
445:
443:
433:
429:
428:
424:
422:
419:
418:
411:
406:
405:
403:
401:
398:
397:
390:
389:
387:
385:
382:
381:
374:
369:
366:
361:
360:
358:
352:
348:
347:
343:
339:
337:
334:
333:
326:
321:
320:
318:
316:
313:
312:
305:
300:
299:
297:
294:
290:
289:
282:
281:
279:
277:
272:
271:
267:
263:
260:
258:
256:ECHA InfoCard
253:
252:
245:
240:
239:
237:
235:
232:
231:
224:
219:
216:
211:
210:
208:
206:
203:
202:
195:
190:
189:
187:
185:
182:
181:
174:
169:
168:
166:
164:
161:
160:
153:
148:
147:
145:
141:
136:
135:
128:
123:
120:
115:
114:
112:
109:
105:
104:
99:
94:
93:Lipid numbers
81:
76:Butanoic acid
73:
69:
64:
60:
55:
44:
40:
34:
30:
29:
25:
22:Butyric acid
19:
8553:Biomolecules
8504:
8493:
8486:
8479:
8427:
8396:Valnoctamide
8366:-Cycloserine
8324:
8298:
8270:
8181:
8065:
7976:
7975:
7940:Valnoctamide
7935:Tucidinostat
7920:Sulforaphane
7865:Parthenolide
7860:Panobinostat
7850:Mocetinostat
7825:Fimepinostat
7805:Citarinostat
7794:
7706:8-Eicosenoic
7700:Petroselinic
7606:
7480:
7477:Linolelaidic
7415:
7357:Clupanodonic
7315:Palmitidonic
7152:Pentacosylic
7128:Heneicosylic
7092:Pentadecylic
7025:
6931:(1): 83–91.
6928:
6924:
6914:
6871:
6867:
6857:
6822:
6818:
6770:
6760:
6725:
6721:
6711:
6687:(1): 51–56.
6684:
6680:
6670:
6635:
6631:
6621:
6609:. Retrieved
6605:
6596:
6574:(1): 85–95.
6571:
6567:
6561:
6526:
6522:
6512:
6479:
6475:
6469:
6427:(8): e6759.
6424:
6420:
6410:
6383:
6379:
6369:
6324:
6320:
6307:
6273:(2): 41–51.
6270:
6266:
6256:
6221:
6217:
6207:
6182:
6178:
6172:
6137:
6133:
6123:
6098:
6094:
6088:
6053:
6049:
6039:
6004:
6000:
5990:
5965:
5961:
5954:
5909:
5905:
5845:
5841:
5831:
5788:
5785:Gut Microbes
5784:
5773:
5733:(1): 14430.
5730:
5726:
5716:
5673:
5669:
5659:
5618:
5614:
5608:
5581:
5577:
5567:
5534:
5530:
5520:
5483:
5479:
5469:
5432:
5428:
5418:
5385:
5379:
5373:
5328:
5324:
5314:
5287:
5283:
5273:
5240:
5236:
5230:
5218:. Retrieved
5213:
5204:
5161:
5157:
5147:
5135:. Retrieved
5130:
5121:
5089:. Retrieved
5084:Butyric acid
5083:
5065:
5035:
5031:
5009:
4982:(1): 54–62.
4979:
4975:
4965:
4956:
4949:. Retrieved
4921:
4917:
4907:
4872:
4868:
4804:
4800:
4772:
4740:
4736:
4709:. Retrieved
4704:
4680:. Retrieved
4675:
4640:
4615:
4611:
4605:
4586:
4574:. Retrieved
4569:
4559:
4550:
4544:
4517:
4511:
4476:
4472:
4462:
4419:
4415:
4405:
4393:. Retrieved
4383:
4346:
4342:
4302:
4298:
4288:
4261:
4257:
4247:
4220:
4216:
4186:
4182:
4172:
4127:
4123:
4117:
4109:
4097:. Retrieved
4077:
4066:
4033:
4029:
4023:
4011:. Retrieved
4006:
3966:
3962:
3937:. Retrieved
3933:
3924:
3889:
3886:Gut Microbes
3885:
3838:(12): 1348.
