3677:. Generally, the epidermal lipid matrix is composed of an equimolar mixture of ceramides (about 50% by weight), cholesterol (25%), and free fatty acids (15%). Saturated fatty acids 16 and 18 carbons in length are the dominant types in the epidermis, while unsaturated fatty acids and saturated fatty acids of various other lengths are also present. The relative abundance of the different fatty acids in the epidermis is dependent on the body site the skin is covering. There are also characteristic epidermal fatty acid alterations that occur in
413:
766:, with three double bonds, favors a hooked shape. The effect of this is that, in restricted environments, such as when fatty acids are part of a phospholipid in a lipid bilayer or triglycerides in lipid droplets, cis bonds limit the ability of fatty acids to be closely packed, and therefore can affect the melting temperature of the membrane or of the fat. Cis unsaturated fatty acids, however, increase cellular membrane fluidity, whereas trans unsaturated fatty acids do not.
1799:
290:
5392:
3370:, which involves replacement of a C-H bond with C-O bond. The process requires oxygen (air) and is accelerated by the presence of traces of metals, which serve as catalysts. Doubly unsaturated fatty acids are particularly prone to this reaction. Vegetable oils resist this process to a small degree because they contain antioxidants, such as
2626:
Malonyl-CoA is then involved in a repeating series of reactions that lengthens the growing fatty acid chain by two carbons at a time. Almost all natural fatty acids, therefore, have even numbers of carbon atoms. When synthesis is complete the free fatty acids are nearly always combined with glycerol
4750:
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
3912:
Note also that the "−" in the omega-notation is a minus sign, and "ω−3" should in principle be read "omega minus three". However, it is very common (especially in non-scientific literature) to write it "ω-3" (with a hyphen/dash) and read it as "omega-three". See for example Karen Dooley (2008),
2456:
are both 18:3, they may be unambiguously described as 18:3n3 and 18:3n6 fatty acids, respectively. For the same purpose, IUPAC recommends using a list of double bond positions in parentheses, appended to the C:D notation. For instance, IUPAC recommended notations for α- and γ-linolenic acid are
1902:
end. Thus, in an 18 carbon fatty acid, a double bond between C-12 (or ω−6) and C-13 (or ω−5) is said to be "at" position C-12 or ω−6. The IUPAC naming of the acid, such as "octadec-12-enoic acid" (or the more pronounceable variant "12-octadecanoic acid") is always based on the "C" numbering.
1746:
Most fatty acids are even-chained, e.g. stearic (C18) and oleic (C18), meaning they are composed of an even number of carbon atoms. Some fatty acids have odd numbers of carbon atoms; they are referred to as odd-chained fatty acids (OCFA). The most common OCFA are the saturated C15 and C17
4697:
Uptake of valproic acid was reduced in the presence of 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
4698:
acids. ... Based on these reports, valproic acid is thought to be transported bidirectionally between blood and brain across the BBB via two distinct mechanisms, monocarboxylic acid-sensitive and medium-chain fatty acid-sensitive transporters, for efflux and uptake, respectively.
3525:
or fatty acids for this purpose, but fatty acids release more energy per gram. Fatty acids (provided either by ingestion or by drawing on triglycerides stored in fatty tissues) are distributed to cells to serve as a fuel for muscular contraction and general metabolism.
3763:
Esters of fatty acids with simpler alcohols (such as methyl-, ethyl-, n-propyl-, isopropyl- and butyl esters) are used as emollients in cosmetics and other personal care products and as synthetic lubricants. Esters of fatty acids with more complex alcohols, such as
232:
of an even number of carbon atoms, from 4 to 28. Fatty acids are a major component of the lipids (up to 70% by weight) in some species such as microalgae but in some other organisms are not found in their standalone form, but instead exist as three main classes of
825:
The geometric differences between the various types of unsaturated fatty acids, as well as between saturated and unsaturated fatty acids, play an important role in biological processes, and in the construction of biological structures (such as cell membranes).
3540:
Fatty acids that are required for good health but cannot be made in sufficient quantity from other substrates, and therefore must be obtained from food, are called essential fatty acids. There are two series of essential fatty acids: one has a double bond
5279:
Aizpurua-Olaizola O, Ormazabal M, Vallejo A, Olivares M, Navarro P, Etxebarria N, et al. (January 2015). "Optimization of supercritical fluid consecutive extractions of fatty acids and polyphenols from Vitis vinifera grape wastes".
3322:. The hydrogenation of triglycerides (vs fatty acids) is advantageous because the carboxylic acids degrade the nickel catalysts, affording nickel soaps. During partial hydrogenation, unsaturated fatty acids can be isomerized from
185:
2674:. The levels of "free fatty acids" in the blood are limited by the availability of albumin binding sites. They can be taken up from the blood by all cells that have mitochondria (with the exception of the cells of the
3252:
of 4.96, being only slightly weaker than acetic acid (4.76). As the chain length increases, the solubility of the fatty acids in water decreases, so that the longer-chain fatty acids have minimal effect on the
2754:
increasingly cold environments lead to increasingly high cell membrane content of both monounsaturated and polyunsaturated fatty acids, to maintain greater membrane fluidity (and functionality) at the lower
2702:. These cells have to manufacture their own fatty acids from carbohydrates, as described above, in order to produce and maintain the phospholipids of their cell membranes, and those of their organelles.
3883:(also ω−x or omega-x) nomenclature a double bond of the fatty acid is located on the xth carbon–carbon bond, counting from the terminal methyl carbon (designated as n or ω) toward the carbonyl carbon.
742:
configuration means that the two hydrogen atoms adjacent to the double bond stick out on the same side of the chain. The rigidity of the double bond freezes its conformation and, in the case of the
6207:
3901:
For double bonds, these two mistakes happen to compensate each other; so that a "ω−3" fatty acid indeed has the double bond between the 3rd and 4th carbons from the end, counting the methyl as 1.
1933:
In the context of human diet and fat metabolism, unsaturated fatty acids are often classified by the position of the double bond closest between to the ω carbon (only), even in the case of
3549:
away from the methyl end. Humans lack the ability to introduce double bonds in fatty acids beyond carbons 9 and 10, as counted from the carboxylic acid side. Two essential fatty acids are
5315:
Breuer, B.; Stuhlfauth, T.; Fock, H. P. (1987). "Separation of Fatty Acids or Methyl Esters
Including Positional and Geometric Isomers by Alumina Argentation Thin-Layer Chromatography".
3728:
with bonded phenylsulfonic acid groups whose hydrogen atoms have been exchanged for silver ions). The role of silver lies in its ability to form complexes with unsaturated compounds.
4567:
1883:), which is the last letter in the Greek alphabet. A third numbering convention counts the carbons from that end, using the labels "ω", "ω−1", "ω−2". Alternatively, the label "ω−
2746:), resulting in cell membranes that are more costly to maintain. This maintenance cost has been argued to be one of the key causes for the high metabolic rates and concomitant
6200:
5001:
4455:
2106:
2152:- notation, where appropriate. This notation is generally more verbose than common nomenclature, but has the advantage of being more technically clear and descriptive.
2432:
is an 18:3 fatty acid and its three double bonds are located at positions Δ, Δ, and Δ. This notation can be ambiguous, as some different fatty acids can have the same
1755:
respectively, which are found in dairy products. On a molecular level, OCFAs are biosynthesized and metabolized slightly differently from the even-chained relatives.
2074:) are non-systematic historical names, which are the most frequent naming system used in literature. Most common fatty acids have trivial names in addition to their
3306:
pressure, 150 °C, and nickel supported on silica as a catalyst. This treatment affords saturated fatty acids. The extent of hydrogenation is indicated by the
2223:-Δ octadecadienoic acid". This nomenclature has the advantage of being less verbose than systematic nomenclature, but is no more technically clear or descriptive.
6193:
3870:
Each double bond in the fatty acid is indicated by Δx, where the double bond is located on the xth carbon–carbon bond, counting from the carboxylic acid end.
5361:
3903:
However, for substitutions and other purposes, they don't: a hydroxyl "at ω−3" is on carbon 15 (4th from the end), not 16. See for example this article.
3479:
up to a location near the heart (where the arteries and veins are larger). The thoracic duct empties the chylomicrons into the bloodstream via the left
2294:
both provides names for individual compounds and classifies them by their likely biosynthetic properties in animals. A double bond is located on the
3276:
as an indicator. This analysis is used to determine the free fatty acid content of fats; i.e., the proportion of the triglycerides that have been
2113:
3721:
5458:
5045:
4598:
4508:
4349:
4122:
4097:
3352:
certain unsaturated fatty acids are cleaved in molten alkali, a reaction which was, at one point of time, relevant to structure elucidation.
315:
Fatty acids are classified in many ways: by length, by saturation vs unsaturation, by even vs odd carbon content, and by linear vs branched.
5065:; Wood, JodiAnne T.; Mann, J. Douglas; Faurot, Keturah R.; MacIntosh, Beth A.; Majchrzak-Hong, Sharon F.; Gross, Jacklyn R. (August 2015).
2690:
and water. Cells in the central nervous system, although they possess mitochondria, cannot take free fatty acids up from the blood, as the
2734:. Studies on bird fatty acid composition have noted similar proportions to mammals but with 1/3rd less omega-3 fatty acids as compared to
3557:(ALA). These fatty acids are widely distributed in plant oils. The human body has a limited ability to convert ALA into the longer-chain
2738:
for a given body size. This fatty acid composition results in a more fluid cell membrane but also one that is permeable to various ions (
1837:
The position of each carbon atom in the backbone of a fatty acid is usually indicated by counting from 1 at the −COOH end. Carbon number
782:
sides of the chain. As a result, they do not cause the chain to bend much, and their shape is similar to straight saturated fatty acids.
746:
isomer, causes the chain to bend and restricts the conformational freedom of the fatty acid. The more double bonds the chain has in the
225:
189:
5018:
4472:
2750:
of mammals and birds. However polyunsaturation of cell membranes may also occur in response to chronic cold temperatures as well. In
4809:
Hulbert AJ, Faulks S, Buttemer WA, Else PL (November 2002). "Acyl composition of muscle membranes varies with body size in birds".
3780:
are consumed in food, or used for personal care and water treatment, or used as synthetic lubricants or fluids for metal working.
4378:
2631:, the main storage form of fatty acids, and thus of energy in animals. However, fatty acids are also important components of the
3607:
Blood fatty acids adopt distinct forms in different stages in the blood circulation. They are taken in through the intestine in
1879:
Although fatty acids can be of diverse lengths, in this second convention the last carbon in the chain is always labelled as ω (
5224:"Biogeographic and disease-specific alterations in epidermal lipid composition and single-cell analysis of acral keratinocytes"
3813:
709:
3899:
Another common mistake is to say that the position of a bond in omega-notation is the number of the carbon closest to the END.
5842:
4944:
3483:. At this point the chylomicrons can transport the triglycerides to tissues where they are stored or metabolized for energy.
171:
5836:
4885:
Raynard RS, Cossins AR (May 1991). "Homeoviscous adaptation and thermal compensation of sodium pump of trout erythrocytes".
4453:
Anneken, David J.; Both, Sabine; Christoph, Ralf; Fieg, Georg; Steinberner, Udo; Westfechtel, Alfred (2006). "Fatty Acids".
4064:
3318:
than the unsaturated precursors, the process is called hardening. Related technology is used to convert vegetable oils into
5423:
4974:
3448:
are not directly released into the intestinal capillaries. Instead they are absorbed into the fatty walls of the intestine
6362:
5407:
3808:
2409:
is the number of double bonds in the fatty acid. If D is more than one, the double bonds are assumed to be interrupted by
371:
5067:"Diet-induced changes in n-3 and n-6 derived endocannabinoids and reductions in headache pain and psychological distress"
2583:
as the first important step in the conversion of carbohydrates into fatty acids. Pyruvate is then decarboxylated to form
6352:
3612:
1954:
5782:
6357:
5431:
4614:
Zechner, R.; Strauss, J. G.; Haemmerle, G.; Lass, A.; Zimmermann, R. (2005). "Lipolysis: pathway under construction".
