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Coenzyme Q10

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InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
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InChI=1/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
1555:. The plasma peak can be observed 6–8 hours after oral administration when taken as a pharmacological substance. In some studies, a second plasma peak also was observed at approximately 24 hours after administration, probably due to both enterohepatic recycling and redistribution from the liver to circulation. 1411:
found a 31% lower mortality and increased exercise capacity, with no significant difference in the endpoints of left heart ejection fraction. A 2021 meta-analysis found that coenzyme Q10 was associated with a 31% lower all-cause mortality in HF patients. In a 2023 meta-analysis of older people,
4819: 1623:. Various approaches have been developed to achieve this goal, with many of them producing significantly better results over oil-based softgel capsules in spite of the many attempts to optimize their composition. Examples of such approaches are use of the aqueous dispersion of solid CoQ 4838: 992:). The capacity of this molecule to act as a two-electron carrier (moving between the quinone and quinol form) and a one-electron carrier (moving between the semiquinone and one of these other forms) is central to its role in the electron transport chain due to the 755:
The mitochondrial oxidative phosphorylation process takes place in the inner mitochondrial membrane of eukaryotic cells. This membrane is highly folded into structures called cristae, which increase the surface area available for oxidative phosphorylation.
1255:. However, the role statins play in CoQ deficiency is controversial. Although statins reduce blood levels of CoQ, studies on the effects of muscle levels of CoQ are yet to come. CoQ supplementation also does not reduce side effects of statin medications. 938:
chemical subunits (shown enclosed in brackets in the diagram) in its tail. In natural ubiquinones, there are from six to ten subunits in the tail, with humans having a tail of 10 isoprene units (50 carbon atoms) connected to its benzoquinone "head".
3891: 3832: 3093: 1243:, usually a target for intervention in cardiovascular complications. The "statin" family of cholesterol-reducing medications inhibits HMG-CoA reductase. One possible side effect of statins is decreased production of CoQ 3278: 1341:
is naturally produced by the body and plays a crucial role in cell growth and protection. Despite its significant role in the body, it is not used as a drug for the treatment of any specific disease.
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is widely available as an over-the-counter dietary supplement and is recommended by some healthcare professionals, despite a lack of definitive scientific evidence supporting these recommendations.
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have been explored as a delivery system for various drugs, such as improving the oral bioavailability of drugs with poor absorption characteristics. However, this has not proved successful with CoQ
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Banach M, Serban C, Sahebkar A, Ursoniu S, Rysz J, Muntner P, et al. (January 2015). "Effects of coenzyme Q10 on statin-induced myopathy: a meta-analysis of randomized controlled trials".
5341: 3943: 870:, a group of gram-negative bacteria. The fact that the coenzyme is ubiquitous gives the origin of its other name, ubiquinone. In humans, the most common form of coenzymes Q is coenzyme Q 3516:
Montero R, Sánchez-Alcázar JA, Briones P, Hernández AR, Cordero MD, Trevisson E, et al. (June 2008). "Analysis of coenzyme Q10 in muscle and fibroblasts for the diagnosis of CoQ
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International Journal for Vitamin and Nutrition Research. Internationale Zeitschrift Fur Vitamin- und Ernahrungsforschung. Journal International de Vitaminologie et de Nutrition
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Mathiowitz E, Jacob JS, Jong YS, Carino GP, Chickering DE, Chaturvedi P, et al. (March 1997). "Biologically erodable microspheres as potential oral drug delivery systems".
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International Journal for Vitamin and Nutrition Research. Internationale Zeitschrift Fur Vitamin- und Ernahrungsforschung. Journal International de Vitaminologie et de Nutrition
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molecule that is located in all biological membranes of human body and serves as a component for the synthesis of ATP and is a life-sustaining cofactor for the three complexes (
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Ozawa Y, Mizushima Y, Koyama I, Akimoto M, Yamagata Y, Hayashi H, et al. (April 1986). "Intestinal absorption enhancement of coenzyme Q10 with a lipid microsphere".