3835:
3831:
3806:
3787:
3783:
3773:
3761:
3756:
3748:
3744:
3740:
3731:
3723:
3719:
3710:
3681:
3663:Butyric acid
3633:. Retrieved
3607:
3561:
3523:
3519:
3468:
3462:
3449:
3446:Butyric Acid
3426:
3409:blood plasma
3403:
3184:
3180:
3178:
3145:
3124:
3112:
3093:
3078:angiogenesis
3068:promoter in
3042:colon cancer
3023:
2996:
2992:Fas receptor
2930:
2908:
2877:
2869:
2865:
2853:
2849:C. difficile
2848:
2844:
2838:
2818:
2760:inflammation
2745:
2742:Biochemistry
2712:
2692:mitochondria
2685:
2669:
2629:
2566:
2519:
2422:Lower bound
2397:Lower bound
2384:Lower bound
2371:Lower bound
2358:Lower bound
2283:Pharmacology
2256:
2250:
2239:
2228:
2200:
2159:spring onion
2084:
2045:
2033:
2022:
2015:
2008:
2001:
1994:
1986:
1977:
1970:
1891:crotonyl CoA
1844:
1754:cleavage of
1749:
1744:
1737:
1730:
1723:
1716:
1709:
1702:
1679:
1654:
1631:
1628:butyric acid
1566:
1547:
1537:
1506:
1468:). It has a
1462:fermentation
1405:
1395:
1391:
1371:
1361:
1357:
1303:
1254:Butyric acid
1253:
1252:
1150:
1128:Autoignition
1063:
1019:
986:
964:
937:
910:
889:
854:
850:
846:
775:
733:
714:
682:
639:= 76 kJ/mol
636:
384:RTECS number
342:Butyric+acid
101:Identifiers
83:Other names
18:
8543:Fatty acids
8460:Ginkgotoxin
8428:Activators:
8325:Inhibitors:
8299:Activators:
8271:Inhibitors:
8230:Valinomycin
8182:Inhibitors:
8129:NNC 05-2090
8066:Inhibitors:
8044:Transporter
7885:Resminostat
7880:Quisinostat
7875:Pracinostat
7855:Niacinamide
7845:Martinostat
7770:Abexinostat
7554:Palmitoleic
7523:Arachidonic
7487:γ-Linolenic
7394:Myristoleic
7333:α-Parinaric
7327:Stearidonic
7321:α-Linolenic
7273:Decadienoic
7212:Ceroplastic
7176:Nonacosylic
7116:Nonadecylic
7004:fatty acids
6825:: 112–121.
6327:(5): 1026.
5791:(1): 1–11.
5452:2158/962790
3413:portal vein
3258:Butyryl-CoA
3026:homeostasis
3014:homeostasis
2895:(GPR109A),
2676:butyryl–CoA
2666:Metabolism
2632:colonocytes
2567:Like other
2465:Entry note
2309:Entry note
1904:butyryl CoA
1583:, which is
1552:ginkgo tree
1540:octyl ester
1442:breast milk
1165:median dose
1151:Lethal dose
1130:temperature
1117:Flash point
1014:Signal word
828:Space group
709:Henry's law
623:Sublimation
571:Appearance
520:Properties
262:100.003.212
194:ChEMBL14227
173:CHEBI:30772
8522:Categories
8421:Vigabatrin
8416:Valpromide
8385:lemon balm
8371:Phenelzine
8353:Gabaculine
8235:Vigabatrin
8200:Evans blue
8144:SKF-89976A
8104:Gabaculine
8079:Arecaidine
8036:modulators
8029:metabolism
7960:Valpromide
7925:Trapoxin B
7890:Romidepsin
7830:Givinostat
7820:Entinostat
7790:Belinostat
7164:Carboceric
7146:Lignoceric
7140:Tricosylic
7080:Tridecylic
7056:Pelargonic
6140:(5): 325.
5486:(1): 135.