814:(such as cattle and sheep). They are produced, by fermentation, in the rumen of these animals. They are also found in
352:
5907:
2486:, fatty acids are known as non-esterified fatty acids (NEFAs) or free fatty acids (FFAs). FFAs are always bound to a
6322:
5978:
5895:
5776:
5770:
3980:
Chen, Lin (2012). "Biodiesel production from algae oil high in free fatty acids by two-step catalytic conversion".
3717:
3659:
3232:
2666:
The "uncombined fatty acids" or "free fatty acids" found in the circulation of animals come from the breakdown (or
1934:
1823:
229:
5806:
2670:) of stored triglycerides. Because they are insoluble in water, these fatty acids are transported bound to plasma
6045:
5901:
5451:
3514:
3390:
Unsaturated fatty acids are susceptible to degradation by ozone. This reaction is practiced in the production of
1772:
343:
270:
5764:
1953:(18-carbon, Δ), and arachidonic acid (20-carbon, Δ) are all classified as "ω−6" fatty acids; meaning that their
3818:
3655:
3437:
5350:
2691:
294:
6098:
4527:
Ferre, P.; Foufelle, F. (2007). "SREBP-1c
Transcription Factor and Lipid Homeostasis: Clinical Perspective".
3853:"C:D" is the numerical symbol: total amount of (C)arbon atoms of the fatty acid, and the number of (D)ouble (
2722:
discovered that mammalian cell membranes are composed of a higher proportion of polyunsaturated fatty acids (
5752:
5703:
5697:
5691:
3701:
step that breaks down their original esters (triglycerides, waxes, phospholipids etc.) and converts them to
3616:
2699:
1764:
324:
145:
5758:
3752:, which are precursors to surfactants, detergents, and lubricants. Other applications include their use as
2078:(see below). These names frequently do not follow any pattern, but they are concise and often unambiguous.
6219:
5972:
5932:
5926:
5867:
5740:
5062:
3518:
3445:
3433:
2695:
2675:
2616:
6161:
6153:
6134:
6115:
5709:
2321:
fatty acid, and so it is likely to share a biosynthetic pathway with other compounds of this type. The ω−
342:
Medium-chain fatty acids (MCFAs) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form
6002:
5996:
5853:
5824:
5818:
5812:
5685:
4561:
3710:
3562:
3492:
2656:
2636:
874:
6173:
5879:
5873:
5746:
3257:
of an aqueous solution. Near neutral pH, fatty acids exist at their conjugate bases, i.e. oleate, etc.
2595:
where the synthesis of fatty acids occurs. This cannot occur directly. To obtain cytosolic acetyl-CoA,
3914:
6347:
5954:
5830:
5734:
5728:
5655:
5444:
4775:
4659:"Small molecular drug transfer across the blood–brain barrier via carrier-mediated transport systems"
3989:
3798:
3566:
3535:
3349:
2723:
2555:
2453:
2025:
1946:
1938:
1793:
1038:
193:
84:
412:
5800:
5788:
3793:
3777:
3698:
3554:
2449:
2429:
2385:
2369:
2365:
2341:
notation in technical documents. The most commonly researched fatty acid biosynthetic pathways are
2307:
2207:
2201:
2130:
1930:
is Δ, meaning that it has double bonds between carbons 5 and 6, 8 and 9, 11 and 12, and 14 and 15.
967:
763:
720:
62:
57:
6080:
6056:
6013:
5918:
5720:
5197:
5122:
4910:
4639:
4313:
3956:
3828:
3706:
3570:
3558:
3546:
3542:
3475:, which merges into larger lymphatic vessels. It is transported via the lymphatic system and the
2735:
2727:
2475:
2349:
2342:
2330:
2311:
2251:
2243:
1752:
1748:
1519:
1466:
1413:
1353:
1289:
1225:
1132:
1028:
957:
795:
791:
787:
164:
105:
100:
95:
90:
4590:
4583:
2440:
numbers. Consequently, when ambiguity exists this notation is usually paired with either a Δ or
798:) carbon atoms after it, and all double bonds have a cis configuration. Most fatty acids in the
3231:
Fatty acids do not show a great variation in their acidities, as indicated by their respective
6167:
5944:
5619:
5595:
5559:
5332:
5297:
5261:
5243:
5189:
5181:
5104:
5086:
5041:
5035:
5014:
4902:
4867:
4826:
4791:
4741:
4688:
4631:
4594:
4546:
4504:
4468:
4355:
4345:
4305:
4264:
4194:
4118:
4093:
4005:
3773:
3682:
3638:, is distinctive and enables animals with a keen sense of smell to differentiate individuals.
3602:
3517:), reactions with oxygen release a lot of energy, captured in the form of large quantities of
3510:
3449:
2683:
2608:
2604:
2487:
1798:
246:
133:
2607:
and carried across the inner mitochondrial membrane into the cytosol. There it is cleaved by
6021:
5990:
5861:
5794:
5679:
5643:
5583:
5324:
5289:
5251:
5235:
5171:
5094:
5078:
5006:
4894:
4857:
4818:
4783:
4731:
4723:
4678:
4670:
4623:
4536:
4460:
4387:
4295:
4254:
4246:
4184:
4174:
3997:
3946:
3904:
3858:
3857:) bonds in it; if D > 1 it is assumed that the double bonds are separated by one or more
3624:
3269:
2600:
2410:
2196:
2122:
2117:, published in 1979, along with a recommendation published specifically for lipids in 1977.
2060:
1927:
1906:
The notation Δ is traditionally used to specify a fatty acid with double bonds at positions
1587:
1536:
1299:
1149:
402:
250:
4024:
3302:
of unsaturated fatty acids is widely practiced. Typical conditions involve 2.0–3.0 MPa of H
1898:
in a fatty acid chain is always specified by giving the label of the carbon closest to the
5631:
5613:
5607:
5547:
5523:
4215:
4157:
Beermann, C.; Jelinek, J.; Reinecker, T.; Hauenschild, A.; Boehm, G.; Klör, H.-U. (2003).
3769:
3647:
3480:
3361:
3311:
3273:
2971:
2660:
2502:
2100:
2029:
703:
646:
217:
52:
4433:
Sudan
University of Science & Technology SUST Journal of Natural and Medical Sciences
5397:
4779:
4139:
4047:
3993:
349:
Long-chain fatty acids (LCFAs) are fatty acids with aliphatic tails of 13 to 21 carbons.
6317:
6296:
6039:
5984:
5966:
5661:
5589:
5535:
5487:
5256:
5223:
5099:
5066:
4736:
4711:
4627:
4392:
4373:
4259:
4234:
4025:"Sur plusieurs corps gras, et particulièrement sur leurs combinaisons avec les alcalis"
3803:
3590:
3506:
3367:
3284:
3220:
3037:
3015:
2679:
2611:
into acetyl-CoA and oxaloacetate. The oxaloacetate is returned to the mitochondrion as
2565:
1919:
1915:
1861:
1827:
596:
416:
254:
5222:
Merleev, Alexander A.; Le, Stephanie T.; Alexanian, Claire; et al. (2022-08-22).
5176:
5159:
4683:
4658:
4189:
4163:−3 long-chain polyunsaturated fatty acids on the fat metabolism of healthy volunteers"
4158:
3440:
are absorbed directly into the blood via intestine capillaries and travel through the
289:
6341:
6301:
6291:
6286:
6185:
6142:
6123:
6092:
6027:
5960:
5938:
5649:
5637:
5571:
5565:
5553:
5517:
5511:
5479:
5201:
4766:
Hulbert AJ, Else PL (August 1999). "Membranes as possible pacemakers of metabolism".
4428:
3908:
3823:
3745:
3741:
3630:
It is proposed that the blend of fatty acids exuded by mammalian skin, together with
3550:
3476:
3338:
3315:
3307:
3299:
3288:
3242:
3147:
3125:
2711:
2652:
2588:
2569:
2543:
2212:
2211:- prefix, indicating the configuration of the molecule around the bond. For example,
2160:
1942:
1776:
1689:
1638:
1235:
815:
807:
759:
546:
521:
446:
365:
157:
47:
4914:
4898:
4643:
4429:"Chemical Reactions Taken Place During deep-fat Frying and Their Products: A review"
4317:
3960:
17:
6070:
6033:
5889:
5667:
5625:
5601:
5577:
5505:
5499:
5493:
4216:"IUPAC Lipid nomenclature: Appendix A: names of and symbols for higher fatty acids"
4001:
3686:
3635:
3574:
3502:
3453:
3391:
2949:
2747:
2648:
2632:
2628:
2576:
2539:
2535:
2527:
2498:
2479:
2303:
2148:
2142:
2066:
1831:
1423:
671:
621:
571:
394:
336:
300:
242:
238:
209:
112:
4948:
4464:
4113:
Cifuentes, Alejandro, ed. (2013-03-18). "Microbial
Metabolites in the Human Gut".
754:
bonds, it becomes quite curved in its most accessible conformations. For example,
4978:
4727:
4087:
4072:
786:
In most naturally occurring unsaturated fatty acids, each double bond has three (
6238:
6086:
5673:
5541:
5529:
5328:
5082:
4300:
4283:
3749:
3674:
3666:
3631:
3608:
3582:
3578:
3461:
3457:
3441:
3379:
3059:
2927:
2772:
2756:
2620:
2596:
2469:
2126:
1895:
1476:
819:
716:
496:
471:
117:
5239:
4427:
Mariod, Abdalbasit; Omer, Nuha; Al, El Mugdad; Mokhtar, Mohammed (2014-09-09).
6269:
6259:
6233:
6064:
3725:
3662:
3620:
3586:
3411:
3371:
3277:
2584:
2580:
2523:
2090:
2086:
2021:
1768:
1370:
778:
configuration, by contrast, means that the adjacent two hydrogen atoms lie on
755:
308:
5247:
5185:
5090:
5010:
3744:, as lubricants. Fatty acids are also converted, via their methyl esters, to
3219:
Fatty acids exhibit reactions like other carboxylic acids, i.e. they undergo
2040:
The following table describes the most common systems of naming fatty acids.
6104:
5293:
4822:
3951:
3678:
3651:
3468:
3428:
3375:
3319:
3265:
3081:
2768:
2667:
2644:
2640:
2506:
803:
328:
221:
205:
138:
5301:
5265:
5193:
5108:
4871:
4830:
4795:
4787:
4745:
4692:
4674:
4635:
4550:
4359:
4268:
4235:"Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids"
4198:
4179:
4009:
2560:
In animals, fatty acids are formed from carbohydrates predominantly in the
1891:", where the "n" is meant to represent the number of carbons in the chain.
5336:
4906:
4309:
4284:"The Animal Fatty Acid Synthase: One Gene, One Polypeptide, Seven Enzymes"
4250:
4115:
Foodomics: Advanced Mass
Spectrometry in Modern Food Science and Nutrition
2187:, each double bond is indicated by Δ, where the double bond begins at the
6254:
4413:
4341:
3765:
3757:
3753:
3670:
3169:
3103:
2993:
2830:
2542:
represent another source. Some fatty acids are produced synthetically by
2531:
811:
3934:
3697:
The chemical analysis of fatty acids in lipids typically begins with an
806:) are not found in nature and are the result of human processing (e.g.,
377:
Saturated fatty acids have no C=C double bonds. They have the formula CH
4503:(4th ed.). New York: W. H. Freeman and Company. pp. 603–628.
3522:
3472:
3261:
2731:
2719:
2671:
2592:
2491:
2329:, or "omega" notation is common in popular nutritional literature, but
2318:
1818:
configuration are actually "kinked" rather than straight as shown here.
810:). Some trans fatty acids also occur naturally in the milk and meat of
5436:
4862:
4845:
4541:
3705:
esters, which are then separated by gas chromatography or analyzed by
184:
6278:
3945:(8–9). International Union of Pure and Applied Chemistry: 1307–1375.
3702:
3619:(LDL) after processing in the liver. In addition, when released from
3191:
2896:
2874:
2715:
2612:
2501:
food oils and fats by hydrolysis, contributing to the characteristic
1810:" labels are in red. The Greek letter labels are in green. Note that
332:
4712:"Role of monocarboxylate transporters in drug delivery to the brain"
3341:. Fatty alcohols are, however, more easily produced from fatty acid
2678:). Fatty acids can only be broken down in mitochondria, by means of
355:(VLCFAs) are fatty acids with aliphatic tails of 22 or more carbons.