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powder insoluble in water. Absorption as a pharmacological substance follows the same process as that of lipids; the uptake mechanism appears to be similar to that of
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cells, primarily in the mitochondria. Ninety-five percent of the human body's energy is generated this way. Organs with the highest energy requirements—such as the
4263:"Comparison of Coenzyme Q10 (Ubiquinone) and Reduced Coenzyme Q10 (Ubiquinol) as Supplement to Prevent Cardiovascular Disease and Reduce Cardiovascular Mortality" 717:(ETC), where it plays a role in oxidative phosphorylation, a process required for the biosynthesis of adenosine triphosphate, the primary energy source of cells. 2587:
Kadian M, Sharma G, Pandita S, Sharma K, Shrivasatava K, Saini N, et al. (2022). "The Impact of Coenzyme Q10 on Neurodegeneration: A Comprehensive Review".
1156:. Q refers to the quinone head and "10" refers to the number of isoprene repeats in the tail. The molecule below has three isoprenoid units and would be called Q 772:(complex I), and succinate ubiquinone reductase (complex II), the fatty acids and branched-chain amino acids oxidation (through flavin-linked dehydrogenases) to 5614: 4852:
Zmitek J, Smidovnik A, Fir M, Prosek M, Zmitek K, Walczak J, et al. (2008). "Relative bioavailability of two forms of a novel water-soluble coenzyme Q10".
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participates in fatty acid and glucose metabolism by transferring electrons generated from the reduction of fatty acids and glucose to electron acceptors;
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Desbats MA, Lunardi G, Doimo M, Trevisson E, Salviati L (January 2015). "Genetic bases and clinical manifestations of coenzyme Q10 (CoQ 10) deficiency".
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Facilitating drug absorption by increasing its solubility in water is a common pharmaceutical strategy and also has been shown to be successful for CoQ
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Bogentoft C, Edlund PO, Olsson B, Widlund L, Westensen K (1991). "Biopharmaceutical aspects of intravenous and oral administration of coenzyme Q10.".
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is metabolized in all tissues, with the metabolites being phosphorylated in cells. CoQ10 is reduced to ubiquinol during or after absorption in the
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Organisms other than humans produce the benzoquinone and isoprene structures from somewhat different source chemicals. For example, the bacteria
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plays a role in this process as an essential cofactor of the ETC located in the inner mitochondrial membrane and serves the following functions:
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substances. Food intake (and the presence of lipids) stimulates bodily biliary excretion of bile acids and greatly enhances absorption of CoQ
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found insufficient evidence to make a conclusion about its use for the prevention of heart disease. A 2016 Cochrane review concluded that CoQ
3650: 1686:. The observed safe level risk assessment method indicated that the evidence of safety is acceptable at intakes up to 1200 mg per day. 838: 3227:
Shindo Y, Witt E, Han D, Epstein W, Packer L (January 1994). "Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin".
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Joshi SS, Sawant SV, Shedge A, Halpner AD (January 2003). "Comparative bioavailability of two novel coenzyme Q10 preparations in humans".
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Arenas-Jal M, Suñé-Negre JM, García-Montoya E (March 2020). "Coenzyme Q10 supplementation: Efficacy, safety, and formulation challenges".
2406: 1678:, and headaches. Some adverse effects, largely gastrointestinal, are reported with intakes. Doses of 100–300 mg per day may induce 1337:
is commonly used as a dietary supplement with the intent to prevent or improve disease conditions, such as cardiovascular disorders. CoQ
6386: 5467: 5386: 4817:, Westesen K, Siekmann B, "Particles with modified physicochemical properties, their preparation and uses", published 2001 4520:
Tomono Y, Hasegawa J, Seki T, Motegi K, Morishita N (October 1986). "Pharmacokinetic study of deuterium-labeled coenzyme Q10 in man".
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O=C1/C(=C(\C(=O)C(\OC)=C1\OC)C)C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C
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Aberg F, Appelkvist EL, Dallner G, Ernster L (June 1992). "Distribution and redox state of ubiquinones in rat and human tissues".