5480:Microbiome
5137:1 February
4958:metabolism
4711:27 October
4099:11 October
3939:26 October
3635:27 October
3423:References
3289:Tributyrin
3127:vasculitic
3108:probiotics
2715:tributyrin
2672:XM-ligases
2269:stink bomb
2265:bitterling
2179:prebiotics
2072:celluloses
1752:glycolytic
1579:, forming
1563:Industrial
1558:Production
1488:, whereas
1431:plant oils
1427:animal fat
1415:hydrolysis
1402:Occurrence
1362:butanoates
1145:2.2–13.4%
998:Pictograms
957:combustion
819:Monoclinic
806:Structure
657:Solubility
625:conditions
559:Molar mass
410:40UIR9Q29H
293:IUPHAR/BPS
205:ChemSpider
138:3D model (
108:CAS Number
8358:Isoniazid
8220:Nigericin
8185:β-Alanine
8159:Tiagabine
8149:SNAP-5114
8074:β-Alanine
8033:transport
7977:See also:
7895:Scriptaid
7800:Capsaicin
7572:Paullinic
7517:Sciadonic
7499:Pinolenic
7279:Lauroleic
7194:Lacceroic
7122:Arachidic
7068:Undecylic
7020:Propionic
7012:Saturated
6654:1097-4172
6361:148568580
6321:Nutrients
5805:1949-0976
5551:0893-8512
5410:220337072
5178:1550-4131
5111:ignored (
5091:15 August
4938:0312-5963
4924:(1): 14.
4875:: 56–63.
4737:Nutrients
4705:BindingDB
4495:1528-0012
4438:1440-1746
3832:Nutrients
3572:CRC Press
3210:, is the
3185:butanoate
3169:addiction
3142:Addiction
3135:symbiosis
3074:apoptosis
3038:apoptosis
3032:(UC) and
2886:targets:
2832:activate
2822:dysbiosis
2723:dibutyrin
2708:autophagy
2662:(FATP4).
2654:(SMCT1),
2607:chromatin
2540:of human
2532:, so its
2444:1,032,000
2419:2,000,000
2394:2,000,000
2381:2,000,000
2368:2,000,000
2355:2,000,000
2211:anhydride
2197:Reactions
2155:radicchio
2135:asparagus
2127:Jerusalem
1934:phosphate
1896:crotonase
1847:succinate
1760:molecules
1685:anaerobic
1621:oxidation
1596:+ CO + CH
1511:of human
1454:body odor
1358:butyrates
1313:with the
1219:1-Butanol
989:labelling
930:formation
904:Std molar
821:(−43 °C)
791:Viscosity
651:Miscible
421:UN number
275:EC Number
8476:See also
8139:Riluzole
8119:Muscimol
8109:Guvacine
7840:Kevetrin
7810:Curcumin
7785:Apicidin
7675:Gadoleic
7656:Sapienic
7625:Nervonic
7560:Vaccenic
7493:Calendic
7471:Linoleic
7267:Decenoic
7261:Octenoic
7182:Melissic
7170:Montanic
7104:Margaric
7098:Palmitic
7086:Myristic
7050:Caprylic
7044:Enanthic
6947:28682229
6906:40791780
6898:28255755
6889:11107568
6849:25486626
6797:23643695
6752:21989194
6662:25036629
6588:18655767
6553:22517765
6504:18573671
6496:26224132
6461:19707587
6421:PLOS ONE
6402:15213223
6353:31067776
6299:24567795
6248:25545642
6199:26773933
6164:23526298
6115:25766751
6080:22517765
6031:21464244
5982:22194341
5938:24828484
5880:25343515
5823:33064972
5765:30258117
5708:24226773
5643:24226770
5600:29067994
5559:38421181
5512:30077182
5461:25435420
5402:32623619
5365:30356183
5306:31279007
5265:22633025
5257:24833634
5196:21531334
5062:23789956
5006:15717057
4951:18 March
4899:26868600
4833:25741338
4769:25875123
4648:Archived
4594:Archived
4503:25680668
4454:20666740
4446:20136989
4395:24 March
4375:27446020
4280:11157351
4239:14747692
4164:18218779
4058:23512190
4050:12523562
3985:21454438
3916:26963409
3864:29231905
3295:See also
3230:Examples
3181:butyrate
3066:Fas gene
2972:cytokine
2910:in vitro
2851:growth.