253:
sources of fuel for animals and important structural components for
5467:
4928:
McCann; Widdowson; Food
Standards Agency (1991). "Fats and Oils".
3673:, free fatty acids form a water-impermeable barrier that prevents
3342:
2561:
2483:
2299:
2192:
2118:
1880:
1869:
1854:
1797:
750:
configuration, the less flexibility it has. When a chain has many
288:
234:
183:
2028:, whereas the rest are even-chain fatty acids. The difference is
5418:
3737:
2852:
2751:
2639:
out of which all the membranes of the cell are constructed (the
2428:, at intervals of 3 carbon atoms along the chain. For instance,
2199:
end of the molecule backbone. Each double bond is preceded by a
1873:
1853:= 1, 2, 3, etc. This is the numbering scheme recommended by the
406:
38:
6189:
5440:
4089:
Dictionnaire de chimie: Une approche étymologique et historique
34:
4159:"Short term effects of dietary medium-chain fatty acids and
3333:
More forcing hydrogenation, i.e. using higher pressures of H
2623:, the first committed step in the synthesis of fatty acids.
4581:
Voet, Donald; Voet, Judith G.; Pratt, Charlotte W. (2006).
3254:
188:
Three-dimensional representations of several fatty acids.
4049:
Recherches chimiques sur les corps gras d'origine animale
3897:
A common mistake is to say that the last carbon is "ω−1".
3569:(DHA), which can also be obtained from fish. Omega-3 and
3467:
From within the cell, the chylomicron is released into a
2470:
Deep frying § Oil deterioration and chemical changes
5425:
Prostaglandins, Leukotrienes & Essential Fatty Acids
4975:"USDA National Nutrient Database for Standard Reference"
2591:. However, this acetyl CoA needs to be transported into
1794:
Essential fatty acid § Nomenclature and terminology
249:. In any of these forms, fatty acids are both important
4407:
5034:
Bolsover, Stephen R.; et al. (15 February 2004).
4448:
4446:
4444:
4442:
3545:
away from the methyl end; the other has a double bond
2627:(three fatty acids to one glycerol molecule) to form
2522:
Fatty acids are usually produced industrially by the
2114:
762:, with two double bonds, has a more pronounced bend.
192:
fatty acids have perfectly straight chain structure.
4331:
4329:
4327:
4035:. Paris: H. Perronneau: 225–261 – via Gallica.
3933:
Moss, G. P.; Smith, P. A. S.; Tavernier, D. (1997).
3460:
and protein (protein coat) into a compound called a
2405:
is the number of carbon atoms in the fatty acid and
1802:
Numbering of carbon atoms. The systematic (IUPAC) C-
758:, with one double bond, has a "kink" in it, whereas
6310:
6277:
6268:
6247:
6226:
6152:
6133:
6114:
6055:
6012:
5917:
5852:
5719:
5478:
4374:"The Nomenclature of Lipids. Recommendations, 1976"
3337:and higher temperatures, converts fatty acids into
4582:
2694:is impervious to most free fatty acids, excluding
4999:Schumann, Klaus; Siekmann, Kurt (2000). "Soaps".
4566:: CS1 maint: DOI inactive as of September 2024 (
4499:Stryer, Lubert (1995). "Fatty acid metabolism.".
3740:, both for cosmetic purposes and, in the case of
3736:Fatty acids are mainly used in the production of
3718:silver ion complemented thin-layer chromatography
3716:Separation of unsaturated isomers is possible by
3366:Unsaturated fatty acids and their esters undergo
3310:. Hydrogenated fatty acids are less prone toward
2599:(produced by the condensation of acetyl-CoA with
818:from milk of ruminants, and may be also found in
4977:. U.S. Department of Agriculture. Archived from
4140:"Medium-Chain Acyl-CoA Dehydrogenase Deficiency"
5123:"Electronic Nose Created To Detect Skin Vapors"
4555:this process is outlined graphically in page 73
4052:. Paris: Levrault – via Internet Archive.
273:, though he initially used some variant terms:
228:. Most naturally occurring fatty acids have an
5002:Ullmann's Encyclopedia of Industrial Chemistry
4945:"More Than You Wanted To Know About Fats/Oils"
4589:(2nd ed.). John Wiley and Sons. pp.
4456:Ullmann's Encyclopedia of Industrial Chemistry
3444:just as other absorbed nutrients do. However,
3287:(soap-making), is a widely practiced route to
2615:. The cytosolic acetyl-CoA is carboxylated by
2457:18:3(9,12,15) and 18:3(6,9,12), respectively.
1926:ouble bond). Thus, for example, the 20-carbon
1894:In either numbering scheme, the position of a
401: = 16), which when neutralized with
6201:
5452:
5160:"Skin lipids in health and disease: A review"
4210:
4208:
3893:
3891:
3889:
1822:Most naturally occurring fatty acids have an
715:Unsaturated fatty acids have one or more C=C
165:
8:
1864:in sequence, starting with the first carbon
1811:
1767:, with no additional carbon atoms bonded as
822:of women who obtained them from their diet.
197:
196:ones are typically bent, unless they have a
5351:"Fatty Acids: Building Blocks for Industry"
4761:
4759:
3283:Neutralization of fatty acids, one form of
2306:end of the molecule backbone. For example,
6274:
6208:
6194:
6186:
5459:
5445:
5437:
3935:"IUPAC Compendium of Chemical Terminology"
2767:The following table gives the fatty acid,
172:
158:
29:
5255:
5175:
5098:
4861:
4735:
4682:
4540:
4494:
4492:
4490:
4488:
4486:
4484:
4391:
4299:
4258:
4188:
4178:
3950:
2775:composition of some common dietary fats.
2643:, and the membranes that enclose all the
5158:Knox, Sophie; O'Boyle, Niamh M. (2021).
5061:Ramsden, Christopher E.; Zamora, Daisy;
5040:. John Wiley & Sons. pp. 42ff.
4947:. Sundance Natural Foods. Archived from
4522:
4520:
4409:Dorland's Illustrated Medical Dictionary
4233:Pfeuffer, Maria; Jaudszus, Anke (2016).
4065:"Chronological history of lipid science"
2777:
2042:
1806:numbers are in blue. The omega-minus "ω−
828:
422:
411:
4969:
4967:
4965:
3925:
3841:
3374:. Fats and oils often are treated with
1860:Another convention uses letters of the
719:. The C=C double bonds can give either
393:. An important saturated fatty acid is
125:
72:
32:
4559:
3849:
3847:
3845:
3756:, texturizing agents, wetting agents,
3722:high-performance liquid chromatography
3720:. Other separation techniques include
3314:. Since the saturated fatty acids are
2682:followed by further combustion in the
2505:odor. An analogous process happens in
5217:
5215:
5213:
5211:
5153:
5151:
5149:
5147:
5145:
5143:
3665:within a lipid matrix. Together with
1914:,.... (The capital Greek letter "Δ" (
7:
4336:Rigaudy, J.; Klesney, S. P. (1979).
3915:Omega-three fatty acids and diabetes
3623:, fatty acids exist in the blood as
3456:. The triglycerides are coated with
830:Examples of Unsaturated Fatty Acids
4850:The Journal of Experimental Biology
4846:"Life, death and membrane bilayers"
4811:The Journal of Experimental Biology
2482:(plasma fatty acids), not in their
1868:the carboxyl group. Thus carbon α (
708:For a more comprehensive list, see
370:For a more comprehensive list, see
5843:6,9,12,15,18,21-Tetracosahexaenoic
5317:Journal of Chromatographic Science
4887:The American Journal of Physiology
4628:10.1097/01.mol.0000169354.20395.1c
4393:10.1111/j.1432-1033.1977.tb11778.x
4063:Leray, Claude (11 November 2017).
424:Examples of saturated fatty acids
25:
5837:9,12,15,18,21-Tetracosapentaenoic
5177:10.1016/j.chemphyslip.2021.105055
4338:Nomenclature of Organic Chemistry
3521:. Many cell types can use either
3497:Fatty acids are broken down to CO
2575:Carbohydrates are converted into
1779:bonded to the hydrocarbon chain.
5390:
4379:European Journal of Biochemistry
3724:(with short columns packed with
3501:and water by the intra-cellular
2706:Variation between animal species
1742:Even- vs odd-chained fatty acids
5367:from the original on 2018-04-23
5360:. American Cleaning Institute.
5164:Chemistry and Physics of Lipids
4899:10.1152/ajpregu.1991.260.5.R916
4117:. John Wiley & Sons, 2013.
3814:List of unsaturated fatty acids
3382:to remove the metal catalysts.
1771:to the main hydrocarbon chain.
710:List of unsaturated fatty acids
4768:Journal of Theoretical Biology
4002:10.1016/j.biortech.2012.02.033
3429:Digestion § Fat digestion
2647:within the cells, such as the
2333:has deprecated it in favor of
2125:end of the molecule backbone.
281:("acid fat" and "oily acid").
1:
4932:. Royal Society of Chemistry.
4465:10.1002/14356007.a10_245.pub2
3809:List of saturated fatty acids
3650:– the outermost layer of the
3613:very low density lipoproteins
2509:with risk of part corrosion.
2448:term. For instance, although
372:List of saturated fatty acids
327:(SCFAs) are fatty acids with
5037:Cell Biology: A Short Course
4728:10.2174/13816128113199990462
4585:Fundamentals of Biochemistry
4435:. Supplementary issue: 1–17.
4167:Lipids in Health and Disease
4138:Roth, Karl S. (2013-12-19).
3909:10.1016/0005-2760(75)90089-2
3654:– is composed of terminally
3356:Auto-oxidation and rancidity
3260:Solutions of fatty acids in
2815:
2812:
2809:
2806:
2803:
1763:Most common fatty acids are
269:) was introduced in 1813 by
5083:10.1016/j.jpain.2015.04.007
4710:Vijay N, Morris ME (2014).
4301:10.1096/fasebj.8.15.8001737
3295:Hydrogenation and hardening
3207:
3204:
3201:
3198:
3195:
3185:
3182:
3179:
3176:
3173:
3163:
3160:
3157:
3154:
3151:
3141:
3138:
3135:
3132:
3129:
3119:
3116:
3113:
3110:
3107:
3097:
3094:
3091:
3088:
3085:
3075:
3072:
3069:
3066:
3063:
3053:
3050:
3047:
3044:
3041:
3031:
3028:
3025:
3022:
3019:
3009:
3006:
3003:
3000:
2997:
2987:
2984:
2981:
2978:
2975:
2965:
2962:
2959:
2956:
2953:
2943:
2940:
2937:
2934:
2931:
2912:
2909:
2906:
2903:
2900:
2890:
2887:
2884:
2881:
2878:
2868:
2865:
2862:
2859:
2856:
2846:
2843:
2840:
2837:
2834:
2763:Fatty acids in dietary fats
2111:) derive from the standard
2030:relevant to gluconeogenesis
2024:of carbon atoms are called
405:is the most common form of
353:Very long chain fatty acids
265:The concept of fatty acid (
6379:
6323:Very long chain fatty acid
5240:10.1172/jci.insight.159762
3939:Pure and Applied Chemistry
3600:
3533:
3490:
3452:and reassemble again into
3426:
3359:
2553:
2467:
2087:cis-9-octadec-9-enoic acid
1830:(–COOH) at one end, and a
1791:
1773:Branched-chain fatty acids
707:
701:
369:
363:
344:medium-chain triglycerides
5329:10.1093/chromsci/25.7.302
3760:, or stabilizing agents.
3515:oxidative phosphorylation
3223:and acid-base reactions.
2917:
2820:
1834:(–CH3) at the other end.
1528:
1362:
1141:
866:
5896:7,10,13-Octadecatrienoic
5011:10.1002/14356007.a24_247
4930:The Composition of Foods
4844:Hulbert AJ (July 2003).
4086:Menten, P., ed. (2013).
4046:Chevreul, M. E. (1823).
4023:Chevreul, M. E. (1813).
3819:List of carboxylic acids
3617:low density lipoproteins
3438:medium-chain fatty acids
3215:Reactions of fatty acids
2700:medium-chain fatty acids
1876:) is C-3, and so forth.