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Okamoto T, Matsuya T, Fukunaga Y, Kishi T, Yamagami T (1989). "Human serum ubiquinol-10 levels and relationship to serum lipids".
1317:. Most organisms share the common 4-hydroxybenzoate intermediate, yet again uses different steps to arrive at the "Q" structure. 6356: 1369: 4603:"Bioavailability and Sustained Plasma Concentrations of CoQ10 in Healthy Volunteers by a Novel Oral Timed-Release Preparation" 5844: 5710: 5624: 5454: 5442: 5391: 3621:"Effect of Coenzyme Q10 on statin-associated myalgia and adherence to statin therapy: A systematic review and meta-analysis" 2499: 2297:
quinone found in all animal tissues. In 1958, its full chemical structure was reported. Ubiquinone was later called either
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produced by the human body. It can also be obtained from dietary sources, such as meat, fish, seed oils, vegetables, and
569: 5450: 4836:, Ohashi H, Takami T, Koyama N, Kogure Y, Ida K, "Aqueous solution containing ubidecarenone", published 1984 4090:
Al Saadi T, Assaf Y, Farwati M, Turkmani K, Al-Mouakeh A, Shebli B, et al. (Cochrane Heart Group) (February 2021).
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reducing statin-associated muscle symptoms, including muscle pain, muscle weakness, muscle cramps and muscle tiredness.
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has been found to have highly increased bioavailability and also is used in pharmaceutical and food industries for CoQ
319: 6422: 6122: 1086:, these measurements reflect dietary intake rather than tissue status. Currently, most clinical centers measure CoQ 2689:
Pradhan N, Singh C, Singh A (November 2021). "Coenzyme Q10 a mitochondrial restorer for various brain disorders".
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due to its participation to the mitochondrial electron transport chain. In 1966, a study reported that reduced CoQ
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had no effect on statin myopathy. A 2018 meta-analysis concluded that there was preliminary evidence for oral CoQ
661: 2789:"Clinical Evidence for Q10 Coenzyme Supplementation in Heart Failure: From Energetics to Functional Improvement" 2285:
membranes of beef heart, with research showing that it transported electrons within mitochondria. It was called
6337: 6332: 5997: 5546: 5506: 5381: 4705:"Preparation and characterization of novel coenzyme Q10 nanoparticles engineered from microemulsion precursors" 4411:
Bhagavan HN, Chopra RK (May 2006). "Coenzyme Q10: absorption, tissue uptake, metabolism and pharmacokinetics".
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and protecting cells against oxidative stress, inhibiting the oxidation of proteins, DNA, and use of vitamin E.
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Crane FL, Hatefi Y, Lester RL, Widmer C (July 1957). "Isolation of a quinone from beef heart mitochondria".
2498:. National Center for Complementary and Integrative Health, US National Institutes of Health. January 2019. 2281:, but later deemed to be quinone found in many animal tissues. In 1957, the same compound was isolated from 859: 788: 635: 241: 6447: 5910: 5752: 5530: 5479: 5446: 5061:
Pravst I, Zmitek K, Zmitek J (April 2010). "Coenzyme Q10 contents in foods and fortification strategies".
1604: 1098:, and blood mononuclear cells. Culture fibroblasts can be used also to evaluate the rate of endogenous CoQ 985: 665: 672:
consists of a benzoquinone moiety and an isoprenoid side chain, with the "10" referring to the number of
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electron transport in the mitochondrial ETC, by shuttling electrons from mitochondrial complexes like
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was used to investigate pharmacokinetics in humans to determine an elimination half-time of 33 hours.
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supplements may be reduced due to the lipophilic nature of its molecule and large molecular weight.