2752:diabetes
2603:histones
2564:(GPCR),
2558:-coupled
2509:Agonist
2215:chloride
2163:broccoli
2139:beetroot
2101:include
2080:ruminant
2052:oat bran
1980:-butanol
1959:butyrate
1953:to form
1791:hydrogen
1768:oxidized
1764:pyruvate
1688:bacteria
1682:obligate
1585:oxidised
1529:-coupled
1387:βούτῡρον
1300:βούτῡρον
1195:Related
1064:NFPA 704
980:Hazards
751:(χ)
711:constant
234:DrugBank
127:461-55-2
119:107-92-6
8533:Flavors
8210:Glycine
8099:EF-1502
7613:Gondoic
7603:Elaidic
7566:Rumenic
7529:Adrenic
7422:Punicic
7200:Psyllic
7158:Cerotic
7134:Behenic
7110:Stearic
7038:Caproic
7032:Valeric
7026:Butyric
6840:4293340
6788:3766384
6743:3272277
6703:1612357
6544:3378095
6452:2727000
6429:Bibcode
6344:6566851
6290:3926973
6239:4353849
6155:3631117
6071:3378095
6022:3101455
5929:4035769
5871:4817703
5850:Bibcode
5814:7575005
5756:6158259
5735:Bibcode
5699:3869884
5678:Bibcode
5651:4408815
5623:Bibcode
5503:6091101
5356:6296767
5333:Bibcode
5187:3099420
5053:4084603
4976:NeuroRx
4946:1717195
4890:4903954
4824:4332351
4760:4425176
4682:13 July
4620:Bibcode
4366:4923077
4349:: 979.
4321:1779073
4155:2542871
4132:Bibcode
4013:13 July
3907:4939913
3855:5748798
3528:Bibcode
3439::
3311:Histone
3070:T cells
2778:during
2756:obesity
2660:SLC27A4
2656:SLC27A1
2526:ionized
2488:3.8–4.9
2475:2.9–4.6
2432:511,000
2279:crews.
2277:whaling
2271:by the
2171:cabbage
2143:chicory
1973:acetone
1920:C=O−CoA
1758:to two
1756:glucose
1696:species
1573:propene
1544:parsnip
1478:Mammals
1396:buturum
1392:butyrum
1368:History
1294:; from
906:entropy
799:(15 °C)
795:1.814 c
730:Acidity
713: (
663:ethanol
590:Density
553:
351:PubChem
244:DB03568
8313:GABA-T
8249:Enzyme
8134:NO-711
8084:CI-966
7708:(20:1)
7702:(18:1)
7696:(16:1)
7677:(20:1)
7658:(16:1)
7639:(20:3)
7633:(20:2)
7627:(24:1)
7621:(22:1)
7619:Erucic
7615:(20:1)
7609:-18:1)
7599:(18:1)
7580:(20:3)
7574:(20:1)
7568:(18:2)
7562:(18:1)
7556:(16:1)
7537:(22:5)
7535:Osbond
7531:(22:4)
7525:(20:4)
7519:(20:3)
7513:(20:3)
7507:(20:2)
7501:(18:3)
7495:(18:3)
7489:(18:3)
7483:-18:2)
7473:(18:2)
7467:(18:1)
7461:(14:1)
7442:(20:4)
7436:(20:3)
7430:(18:3)
7424:(18:3)
7418:-18:3)
7408:(18:3)
7402:(16:1)
7396:(14:1)
7377:(24:6)
7371:(24:5)
7365:(22:6)
7359:(22:5)
7353:(20:5)
7347:(20:4)
7341:(20:3)
7335:(18:4)
7329:(18:4)
7323:(18:3)
7317:(16:4)
7311:(16:3)
7305:(14:3)
7299:(14:2)
7293:(14:1)
7287:(12:2)
7281:(12:1)
7275:(10:2)
7269:(10:1)
7206:Geddic
7074:Lauric
7062:Capric
7000:Lipids
6945:
6904:
6896:
6886:
6847:
6837:
6795:
6785:
6750:
6740:
6701:
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