1826:of carbon atoms, with a
1765:straight-chain compounds
419:, a saturated fatty acid
226:saturated or unsaturated
6220:metabolic intermediates
5294:10.1111/1750-3841.12715
5282:Journal of Food Science
5063:Makriyannis, Alexandros
5005:. Weinheim: Wiley-VCH.
4823:10.1242/jeb.205.22.3561
4545:(inactive 2024-09-11).
4459:. Weinheim: Wiley-VCH.
4092:. Bruxelles: De Boeck.
3952:10.1351/pac199567081307
3687:inflammatory conditions
2696:short-chain fatty acids
2191:th carbon–carbon bond,
2168:-Δ octadecadienoic acid
1841:is often abbreviated C-
1812:unsaturated fatty acids
698:Unsaturated fatty acids
331:tails of five or fewer
325:Short-chain fatty acids
224:chain, which is either
146:Fat interesterification
6046:7,10,13-Eicosatrienoic
5902:9,12,15-Eicosatrienoic
4788:10.1006/jtbi.1999.0955
4675:10.1602/neurorx.2.1.54
4180:10.1186/1476-511X-2-10
3982:Bioresource Technology
3675:evaporative water loss
3446:long-chain fatty acids
3245:, for example, has a p
2676:central nervous system
2617:acetyl-CoA carboxylase
2603:) is removed from the
2530:, with the removal of
2095:)-octadec-9-enoic acid
1819:
1129:22:6(4,7,10,13,16,19)
420:
312:
271:Michel Eugène Chevreul
201:
4251:10.3945/an.115.011387
4239:Advances in Nutrition
3711:infrared spectroscopy
3563:eicosapentaenoic acid
3530:Essential fatty acids
3513:. In the final step (
3493:Fatty acid metabolism
2657:endoplasmic reticulum
2637:phospholipid bilayers
2119:Carbon atom numbering
2036:Naming of fatty acids
2026:odd-chain fatty acids
1939:essential fatty acids
1935:multiple double bonds
1801:
1788:Carbon atom numbering
875:Eicosapentaenoic acid
415:
360:Saturated fatty acids
319:Length of fatty acids
292:
187:
6363:Edible oil chemistry
3799:Fatty acid synthesis
3611:, but also exist in
3567:docosahexaenoic acid
3555:alpha-linolenic acid
3536:Essential fatty acid
3423:Digestion and intake
3350:Varrentrapp reaction
2556:Fatty acid synthesis
2497:FFAs also form from
2298:carbon–carbon bond,
2020:Fatty acids with an
1872:) is C-2, carbon β (
1775:contain one or more
1039:Docosahexaenoic acid
389:COOH, for different
285:Types of fatty acids
85:Essential fatty acid
18:Saturated fatty acid
6353:Commodity chemicals
5071:The Journal of Pain
4893:(5 Pt 2): R916–24.
4780:1999JThBi.199..257H
4616:Curr. Opin. Lipidol
4220:www.sbcs.qmul.ac.uk
3994:2012BiTec.111..208C
3794:Fatty acid synthase
3778:polyethylene glycol
3699:interesterification
3559:omega-3 fatty acids
3471:capillary called a
3192:Canola/Rapeseed oil
2779:
2692:blood–brain barrier
2310:is classified as a
1530:Omega-5, 7, and 10:
954:20:5(5,8,11,14,17)
831:
425:
63:Polyunsaturated fat
58:Monounsaturated fat
6358:E-number additives
6099:8,11-Eicosadienoic
5979:Dihomo-γ-linolenic
5908:β-Eicosatetraenoic
5807:Dihomo-α-linolenic
5692:Heptatriacontanoic
5432:Fatty blood acids
4856:(Pt 14): 2303–11.
4386:(1): 11–21. 1977.
4282:Smith, S. (1994).
3829:Lactobacillic acid
3707:gas chromatography
3543:three carbon atoms
2778:
2728:omega-3 fatty acid
2572:during lactation.
2544:hydrocarboxylation
2129:are labelled with
1820:
1753:heptadecanoic acid
1749:pentadecanoic acid
838:Chemical structure
829:
432:Chemical structure
423:
421:
313:
293:Comparison of the
247:cholesteryl esters
208:, particularly in
202:
6335:
6334:
6331:
6330:
6183:
6182:
5704:Nonatriacontanoic
5698:Octatriacontanoic
5047:978-0-471-46159-3
4863:10.1242/jeb.00399
4817:(Pt 22): 3561–9.
4600:978-0-471-21495-3
4542:10.1159/000100426
4510:978-0-7167-2009-6
4351:978-0-08-022369-8
4294:(15): 1248–1259.
4288:The FASEB Journal
4124:978-1-118-16945-2
4099:978-2-8041-8175-8
4069:Cyberlipid Center
4029:Annales de Chimie
3774:diethylene glycol
3683:atopic dermatitis
3603:Blood fatty acids
3511:citric acid cycle
3212:
3211:
2684:citric acid cycle
2609:ATP citrate lyase
2605:citric acid cycle
2488:transport protein
2461:
2460:
1957:ends with –CH=CH–
1945:(18 carbons, Δ),
1918:) corresponds to
1739:
1738:
695:
694:
182:
181:
134:Fat hydrogenation
126:Manufactured fats
16:(Redirected from
6370:
6275:
6210:
6203:
6196:
6187:
6154:ω−12 Unsaturated
6135:ω−11 Unsaturated
6116:ω−10 Unsaturated
5819:Eicosapentaenoic
5813:Eicosatetraenoic
5777:Palmitolinolenic
5771:Myristolinolenic
5686:Hexatriacontylic
5461:
5454:
5447:
5438:
5394:
5393:
5377:
5376:
5374:
5372:
5366:
5355:
5347:
5341:
5340:
5312:
5306:
5305:
5276:
5270:
5269:
5259:
5219:
5206:
5205:
5179:
5155:
5138:
5137:
5135:
5134:
5119:
5113:
5112:
5102:
5058:
5052:
5051:
5031:
5025:
5024:
4996:
4990:
4989:
4987:
4986:
4971:
4960:
4959:
4957:
4956:
4940:
4934:
4933:
4925:
4919:
4918:
4882:
4876:
4875:
4865:
4841:
4835:
4834:
4806:
4800:
4799:
4763:
4754:
4753:
4739:
4716:Curr. Pharm. Des
4707:
4701:
4700:
4686:
4657:Tsuji A (2005).
4654:
4648:
4647:
4611:
4605:
4604:
4588:
4578:
4572:
4571:
4565:
4557:
4544:
4529:Hormone Research
4524:
4515:
4514:
4496:
4479:
4478:
4450:
4437:
4436:
4424:
4418:
4417:
4404:
4398:
4397:
4395:
4370:
4364:
4363:
4333:
4322:
4321:
4303:
4279:
4273:
4272:
4262:
4230:
4224:
4223:
4212:
4203:
4202:
4192:
4182:
4154:
4148:
4147:
4135:
4129:
4128:
4110:
4104:
4103:
4083:
4077:
4076:
4071:. Archived from
4060:
4054:
4053:
4043:
4037:
4036:
4020:
4014:
4013:
3977:
3971:
3970:
3968:
3967:
3954:
3930:
3918:
3895:
3884:
3877:
3871:
3868:
3862:
3859:methylene bridge
3851:
3758:anti-foam agents
3625:free fatty acids
3579:endocannabinoids
3573:fatty acids are
3547:six carbon atoms
3376:chelating agents
3270:sodium hydroxide
2780:
2748:warm-bloodedness
2745:
2741:
2464:Free fatty acids
2454:γ-linolenic acid
2450:α-linolenic acid
2430:α-linolenic acid
2421:
2420:
2419:
2308:α-linolenic acid
2121:begins from the
2101:Systematic names
2076:systematic names
2061:Palmitoleic acid
2043:
2016:
2015:
2014:
2004:
2003:
2002:
1992:
1991:
1990:
1980:
1979:
1978:
1968:
1967:
1966:
1928:arachidonic acid
1887:" is written "n−
1824:unbranched chain
1588:Palmitoleic acid
1537:Myristoleic acid
1300:Linoelaidic acid
1222:20:4(5,8,11,14)
1150:Arachidonic acid
968:α-Linolenic acid
832:
764:α-Linolenic acid
426:
403:sodium hydroxide
230:unbranched chain
174:
167:
160:
30:
21:
6378:
6377:
6373:
6372:
6371:
6369:
6368:
6367:
6338:
6337:
6336:
6327:
6306:
6264:
6243:
6222:
6214:
6184:
6179:
6148:
6129:
6110:
6057:ω−9 Unsaturated
6051:
6014:ω−7 Unsaturated
6008:
5973:Dihomo-linoleic
5933:12-Octadecenoic
5927:8-Tetradecenoic
5919:ω−6 Unsaturated
5913:
5868:Palmitovaccenic
5854:ω−5 Unsaturated
5848:
5831:Docosahexaenoic
5765:Myristolinoleic
5759:Myristovaccenic
5721:ω−3 Unsaturated
5715:
5656:Hentriacontylic
5474:
5465:
5415:
5414:
5413:
5395:
5391:
5386:
5381:
5380:
5370:
5368:
5364:
5353:
5349:
5348:
5344:
5314:
5313:
5309:
5278:
5277:
5273:
5234:(16): e159762.
5221:
5220:
5209:
5157:
5156:
5141:
5132:
5130:
5129:. July 21, 2009
5121:
5120:
5116:
5060:
5059:
5055:
5048:
5033:
5032:
5028:
5021:
4998:
4997:
4993:
4984:
4982:
4973:
4972:
4963:
4954:
4952:
4942:
4941:
4937:
4927:
4926:
4922:
4884:
4883:
4879:
4843:
4842:
4838:
4808:
4807:
4803:
4765:
4764:
4757:
4722:(10): 1487–98.
4709:
4708:
4704:
4656:
4655:
4651:
4613:
4612:
4608:
4601:
4580:
4579:
4575:
4558:
4526:
4525:
4518:
4511:
4498:
4497:
4482:
4475:
4452:
4451:
4440:
4426:
4425:
4421:
4406:
4405:
4401:
4372:
4371:
4367:
4352:
4335:
4334:
4325:
4281:
4280:
4276:
4232:
4231:
4227:
4214:
4213:
4206:
4156:
4155:
4151:
4137:
4136:
4132:
4125:
4112:
4111:
4107:
4100:
4085:
4084:
4080:
4062:
4061:
4057:
4045:
4044:
4040:
4022:
4021:
4017:
3979:
3978:
3974:
3965:
3963:
3932:
3931:
3927:
3922:
3921:
3911:
3902:
3900:
3898:
3896:
3887:
3878:
3874:
3869:
3865:
3852:
3843:
3838:
3833:
3789:
3783:
3770:ethylene glycol
3734:
3732:Industrial uses
3695:
3648:stratum corneum
3644:
3605:
3599:
3583:antinociceptive
3538:
3532:
3500:
3495:
3489:
3481:subclavian vein
3431:
3425:
3420:
3409:
3405:
3401:
3397:
3388:
3364:
3362:Rancidification
3358:
3336:
3330:configuration.