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Kagan D, Madhavi D (2010). "A Study on the Bioavailability of a Novel Sustained-Release Coenzyme Q
4552:"Bioavailability of Coenzyme Q10: An Overview of the Absorption Process and Subsequent Metabolism" 3837: 6432: 6351: 6152: 6024: 5566: 5305: 5086: 5036: 4952: 4877: 4685: 4436: 3620: 3601: 1760:
and dietary intake were published in 2010. Besides the endogenous synthesis within organisms, CoQ
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Justine Perrin R, Rousset-Rouvière C, Garaix F, Cano A, Conrath J, Boyer O, et al. (2020).
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Pyo Y, Oh H (2011). "Ubiquinone contents in Korean fermented foods and average daily intakes".
4141:"Efficacy of coenzyme Q10 in patients with cardiac failure: a meta-analysis of clinical trials" 3471:
Trevisson E, DiMauro S, Navas P, Salviati L (October 2011). "Coenzyme Q deficiency in muscle".
2726:"Cellular Consequences of Coenzyme Q10 Deficiency in Neurodegeneration of the Retina and Brain" 2402: 1662:
supplementation is well tolerated. The most common side effects are gastrointestinal symptoms (
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Mellors A, Tappel AL (July 1966). "Quinones and quinols as inhibitors of lipid peroxidation".
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in muscle. Evidence does not support that supplementation improves side effects from statins.
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Di Lorenzo A, Iannuzzo G, Parlato A, Cuomo G, Testa C, Coppola M, et al. (April 2020).
2747: 2737: 2698: 2644: 2634: 2596: 2544: 2534: 2405:. Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2018. 1733: 1548: 927: 881: 593: 523: 473: 413: 78: 5131:
Weber C, Bysted A, Hłlmer G (1997). "The coenzyme Q10 content of the average Danish diet".
1396:. A 2021 Cochrane review found "no convincing evidence to support or refute" the use of CoQ 996:
that can only accept one electron at a time, and as a free radical–scavenging antioxidant.
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Khan MS, Khan F, Fonarow GC, Sreenivasan J, Greene SJ, Khan SU, et al. (June 2021).
3342:"COQ6 mutations in human patients produce nephrotic syndrome with sensorineural deafness" 139: 5319: 5180: 5023: 5006: 4665: 4393: This article incorporates text from this source, which is available under the 4289: 4262: 4203: 4187: This article incorporates text from this source, which is available under the 3395:
mutation in patients with nephrotic syndrome, sensorineural deafness, and optic atrophy"
3027: This article incorporates text from this source, which is available under the 2964: This article incorporates text from this source, which is available under the 2944: 2917: 2901: This article incorporates text from this source, which is available under the 2835: This article incorporates text from this source, which is available under the 2772: This article incorporates text from this source, which is available under the 2669: This article incorporates text from this source, which is available under the 2569: This article incorporates text from this source, which is available under the 1634:, formulations based on various solubilising agents, such as hydrogenated lecithin, and 1174:
In its pure state, it is an orange-colored lipophile powder, and has no taste nor odor.
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Bentinger M, Tekle M, Dallner G (May 2010). "Coenzyme Q--biosynthesis and functions".
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is shown below. The various kinds of coenzyme Q may be distinguished by the number of
6411: 5987: 5940: 5892: 5223: 3205: 3142: 3125: 2195: 1828: 1818: 1793: 1718: 1694: 1639: 1497: 1404: 1313:, however, derives the former from either chorismate or tyrosine and the latter from 1309: 1191: 725: 692: 527: 462: 234: 5090: 4970:
Hathcock JN, Shao A (August 2006). "Risk assessment for coenzyme Q10 (Ubiquinone)".
4956: 4440: 3994:"Co-enzyme Q10 supplementation for the primary prevention of cardiovascular disease" 3098: 1748:
is not recommended in people taking warfarin due to the increased risk of clotting.
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PDQ Integrative, Alternative, and Complementary Therapies Editorial Board (2002).
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bioavailability when it is taken as a dietary supplement. Bioavailability of CoQ
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is absorbed from the small intestine and is best absorbed if taken with a meal.
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Ochiai A, Itagaki S, Kurokawa T, Kobayashi M, Hirano T, Iseki K (August 2007).