3312:rancidification
3305:
3297:
3274:phenolphthalein
3272:solution using
3251:
3239:
3229:
3217:
2972:Palm kernel oil
2791:Polyunsaturated
2788:Monounsaturated
2765:
2743:
2739:
2710:Studies on the
2708:
2689:
2661:Golgi apparatus
2558:
2552:
2520:
2515:
2472:
2466:
2418:
2415:
2414:
2413:
2411:
2384:
2368:
2364:
2249:
2235:
2215:is designated "
2089:
2038:
2013:
2010:
2009:
2008:
2006:
2001:
1998:
1997:
1996:
1994:
1989:
1986:
1985:
1984:
1982:
1977:
1974:
1973:
1972:
1970:
1965:
1962:
1961:
1960:
1958:
1845:(or sometimes C
1796:
1790:
1785:
1761:
1744:
1716:
1712:
1705:
1701:
1697:
1665:
1661:
1654:
1650:
1646:
1614:
1610:
1603:
1599:
1595:
1563:
1559:
1552:
1548:
1544:
1503:
1499:
1492:
1488:
1484:
1450:
1446:
1439:
1435:
1431:
1397:
1393:
1386:
1382:
1378:
1333:
1329:
1322:
1315:
1311:
1307:
1269:
1265:
1258:
1251:
1247:
1243:
1197:
1193:
1186:
1179:
1172:
1165:
1161:
1157:
1096:
1092:
1085:
1078:
1071:
1064:
1057:
1050:
1046:
1004:
1000:
993:
986:
979:
975:
925:
921:
914:
907:
900:
893:
886:
882:
802:configuration (
713:
706:
704:Unsaturated fat
700:
687:
683:
679:
662:
658:
654:
647:Lignoceric acid
637:
633:
629:
612:
608:
604:
587:
583:
579:
562:
558:
554:
537:
533:
529:
512:
508:
504:
487:
483:
479:
462:
458:
454:
388:
384:
380:
375:
368:
362:
321:
287:
263:
218:carboxylic acid
178:
53:Unsaturated fat
28:
27:Carboxylic acid
23:
22:
15:
12:
11:
5:
6376:
6374:
6366:
6365:
6360:
6355:
6350:
6340:
6339:
6333:
6332:
6329:
6328:
6326:
6325:
6320:
6318:Mevalonic acid
6314:
6312:
6308:
6307:
6305:
6304:
6299:
6297:Pristanic acid
6294:
6289:
6283:
6281:
6272:
6266:
6265:
6263:
6262:
6257:
6251:
6249:
6245:
6244:
6242:
6241:
6236:
6230:
6228:
6224:
6223:
6215:
6213:
6212:
6205:
6198:
6190:
6181:
6180:
6178:
6177:
6171:
6165:
6162:4-Hexadecenoic
6158:
6156:
6150:
6149:
6147:
6146:
6139:
6137:
6131:
6130:
6128:
6127:
6120:
6118:
6112:
6111:
6109:
6108:
6102:
6096:
6090:
6084:
6078:
6068:
6061:
6059:
6053:
6052:
6050:
6049:
6043:
6037:
6031:
6025:
6018:
6016:
6010:
6009:
6007:
6006:
6000:
5994:
5988:
5982:
5976:
5970:
5964:
5958:
5952:
5942:
5936:
5930:
5923:
5921:
5915:
5914:
5912:
5911:
5905:
5899:
5893:
5887:
5877:
5871:
5865:
5858:
5856:
5850:
5849:
5847:
5846:
5840:
5834:
5828:
5822:
5816:
5810:
5804:
5798:
5792:
5786:
5780:
5774:
5768:
5762:
5756:
5750:
5744:
5738:
5732:
5725:
5723:
5717:
5716:
5714:
5713:
5710:Tetracontanoic
5707:
5701:
5695:
5689:
5683:
5677:
5671:
5665:
5659:
5653:
5647:
5641:
5635:
5629:
5623:
5617:
5611:
5605:
5599:
5593:
5587:
5581:
5575:
5569:
5563:
5557:
5551:
5545:
5539:
5533:
5527:
5521:
5515:
5509:
5503:
5497:
5491:
5484:
5482:
5476:
5475:
5466:
5464:
5463:
5456:
5449:
5441:
5435:
5434:
5429:
5421:
5402:chemical-class
5396:
5389:
5388:
5387:
5385:
5384:External links
5382:
5379:
5378:
5358:aciscience.org
5342:
5307:
5271:
5207:
5139:
5114:
5077:(8): 707–716.
5053:
5046:
5026:
5020:978-3527306732
5019:
4991:
4961:
4935:
4920:
4877:
4836:
4801:
4755:
4702:
4649:
4622:(3): 333–340.
4606:
4599:
4573:
4516:
4509:
4480:
4474:978-3527306732
4473:
4438:
4419:
4399:
4365:
4350:
4323:
4274:
4245:(4): 730–734.
4225:
4204:
4149:
4130:
4123:
4105:
4098:
4078:
4075:on 2017-10-06.
4055:
4038:
4015:
3972:
3924:
3923:
3920:
3919:
3885:
3872:
3863:
3840:
3839:
3837:
3834:
3832:
3831:
3826:
3821:
3816:
3811:
3806:
3804:Fatty aldehyde
3801:
3796:
3790:
3788:
3785:
3746:fatty alcohols
3742:metallic soaps
3733:
3730:
3694:
3691:
3656:differentiated
3643:
3640:
3601:Main article:
3598:
3595:
3577:precursors to
3534:Main article:
3531:
3528:
3507:beta oxidation
3498:
3491:Main article:
3488:
3485:
3427:Main article:
3424:
3421:
3419:
3416:
3407:
3403:
3399:
3395:
3387:
3384:
3368:auto-oxidation
3360:Main article:
3357:
3354:
3339:fatty alcohols
3334:
3316:higher melting
3303:
3296:
3293:
3289:metallic soaps
3285:saponification
3249:
3237:
3228:
3225:
3221:esterification
3216:
3213:
3210:
3209:
3206:
3203:
3200:
3197:
3194:
3188:
3187:
3184:
3181:
3178:
3175:
3172:
3166:
3165:
3162:
3159:
3156:
3153:
3150:
3144:
3143:
3140:
3137:
3134:
3131:
3128:
3122:
3121:
3118:
3115:
3112:
3109:
3106:
3100:
3099:
3096:
3093:
3090:
3087:
3084:
3078:
3077:
3074:
3071:
3068:
3065:
3062:
3056:
3055:
3052:
3049:
3046:
3043:
3040:
3038:Wheat germ oil
3034:
3033:
3030:
3027:
3024:
3021:
3018:
3016:Cottonseed oil
3012:
3011:
3008:
3005:
3002:
2999:
2996:
2990:
2989:
2986:
2983:
2980:
2977:
2974:
2968:
2967:
2964:
2961:
2958:
2955:
2952:
2946:
2945:
2942:
2939:
2936:
2933:
2930:
2924:
2923:
2920:Vegetable fats
2915:
2914:
2911:
2908:
2905:
2902:
2899:
2893:
2892:
2889:
2886:
2883:
2880:
2877:
2871:
2870:
2867:
2864:
2861:
2858:
2855:
2849:
2848:
2845:
2842:
2839:
2836:
2833:
2827:
2826:
2818:
2817:
2814:
2811:
2808:
2805:
2802:
2799:
2798:
2795:
2792:
2789:
2786:
2783:
2764:
2761:
2712:cell membranes
2707:
2704:
2687:
2680:beta-oxidation
2635:that form the
2570:mammary glands
2566:adipose tissue
2554:Main article:
2551:
2548:
2519:
2516:
2514:
2511:
2465:
2462:
2459:
2458:
2416:
2393:take the form
2388:
2361:
2360:Lipid numbers
2357:
2356:
2255:
2241:
2225:
2224:
2170:
2158:
2154:
2153:
2097:
2084:
2080:
2079:
2063:
2058:
2054:
2053:
2050:
2047:
2037:
2034:
2011:
1999:
1987:
1975:
1963:
1862:Greek alphabet
1828:carboxyl group
1789:
1786:
1784:
1781:
1760:
1757:
1743:
1740:
1737:
1736:
1730:
1727:
1724:
1718:
1714:
1710:
1703:
1699:
1695:
1692:
1686:
1685:
1679:
1676:
1673:
1667:
1663:
1659:
1652:
1648:
1644:
1641:
1635:
1634:
1628:
1625:
1622:
1616:
1612:
1608:
1601:
1597:
1593:
1590:
1584:
1583:
1577:
1574:
1571:
1565:
1561:
1557:
1550:
1546:
1542:
1539:
1533:
1532:
1526:
1525:
1517:
1514:
1511:
1505:
1501:
1497:
1490:
1486:
1482:
1479:
1473:
1472:
1464:
1461:
1458:
1452:
1448:
1444:
1437:
1433:
1429:
1426:
1420:
1419:
1411:
1408:
1405:
1399:
1395:
1391:
1384:
1380:
1376:
1373:
1367:
1366:
1360:
1359:
1351:
1348:
1345:
1335:
1331:
1327:
1320:
1313:
1309:
1305:
1302:
1296:
1295:
1287:
1284:
1281:
1271:
1267:
1263:
1256:
1249:
1245:
1241:
1238:
1232:
1231:
1223:
1220:
1217:
1199:
1195:
1191:
1184:
1177:
1170:
1163:
1159:
1155:
1152:
1146:
1145:
1139:
1138:
1130:
1127:
1124:
1098:
1094:
1090:
1083:
1076:
1069:
1062:
1055:
1048:
1044:
1041:
1035:
1034:
1026:
1025:18:3(9,12,15)
1023:
1020:
1006:
1002:
998:
991:
984:
977:
973:
970:
964:
963:
955:
952:
949:
927:
923:
919:
912:
905:
898:
891:
884:
880:
877:
871:
870:
864:
863:
854:
851:
842:
839:
836:
816:dairy products
784:
783:
772:
767:
736:
702:Main article:
699:
696:
693:
692:
689:
685:
681:
677:
674:
668:
667:
664:
660:
656:
652:
649:
643:
642:
639:
635:
631:
627:
624:
618:
617:
614:
610:
606:
602:
599:
597:Arachidic acid
593:
592:
589:
585:
581:
577:
574:
568:
567:
564:
560:
556:
552:
549:
543:
542:
539:
535:
531:
527:
524:
518:
517:
514:
510:
506:
502:
499:
493:
492:
489:
485:
481:
477:
474:
468:
467:
464:
460:
456:
452:
449:
443:
442:
433:
430:
417:Arachidic acid
386:
382:
378:
364:Main article:
361:
358:
357:
356:
350:
347:
340:
320:
317:
303:(top) and the
286:
283:
262:
259:
200:configuration.
180:
179:
177:
176:
169:
162:
154:
151:
150:
149:
148:
143:
142:
141:
128:
127:
123:
122:
121:
120:
115:
110:
109:
108:
103:
98:
93:
75:
74:
70:
69:
68:
67:
66:
65:
60:
50:
42:
41:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
6375:
6364:
6361:
6359:
6356:
6354:
6351:
6349:
6346:
6345:
6343:
6324:
6321:
6319:
6316:
6315:
6313:
6309:
6303:
6302:Propionyl-CoA
6300:
6298:
6295:
6293:
6292:Phytanoyl-CoA
6290:
6288:
6287:Phytanic acid
6285:
6284:
6282:
6280:
6276:
6273:
6271:
6267:
6261:
6258:
6256:
6253:
6252:
6250:
6246:
6240:
6237:
6235:
6232:
6231:
6229:
6225:
6221:
6218:
6211:
6206:
6204:
6199:
6197:
6192:
6191:
6188:
6175:
6172:
6169:
6166:
6163:
6160:
6159:
6157:
6155:
6151:
6144:
6141:
6140:
6138:
6136:
6132:
6125:
6122:
6121:
6119:
6117:
6113:
6106:
6103:
6100:
6097:
6094:
6091:
6088:
6085:
6082:
6079:
6076:
6072:
6069:
6066:
6063:
6062:
6060:
6058:
6054:
6047:
6044:
6041:
6038:
6035:
6032:
6029:
6026:
6023:
6020:
6019:
6017:
6015:
6011:
6004:
6001:
5998:
5995:
5992:
5989:
5986:
5983:
5980:
5977:
5974:
5971:
5968:
5965:
5962:
5959:
5956:
5953:
5950:
5946:
5943:
5940:
5937:
5934:
5931:
5928:
5925:
5924:
5922:
5920:
5916:
5909:
5906:
5903:
5900:
5897:
5894:
5891:
5888:
5885:
5881:
5880:β-Eleostearic
5878:
5875:
5874:α-Eleostearic
5872:
5869:
5866:
5863:
5860:
5859:
5857:
5855:
5851:
5844:
5841:
5838:
5835:
5832:
5829:
5826:
5823:
5820:
5817:
5814:
5811:
5808:
5805:
5802:
5799:
5796:
5793:
5790:
5787:
5784:
5781:
5778:
5775:
5772:
5769:
5766:
5763:
5760:
5757:
5754:
5753:Laurolinoleic
5751:
5748:
5745:
5742:
5739:
5736:
5733:
5730:
5727:
5726:
5724:
5722:
5718:
5711:
5708:
5705:
5702:
5699:
5696:
5693:
5690:
5687:
5684:
5681:
5678:
5675:
5672:
5669:
5666:
5663:
5660:
5657:
5654:
5651:
5648:
5645:
5642:
5639:
5636:
5633:
5630:
5627:
5624:
5621:
5618:
5615:
5612:
5609:
5606:
5603:
5600:
5597:
5594:
5591:
5588:
5585:
5582:
5579:
5576:
5573:
5570:
5567:
5564:
5561:
5558:
5555:
5552:
5549:
5546:
5543:
5540:
5537:
5534:
5531:
5528:
5525:
5522:
5519:
5516:
5513:
5510:
5507:
5504:
5501:
5498:
5495:
5492:
5489:
5486:
5485:
5483:
5481:
5477:
5473:
5469:
5462:
5457:
5455:
5450:
5448:
5443:
5442:
5439:
5433:
5430:
5428:
5426:
5422:
5420:
5419:Lipid Library
5417:
5416:
5411:
5410:
5409:
5403:
5399:
5383:
5363:
5359:
5352:
5346:
5343:
5338:
5334:
5330:
5326:
5322:
5318:
5311:
5308:
5303:
5299:
5295:
5291:
5288:(1): E101-7.
5287:
5283:
5275:
5272:
5267:
5263:
5258:
5253:
5249:
5245:
5241:
5237:
5233:
5229:
5225:
5218:
5216:
5214:
5212:
5208:
5203:
5199:
5195:
5191:
5187:
5183:
5178:
5173:
5169:
5165:
5161:
5154:
5152:
5150:
5148:
5146:
5144:
5140:
5128:
5127:Science Daily
5124:
5118:
5115:
5110:
5106:
5101:
5096:
5092:
5088:
5084:
5080:
5076:
5072:
5068:
5064:
5057:
5054:
5049:
5043:
5039:
5038:
5030:
5027:
5022:
5016:
5012:
5008:
5004:
5003:
4995:
4992:
4981:on 2015-03-03
4980:
4976:
4970:
4968:
4966:
4962:
4951:on 2010-12-05
4950:
4946:
4939:
4936:
4931:
4924:
4921:
4916:
4912:
4908:
4904:
4900:
4896:
4892:
4888:
4881:
4878:
4873:
4869:
4864:
4859:
4855:
4851:
4847:
4840:
4837:
4832:
4828:
4824:
4820:
4816:
4812:
4805:
4802:
4797:
4793:
4789:
4785:
4781:
4777:
4774:(3): 257–74.
4773:
4769:
4762:
4760:
4756:
4752:
4747:
4743:
4738:
4733:
4729:
4725:
4721:
4717:
4713:
4706:
4703:
4699:
4694:
4690:
4685:
4680:
4676:
4672:
4668:
4664:
4660:
4653:
4650:
4645:
4641:
4637:
4633:
4629:
4625:
4621:
4617:
4610:
4607:
4602:
4596:
4592:
4587:
4586:
4577:
4574:
4569:
4563:
4556:
4552:
4548:
4543:
4538:
4534:
4530:
4523:
4521:
4517:
4512:
4506:
4502:
4495:
4493:
4491:
4489:
4487:
4485:
4481:
4476:
4470:
4466:
4462:
4458:
4457:
4449:
4447:
4445:
4443:
4439:
4434:
4430:
4423:
4420:
4415:
4411:
4410:
4403:
4400:
4394:
4389:
4385:
4381:
4380:
4375:
4369:
4366:
4361:
4357:
4353:
4347:
4343:
4339:
4332:
4330:
4328:
4324:
4319:
4315:
4311:
4307:
4302:
4297:
4293:
4289:
4285:
4278:
4275:
4270:
4266:
4261:
4256:
4252:
4248:
4244:
4240:
4236:
4229:
4226:
4221:
4217:
4211:
4209:
4205:
4200:
4196:
4191:
4186:
4181:
4176:
4172:
4168:
4164:
4162:
4153:
4150:
4145:
4141:
4134:
4131:
4126:
4120:
4116:
4109:
4106:
4101:
4095:
4091:
4090:
4082:
4079:
4074:
4070:
4066:
4059:
4056:
4051:
4050:
4042:
4039:
4034:
4030:
4026:
4019:
4016:
4011:
4007:
4003:
3999:
3995:
3991:
3987:
3983:
3976:
3973:
3962:
3958:
3953:
3948:
3944:
3940:
3936:
3929:
3926:
3916:
3910:
3906:
3894:
3892:
3890:
3886:
3882:
3876:
3873:
3867:
3864:
3860:
3856:
3850:
3848:
3846:
3842:
3835:
3830:
3827:
3825:
3824:Vegetable oil
3822:
3820:
3817:
3815:
3812:
3810:
3807:
3805:
3802:
3800:
3797:
3795:
3792:
3791:
3786:
3784:
3781:
3779:
3775:
3771:
3767:
3761:
3759:
3755:
3751:
3747:
3743:
3739:
3731:
3729:
3727:
3723:
3719:
3714:
3712:
3708:
3704:
3700:
3692:
3690:
3688:
3684:
3680:
3676:
3672:
3668:
3664:
3661:
3657:
3653:
3649:
3641:
3639:
3637:
3633:
3628:
3626:
3622:
3618:
3614:
3610:
3604:
3596:
3594:
3592:
3588:
3584:
3580:
3576:
3572:
3568:
3564:
3560:
3556:
3552:
3551:linoleic acid
3548:
3544:
3537:
3529:
3527:
3524:
3520:
3516:
3512:
3508:
3504:
3494:
3486:
3484:
3482:
3478:
3477:thoracic duct
3474:
3470:
3465:
3463:
3459:
3455:
3454:triglycerides
3451:
3447:
3443:
3439:
3435:
3430:
3422:
3417:
3415:
3413:
3393:
3385:
3383:
3381:
3377:
3373:
3369:
3363:
3355:
3353:
3351:
3346:
3344:
3340:
3331:
3329:
3325:
3321:
3317:
3313:
3309:
3308:iodine number
3301:
3300:Hydrogenation
3294:
3292:
3290:
3286:
3281:
3279:
3275:
3271:
3267:
3263:
3258:
3256:
3248:
3244:
3243:Nonanoic acid
3240:
3236:
3226:
3224:
3222:
3214:
3193:
3190:
3189:
3171:
3168:
3167:
3149:
3148:Safflower oil
3146:
3145:
3127:
3126:Sunflower oil
3124:
3123:
3105:
3102:
3101:
3083:
3080:
3079:
3061:
3058:
3057:
3039:
3036:
3035:
3017:
3014:
3013:
2995:
2992:
2991:
2973:
2970:
2969:
2951:
2948:
2947:
2929:
2926:
2925:
2922:
2921:
2916:
2898:
2895:
2894:
2876:
2873:
2872:
2854:
2851:
2850:
2832:
2829:
2828:
2825:
2824:
2819:
2801:
2800:
2796:
2793:
2790:
2787:
2784:
2782:
2781:
2776:
2774:
2770:
2762:
2760:
2758:
2753:
2749:
2737:
2733:
2729:
2725:
2721:
2717:
2713:
2705:
2703:
2701:
2697:
2693:
2685:
2681:
2677:
2673:
2669:
2664:
2662:
2658:
2654:
2650:
2646:
2642:
2638:
2634:
2633:phospholipids
2630:
2629:triglycerides
2624:
2622:
2618:
2614:
2610:
2606:
2602:
2598:
2594:
2590:
2589:mitochondrion
2586:
2582:
2578:
2573:
2571:
2567:
2563:
2557:
2549:
2547:
2545:
2541:
2540:Phospholipids
2537:
2536:oleochemicals
2533:
2529:
2528:triglycerides
2525:
2517:
2512:
2510:
2508:
2504:
2500:
2495:
2493:
2489:
2485:
2481:
2477:
2471:
2463:
2455:
2451:
2447:
2443:
2439:
2435:
2431:
2427:
2423:
2408:
2404:
2400:
2396:
2392:
2391:Lipid numbers
2389:
2387:
2386:18:3(9,12,15)
2383:
2381:
2377:
2373:
2367:
2362:
2359:
2358:
2354:
2352:
2347:
2345:
2340:
2336:
2332:
2328:
2324:
2320:
2316:
2314:
2309:
2305:
2301:
2297:
2293:
2289:
2288:
2282:
2281:
2275:
2274:
2270:
2265:
2264:
2260:
2256:
2253:
2248:
2246:
2242:
2239:
2234:
2230:
2227:
2226:
2222:
2218:
2214:
2213:linoleic acid
2210:
2209:
2204:
2203:
2198:
2194:
2190:
2186:
2182:
2181:
2175:
2171:
2169:
2167:
2163:
2159:
2156:
2155:
2151:
2150:
2145:
2144:
2139:
2137:
2133:
2128:
2124:
2120:
2116:
2115:
2110:
2108:
2103:
2102:
2098:
2096:
2094:
2088:
2085:
2082:
2081:
2077:
2073:
2069:
2068:
2067:Trivial names
2064:
2062:
2059:
2056:
2055:
2051:
2048:
2046:Nomenclature
2045:
2044:
2041:
2035:
2033:
2031:
2027:
2023:
2018:
1956:
1952:
1950:
1944:
1943:linoleic acid
1940:
1936:
1931:
1929:
1925:
1921:
1917:
1913:
1909:
1904:
1901:
1897:
1892:
1890:
1886:
1882:
1877:
1875:
1871:
1867:
1863:
1858:
1856:
1852:
1848:
1844:
1840:
1835:
1833:
1829:
1825:
1817:
1813:
1809:
1805:
1800:
1795:
1787:
1782:
1780:
1778:
1777:methyl groups
1774:
1770:
1766:
1758:
1756:
1754:
1750:
1747:derivatives,
1741:
1734:
1731:
1728:
1725:
1722:
1719:
1708:
1693:
1691:
1690:Sapienic acid
1688:
1687:
1683:
1680:
1677:
1674:
1671:
1668:
1657:
1642:
1640:
1639:Vaccenic acid
1637:
1636:
1632:
1629:
1626:
1623:
1620:
1617:
1606:
1591:
1589:
1586:
1585:
1581:
1578:
1575:
1572:
1569:
1566:
1555:
1540:
1538:
1535:
1534:
1531:
1527:
1524:
1522:
1518:
1515:
1512:
1509:
1506:
1495:
1480:
1478:
1475:
1474:
1471:
1469:
1465:
1462:
1459:
1456:
1453:
1442:
1427:
1425:
1422:
1421:
1418:
1416:
1412:
1409:
1406:
1403:
1400:
1389:
1374:
1372:
1369:
1368:
1365:
1361:
1358:
1356:
1352:
1350:18:2(9t,12t)
1349:
1346:
1343:
1339:
1336:
1325:
1318:
1303:
1301:
1298:
1297:
1294:
1292:
1288:
1285:
1282:
1279:
1275:
1272:
1261:
1254:
1239:
1237:
1236:Linoleic acid
1234:
1233:
1230:
1228:
1224:
1221:
1218:
1215:
1211:
1207:
1203:
1200:
1189:
1182:
1175:
1168:
1153:
1151:
1148:
1147:
1144:
1140:
1137:
1135:
1131:
1128:
1125:
1123:-Δ,Δ,Δ,Δ,Δ,Δ
1122:
1118:
1114:
1110:
1106:
1102:
1099:
1088:
1081:
1074:
1067:
1060:
1053:
1042:
1040:
1037:
1036:
1033:
1031:
1027:
1024:
1021:
1018:
1014:
1010:
1007:
996:
989:
982:
971:
969:
966:
965:
962:
960:
956:
953:
950:
947:
943:
939:
935:
931:
928:
917:
910:
903:
896:
889:
878:
876:
873:
872:
869:
865:
862:
858:
855:
852:
850:
846:
843:
840:
837:
834:
833:
827:
823:
821:
817:
813:
809:
808:hydrogenation
805:
801:
797:
793:
789:
781:
777:
773:
771:
768:
765:
761:
760:linoleic acid
757:
753:
749:
745:
741:
737:
735:
732:
731:
730:
728:
727:
723:
718:
711:
705:
697:
690:
675:
673:
670:
669:
665:
650:
648:
645:
644:
640:
625:
623:
620:
619:
615:
600:
598:
595:
594:
590:
575:
573:
570:
569:
565:
550:
548:
547:Palmitic acid
545:
544:
540:
525:
523:
522:Myristic acid
520:
519:
515:
500:
498:
495:
494:
490:
475:
473:
470:
469:
465:
450:
448:
447:Caprylic acid
445:
444:
441:
437:
434:
431:
428:
427:
418:
414:
410:
408:
404:
400:
396:
392:
373:
367:
366:Saturated fat
359:
354:
351:
348:
345:
341:
338:
334:
330:
326:
323:
322:
318:
316:
310:
306:
302:
299:
297:
291:
284:
282:
280:
279:acide huileux
276:
275:graisse acide
272:
268:
260:
258:
256:
252:
248:
244:
243:phospholipids
240:
239:triglycerides
236:
231:
227:
223:
219:
215:
211:
207:
199:
195:
191:
186:
175:
170:
168:
163:
161:
156:
155:
153:
152:
147:
144:
140:
137:
136:
135:
132:
131:
130:
129:
124:
119:
116:
114:
111:
107:
104:
102:
99:
97:
94:
92:
89:
88:
86:
82:
79:
78:
77:
76:
71:
64:
61:
59:
56:
55:
54:
51:
49:
48:Saturated fat
46:
45:
44:
43:
40:
36:
31:
19:
6216:
6174:8-Eicosenoic
6168:Petroselinic
6074:
5948:
5945:Linolelaidic
5883:
5825:Clupanodonic
5783:Palmitidonic
5620:Pentacosylic
5596:Heneicosylic
5560:Pentadecylic
5471:
5424:
5406:
5405:
5404:profile for
5401:
5369:. Retrieved
5357:
5345:
5323:(7): 302–6.
5320:
5316:
5310:
5285:
5281:
5274:
5231:
5227:
5167:
5163:
5131:. Retrieved
5126:
5117:
5074:
5070:
5056:
5036:
5029:
5000:
4994:
4983:. Retrieved
4979:the original
4953:. Retrieved
4949:the original
4943:Altar, Ted.
4938:
4929:
4923:
4890:
4886:
4880:
4853:
4849:
4839:
4814:
4810:
4804:
4771:
4767:
4751:astrocytes .
4749:
4719:
4715:
4705:
4696:
4669:(1): 54–62.
4666:
4662:
4652:
4619:
4615:
4609:
4584:
4576:
4562:cite journal
4554:
4535:(2): 72–82.
4532:
4528:
4501:Biochemistry
4500:
4454:
4432:
4422:
4408:
4402:
4383:
4377:
4368:
4337:
4291:
4287:
4277:
4242:
4238:
4228:
4219:
4170:
4166:
4160:
4152:
4143:
4133:
4114:
4108:
4088:
4081:
4073:the original
4068:
4058:
4048:
4041:
4032:
4028:
4018:
3985:
3981:
3975:
3964:. Retrieved
3942:
3938:
3928:
3880:
3875:
3866:
3854:
3782:
3762:
3750:fatty amines
3735:
3715:
3696:
3685:, and other
3645:
3636:pyruvic acid
3629:
3609:chylomicrons
3606:
3597:Distribution
3593:properties.
3575:biosynthetic
3539:
3503:mitochondria
3496:
3466:
3432:
3392:azelaic acid
3389:
3365:
3347:
3332:
3327:
3323:
3298:
3282:
3259:
3246:
3234:
3230:
3218:
2950:Cocoa butter
2919:
2918:
2822:
2821:
2766:
2757:temperatures
2709:
2665:
2653:mitochondria
2625:
2601:oxaloacetate
2574:
2559:
2546:of alkenes.
2521:
2499:triglyceride
2496:
2473:
2445:
2441:
2437:
2433:
2425:
2406:
2402:
2398:
2394:
2390:
2379:
2375:
2371:
2350:
2343:
2338:
2334:
2326:
2322:
2312:
2295:
2292:nomenclature
2291:
2286:
2284:
2279:
2277:
2272:
2268:
2267:
2262:
2258:
2257:
2244:
2237:
2232:
2228:
2220:
2216:
2206:
2200:
2188:
2185:nomenclature
2184:
2179:
2177:
2173:
2165:
2161:
2147:
2141:
2140:notation or
2135:
2131:
2127:Double bonds
2112:
2105:
2099:
2092:
2075:
2072:common names
2071:
2065:
2052:Explanation
2039:
2019:
1948:
1937:such as the
1932:
1923:
1911:
1907:
1905:
1899:
1893:
1888:
1884:
1878:
1865:
1859:
1850:
1846:
1842:
1838:
1836:
1832:methyl group
1821:
1815:
1807:
1803:
1783:Nomenclature
1762:
1745:
1732:
1720:
1706:
1681:
1669:
1655:
1630:
1618:
1604:
1579:
1567:
1553:
1529:
1520:
1507:
1493:
1467:
1454:
1440:
1424:Elaidic acid
1414:
1401:
1387:
1363:
1354:
1341:
1337:
1323:
1316:
1290:
1277:
1273:
1259:
1252:
1226:
1213:
1209:
1205:
1201:
1187:
1180:
1173:
1166:
1142:
1133:
1120:
1116:
1112:
1108:
1104:
1100:
1086:
1079:
1072:
1065:
1058:
1051:
1029:
1016:
1012:
1008:
994:
987:
980:
958:
945:
941:
937:
933:
929:
915:
908:
901:
894:
887:
867:
860:
856:
848:
844:
824:
799:
794:), or nine (
785:
779:
775:
769:
751:
747:
743:
739:
733:
725:
721:
717:double bonds
714:
672:Cerotic acid
622:Behenic acid
572:Stearic acid
439:
435:
398:
395:stearic acid
390:
376:
337:butyric acid
314:
304:
301:elaidic acid
295:
278:
274:
266:
264:
213:
210:biochemistry
203:
113:Triglyceride
80:
6348:Fatty acids
6270:Peroxisomal
6248:Degradation
6239:Malonyl-CoA
6022:Palmitoleic
5991:Arachidonic
5955:γ-Linolenic
5862:Myristoleic
5801:α-Parinaric
5795:Stearidonic
5789:α-Linolenic
5741:Decadienoic
5680:Ceroplastic
5644:Nonacosylic
5584:Nonadecylic
5472:fatty acids
5228:JCI Insight
3988:: 208–214.
3855:unsaturated
3754:emulsifiers
3667:cholesterol
3663:corneocytes
3632:lactic acid
3615:(VLDL) and
3462:chylomicron
3458:cholesterol
3442:portal vein
3418:Circulation
3380:citric acid
3060:Soybean oil
2928:Coconut oil
2823:Animal fats
2794:Cholesterol
2773:cholesterol
2621:malonyl-CoA
2476:circulating
2370:18:3,
2083:Systematic
1896:double bond
1769:side groups
1477:Erucic acid
1286:18:2(9,12)
948:-Δ,Δ,Δ,Δ,Δ
835:Common name
820:breast milk
497:Lauric acid
472:Capric acid
429:Common name
194:Unsaturated
118:Cholesterol
6342:Categories
6260:Acetyl-CoA
6234:Acetyl-CoA
6217:Fatty acid
5632:Carboceric
5614:Lignoceric
5608:Tricosylic
5548:Tridecylic
5524:Pelargonic
5408:Fatty acid
5170:: 105055.
5133:2010-05-18
4985:2010-02-17
4955:2006-08-31
3966:2007-10-31
3836:References
3726:silica gel
3660:enucleated
3621:adipocytes
3591:neurogenic
3587:anxiolytic
3565:(EPA) and
3487:Metabolism
3412:oleic acid
3386:Ozonolysis
3372:tocopherol
3278:hydrolyzed
2797:Vitamin E
2659:, and the
2645:organelles
2585:acetyl-CoA
2581:glycolysis
2568:, and the
2550:By animals
2524:hydrolysis
2518:Industrial
2513:Production
2490:, such as
2468:See also:
2197:carboxylic
2123:carboxylic
2022:odd number
1792:See also:
1678:18:1(11t)
1371:Oleic acid
804:trans fats
756:oleic acid
309:oleic acid
267:acide gras
214:fatty acid
81:Fatty acid
73:Components
6227:Synthesis
6040:Paullinic
5985:Sciadonic
5967:Pinolenic
5747:Lauroleic
5662:Lacceroic
5590:Arachidic
5536:Undecylic
5488:Propionic
5480:Saturated
5248:2379-3708
5202:231864420
5186:0009-3084
5091:1526-5900
3881:n minus x
3679:psoriasis
3671:ceramides
3652:epidermis
3553:(LA) and
3469:lymphatic
3320:margarine
3082:Olive oil
2785:Saturated
2769:vitamin E
2668:lipolysis
2641:cell wall
2507:biodiesel
2302:from the
2049:Examples
1922:"D", for
1759:Branching
812:ruminants
729:isomers.
329:aliphatic
222:aliphatic
206:chemistry
190:Saturated
139:Trans fat
33:Types of
6255:Acyl-CoA
6143:Gadoleic
6124:Sapienic
6093:Nervonic
6028:Vaccenic
5961:Calendic
5939:Linoleic
5735:Decenoic
5729:Octenoic
5650:Melissic
5638:Montanic
5572:Margaric
5566:Palmitic
5554:Myristic
5518:Caprylic
5512:Enanthic
5362:Archived
5302:25471637
5266:35900871
5194:33561467
5109:25958314
4915:24441498
4872:12796449
4831:12364409
4796:10433891
4746:23789956
4693:15717057
4644:35349649
4636:15891395
4591:547, 556
4551:17344645
4414:Elsevier
4342:Pergamon
4318:22853095
4269:27422507
4199:14622442
4144:Medscape
4010:22401712
3961:95004254
3787:See also
3766:sorbitol
3709:and mid-
3693:Analysis
3509:and the
3505:through
3378:such as
3266:titrated
3170:Hemp oil
3104:Corn oil
2994:Palm oil
2831:Duck fat
2816:mg/100g
2732:reptiles
2720:reptiles
2577:pyruvate
2532:glycerol
2401:, where
2325:, omega-
2300:counting
2193:counting
2057:Trivial
1947:γ-linole
1900:carboxyl
1849:), with
1516:22:1(13)
1463:18:1(9t)
1364:Omega-9:
1216:-ΔΔ,Δ,Δ
1143:Omega-6:
868:Omega-3:
790:), six (
780:opposite
311:(bottom)
220:with an
6081:Gondoic
6071:Elaidic
6034:Rumenic
5997:Adrenic
5890:Punicic
5668:Psyllic
5626:Cerotic
5602:Behenic
5578:Stearic
5506:Caproic
5500:Valeric
5494:Butyric
5427:journal
5398:Scholia
5337:3611285
5257:9462509
5100:4522350
4907:2035703
4776:Bibcode
4737:4084603
4663:NeuroRx
4360:5008199
4310:8001737
4260:4942867
3990:Bibcode
3571:omega-6
3523:glucose
3473:lacteal
3410:) from
3348:In the
3264:can be
3262:ethanol
3227:Acidity
3054:136.65
2813:mg/100g
2736:omega-6
2730:) than
2716:mammals
2672:albumin
2649:nucleus
2597:citrate
2593:cytosol
2587:in the
2492:albumin
2478:in the
2319:omega-3
2276:; also
1955:formula
1951:ic acid
1941:. Thus
1814:with a
1729:16:1(6)
1627:16:1(9)
1576:14:1(9)
1410:18:1(9)
1019:-Δ,Δ,Δ
333:carbons
307:isomer
261:History
251:dietary
106:Omega-9
101:Omega-7
96:Omega-6
91:Omega-3
6279:Phytol
6176:(20:1)
6170:(18:1)
6164:(16:1)
6145:(20:1)
6126:(16:1)
6107:(20:3)
6101:(20:2)
6095:(24:1)
6089:(22:1)
6087:Erucic
6083:(20:1)
6077:-18:1)
6067:(18:1)
6048:(20:3)
6042:(20:1)
6036:(18:2)
6030:(18:1)
6024:(16:1)
6005:(22:5)
6003:Osbond
5999:(22:4)
5993:(20:4)
5987:(20:3)
5981:(20:3)
5975:(20:2)
5969:(18:3)
5963:(18:3)
5957:(18:3)
5951:-18:2)
5941:(18:2)
5935:(18:1)
5929:(14:1)
5910:(20:4)
5904:(20:3)
5898:(18:3)
5892:(18:3)
5886:-18:3)
5876:(18:3)
5870:(16:1)
5864:(14:1)
5845:(24:6)
5839:(24:5)
5833:(22:6)
5827:(22:5)
5821:(20:5)
5815:(20:4)
5809:(20:3)
5803:(18:4)
5797:(18:4)
5791:(18:3)
5785:(16:4)
5779:(16:3)
5773:(14:3)
5767:(14:2)
5761:(14:1)
5755:(12:2)
5749:(12:1)
5743:(10:2)
5737:(10:1)
5674:Geddic
5542:Lauric
5530:Capric
5468:Lipids
5400:has a
5371:22 Apr
5335:
5300:
5264:
5254:
5246:
5200:
5192:
5184:
5107:
5097:
5089:
5044:
5017:
4913:
4905:
4870:
4829:
4794:
4744:
4734:
4691:
4684:539320
4681:
4642:
4634:
4597:
4549:
4507:
4471:
4358:
4348:
4316:
4308:
4267:
4257:
4197:
4190:317357
4187:
4173:: 10.
4121:
4096:
4008:
3959:
3776:, and
3703:methyl
3589:, and
3434:Short-
3343:esters
3208:22.21
3186:12.34
3164:40.68
3142:49.00
3120:17.24
3076:16.29
3032:42.77
3010:33.12
2897:Butter
2875:Tallow
2810:g/100g
2807:g/100g
2804:g/100g
2742:&
2651:, the
2613:malate
2503:rancid
2480:plasma
2382:-Δ,Δ,Δ
2366:18:3n3
2304:methyl
2285:omega-
2271:minus
2236:(or ω−
2178:delta-
335:(e.g.
298:isomer
245:, and
235:esters
6311:Other
6075:trans
6065:Oleic
5949:trans
5884:trans
5731:(8:1)
5712:(C40)
5706:(C39)
5700:(C38)
5694:(C37)
5688:(C36)
5682:(C35)
5676:(C34)
5670:(C33)
5664:(C32)
5658:(C31)
5652:(C30)
5646:(C29)
5640:(C28)
5634:(C27)
5628:(C26)
5622:(C25)
5616:(C24)
5610:(C23)
5604:(C22)
5598:(C21)
5592:(C20)
5586:(C19)
5580:(C18)
5574:(C17)
5568:(C16)
5562:(C15)
5556:(C14)
5550:(C13)
5544:(C12)
5538:(C11)
5532:(C10)
5365:(PDF)
5354:(PDF)
5198:S2CID
4911:S2CID
4640:S2CID
4314:S2CID
3957:S2CID
3581:with
3450:villi
3328:trans
3268:with
3098:5.10
2988:3.80
2913:2.00
2891:2.70
2869:0.60
2847:2.70
2686:to CO
2619:into
2562:liver
2534:(see
2484:ester
2474:When
2422:units
2331:IUPAC
2208:trans
2205:- or
2195:from
2136:trans
2109:names
2107:IUPAC
1920:Roman
1916:delta
1881:omega
1870:alpha
1866:after
1855:IUPAC
1707:CH=CH
1675:18:1
1670:trans
1666:COOH
1656:CH=CH
1605:CH=CH
1554:CH=CH
1494:CH=CH
1455:trans
1441:CH=CH
1388:CH=CH
1347:18:2
1344:-Δ,Δ
1342:trans
1338:trans
1334:COOH
1324:CH=CH
1317:CH=CH
1283:18:2
1280:-Δ,Δ
1270:COOH
1260:CH=CH
1253:CH=CH
1219:20:4
1198:COOH
1188:CH=CH
1181:CH=CH
1174:CH=CH
1167:CH=CH
1126:22:6
1097:COOH
1087:CH=CH
1080:CH=CH
1073:CH=CH
1066:CH=CH
1059:CH=CH
1052:CH=CH
1022:18:3
1005:COOH
995:CH=CH
988:CH=CH
981:CH=CH
951:20:5
926:COOH
916:CH=CH
909:CH=CH
902:CH=CH
895:CH=CH
888:CH=CH
853:IUPAC
800:trans
776:trans
770:trans
726:trans
691:26:0
666:24:0
641:22:0
616:20:0
591:18:0
566:16:0
541:14:0
516:12:0
491:10:0
296:trans
255:cells
216:is a
198:trans
6105:Mead
5526:(C9)
5520:(C8)
5514:(C7)
5508:(C6)
5502:(C5)
5496:(C4)
5490:(C3)
5373:2018
5333:PMID
5298:PMID
5262:PMID
5244:ISSN
5190:PMID
5182:ISSN
5105:PMID
5087:ISSN
5042:ISBN
5015:ISBN
4903:PMID
4868:PMID
4827:PMID
4792:PMID
4742:PMID
4689:PMID
4632:PMID
4595:ISBN
4568:link
4547:PMID
4505:ISBN
4469:ISBN
4356:OCLC
4346:ISBN
4306:PMID
4265:PMID
4195:PMID
4119:ISBN
4094:ISBN
4006:PMID
3861:(s).
3748:and
3738:soap
3669:and
3658:and
3646:The
3642:Skin
3634:and
3436:and
3394:((CH
3202:24.8
3199:64.3
3158:72.1
3155:12.6
3152:10.2
3136:63.0
3133:20.2
3130:11.9
3114:57.8
3111:24.7
3108:12.7
3092:11.2
3089:69.7
3086:14.0
3070:56.5
3067:23.2
3064:14.5
3048:60.7
3045:15.9
3042:18.8
3026:48.1
3023:21.3
3020:25.5
3001:41.6
2998:45.3
2979:11.4
2976:81.5
2966:1.8
2957:32.9
2954:60.0
2944:.66
2932:85.2
2904:19.8
2901:54.0
2882:41.8
2879:49.8
2860:43.8
2857:40.8
2853:Lard
2841:12.9
2838:49.3
2835:33.2
2771:and
2752:fish
2718:and
2698:and
2452:and
2426:i.e.
2363:18:3
2348:and
2250:(or
2219:-Δ,
2176:(or
2164:-Δ,
2104:(or
2070:(or
1874:beta
1751:and
1735:−10
1726:16:1
1717:COOH
1624:16:1
1615:COOH
1573:14:1
1564:COOH
1513:22:1
1504:COOH
1460:18:1
1451:COOH
1407:18:1
1398:COOH
688:COOH
663:COOH
638:COOH
613:COOH
588:COOH
563:COOH
538:COOH
513:COOH
488:COOH
466:8:0
463:COOH
407:soap
277:and
212:, a
39:food
35:fats
5325:doi
5290:doi
5252:PMC
5236:doi
5172:doi
5168:236
5095:PMC
5079:doi
5007:doi
4895:doi
4891:260
4858:doi
4854:206
4819:doi
4815:205
4784:doi
4772:199
4732:PMC
4724:doi
4679:PMC
4671:doi
4624:doi
4537:doi
4461:doi
4388:doi
4296:doi
4255:PMC
4247:doi
4185:PMC
4175:doi
3998:doi
3986:111
3947:doi
3905:doi
3879:In
3519:ATP
3402:(CO
3326:to
3324:cis
3196:5.3
3004:8.3
2982:1.6
2960:3.0
2938:1.7
2935:6.6
2910:230
2907:2.6
2888:109
2885:4.0
2863:9.6
2844:100
2724:DHA
2714:of
2663:).
2579:by
2538:).
2526:of
2380:cis
2376:cis
2372:cis
2317:or
2283:or
2252:ω−3
2221:cis
2217:cis
2202:cis
2172:In
2166:cis
2162:cis
2132:cis
1816:cis
1721:cis
1709:(CH
1698:(CH
1684:−7
1672:-Δ
1658:(CH
1647:(CH
1633:−7
1619:cis
1607:(CH
1596:(CH
1582:−5
1568:cis
1556:(CH
1545:(CH
1508:cis
1496:(CH
1485:(CH
1443:(CH
1432:(CH
1402:cis
1390:(CH
1379:(CH
1326:(CH
1308:(CH
1278:cis
1274:cis
1262:(CH
1244:(CH
1214:cis
1210:cis
1206:cis
1202:cis
1190:(CH
1158:(CH
1121:cis
1117:cis
1113:cis
1109:cis
1105:cis
1101:cis
1089:(CH
1017:cis
1013:cis
1009:cis
997:(CH
946:cis
942:cis
938:cis
934:cis
930:cis
918:(CH
796:n-9
792:n-6
788:n-3
752:cis
748:cis
744:cis
740:cis
734:cis
724:or
722:cis
680:(CH
655:(CH
630:(CH
605:(CH
580:(CH
555:(CH
530:(CH
505:(CH
480:(CH
455:(CH
381:(CH
305:cis
204:In
37:in
6344::
5470::
5356:.
5331:.
5321:25
5319:.
5296:.
5286:80
5284:.
5260:.
5250:.
5242:.
5230:.
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5210:^
5196:.
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5180:.
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5093:.
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5073:.
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4758:^
4748:.
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4718:.
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4677:.
4665:.
4661:.
4638:.
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4620:16
4618:.
4593:.
4564:}}
4560:{{
4553:.
4533:68
4531:.
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4483:^
4467:.
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4431:.
4412:.
4384:79
4382:.
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4290:.
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4218:.
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4193:.
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4165:.
4142:.
4067:.
4033:88
4031:.
4027:.
4004:.
3996:.
3984:.
3955:.
3943:67
3941:.
3937:.
3888:^
3844:^
3772:,
3768:,
3713:.
3689:.
3681:,
3627:.
3585:,
3561:—
3464:.
3414:.
3406:H)
3345:.
3291:.
3280:.
3255:pH
3241:.
3180:75
3177:15
3174:10
2866:93
2759:.
2744:Na
2726:,
2655:,
2564:,
2494:.
2424:,
2412:CH
2355:.
2353:−6
2346:−3
2315:−3
2290:)
2278:ω−
2254:)
2247:−3
2240:)
2183:)
2157:Δ
2146:-/
2134:-/
2091:(9
2032:.
2017:.
2007:CH
1995:CH
1983:CH
1971:CH
1959:CH
1857:.
1723:-Δ
1694:CH
1643:CH
1621:-Δ
1592:CH
1570:-Δ
1541:CH
1523:−9
1510:-Δ
1502:11
1481:CH
1470:−9
1457:-Δ
1428:CH
1417:−9
1404:-Δ
1375:CH
1357:−6
1319:CH
1304:CH
1293:−6
1255:CH
1240:CH
1229:−6
1183:CH
1176:CH
1169:CH
1154:CH
1136:−3
1082:CH
1075:CH
1068:CH
1061:CH
1054:CH
1047:CH
1043:CH
1032:−3
990:CH
983:CH
976:CH
972:CH
961:−3
911:CH
904:CH
897:CH
890:CH
883:CH
879:CH
774:A
738:A
686:24
676:CH
661:22
651:CH
636:20
626:CH
611:18
601:CH
586:16
576:CH
561:14
551:CH
536:12
526:CH
511:10
501:CH
476:CH
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241:,
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3247:K
3238:a
3235:K
3233:p
3205:0
3183:0
3161:0
3139:0
3117:0
3095:0
3073:0
3051:0
3029:0
3007:0
2985:0
2963:0
2941:0
2740:H
2688:2
2446:x
2444:−
2442:n
2438:D
2436::
2434:C
2417:2
2407:D
2403:C
2399:D
2397::
2395:C
2378:,
2374:,
2351:n
2344:n
2339:x
2337:−
2335:n
2327:x
2323:x
2313:n
2296:x
2287:x
2280:x
2273:x
2269:n
2266:(
2263:x
2261:−
2259:n
2245:n
2238:x
2233:x
2231:−
2229:n
2189:x
2180:x
2174:Δ
2149:Z
2143:E
2138:-
2093:Z
2012:3
2005:–
2000:2
1993:–
1988:2
1981:–
1976:2
1969:–
1964:2
1949:n
1924:D
1912:y
1910:,
1908:x
1889:x
1885:x
1851:x
1847:x
1843:x
1839:x
1808:x
1804:x
1733:n
1715:4
1713:)
1711:2
1704:8
1702:)
1700:2
1696:3
1682:n
1664:9
1662:)
1660:2
1653:5
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383:2
379:3
374:.
346:.
173:e
166:t
159:v
83:(
20:)
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