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Inherited Neuromuscular Diseases: Translation from Pathomechanisms to Therapies
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Heeringa SF, Chernin G, Chaki M, Zhou W, Sloan AJ, Ji Z, et al. (2011).
1744:, which competes with and counteracts warfarin's anticoagulation effects. CoQ 1713:
taken as a pharmacological substance has potential to inhibit the effects of
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Wolf DE (1958). "Coenzyme Q. I. structure studies on the coenzyme Q group".
4364: 3795: 2322: 2021: 1808: 1741: 1631: 1536: 1461: 1457: 1103: 989: 943: 784: 729: 531: 5301: 5231: 5196: 5082: 5032: 4991: 4948: 4939: 4922: 4873: 4773: 4738: 4638: 4587: 4506: 4432: 4382: 4333: 4298: 4235: 4176: 4125: 4076: 4043:"Blood pressure lowering efficacy of coenzyme Q10 for primary hypertension" 4027: 3978: 3869: 3813: 3768: 3693: 3646: 3597: 3551: 3502: 3428: 3375: 3326: 3069: 3016: 2997: 2953: 2934: 2890: 2824: 2761: 2710: 2658: 2639: 2558: 2464: 2277:
was isolated from the lining of a horse's gut, a compound initially called
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ubiquinone had evidence of a cardiovascular effect, but ubiquinol did not.
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is not regulated, and different batches and brands may vary significantly.
1364:(FDA) for the treatment of any medical condition. However, it is sold as a 1024:
levels also may be affected by other genetic defects (such as mutations of
5144: 4800: 4681: 4568: 4533: 3248: 3213: 3178: 3151: 1460:, another lipid-soluble nutrient. This process in the human body involves 31: 6280: 6189: 5408: 3542: 2871: 2742: 2539: 2238:
has been determined at 3–6 mg per day, derived primarily from meat.
2203: 2064: 2031: 1955: 1944: 1721: 1679: 1248: 1206: 1195: 1067: 935: 749: 684: 673: 5258: 3942:. UK: National Institute for Health and Care Excellence. 28 March 2017. 3493: 1165: 1012:, and increased use by the body. Biosynthesis is the major source of CoQ 6305: 6088: 6032: 5744: 5293: 4619: 4522:
International Journal of Clinical Pharmacology, Therapy, and Toxicology
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Flowers N, Hartley L, Todkill D, Stranges S, Rees K (4 December 2014).
3804: 3588: 3571: 3410: 3271:"Improving the bioavailability of coenzyme q10 from theory to practice" 3126:"Biochemical, physiological and medical aspects of ubiquinone function" 2805: 2219: 2109: 2084: 2054: 1934: 1628: 1481: 1453: 1295: 1182:
Biosynthesis occurs in most human tissue. There are three major steps:
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Sharma A, Fonarow GC, Butler J, Ezekowitz JA, Felker GM (April 2016).
4923:"Coenzyme Q10: a therapy for hypertension and statin-induced myalgia?" 4865: 4497: 4219: 2916:
Mantle D, Millichap L, Castro-Marrero J, Hargreaves IP (August 2023).
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Except where otherwise noted, data are given for materials in their
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This family of fat-soluble substances is present in all respiring
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antioxidant activity as a lipid-soluble antioxidant together with
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Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease
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International Journal of Clinical Pharmacology and Therapeutics
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Manzar H, Abdulhussein D, Yap TE, Cordeiro MF (December 2020).
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disease, during pregnancy or breastfeeding, or in the elderly.
3044:"Occurrence, biosynthesis and function of isoprenoid quinones" 1576:
as a constituent of food, such as nuts or meat, from which CoQ
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Qu H, Guo M, Chai H, Wang WT, Gao ZY, Shi DZ (October 2018).
2325:– synthetic analog with reduced oxidant generating properties 899: 611: 1603:, although reports have differed widely. The use of aqueous 1164: 1020:, and mutations in any of them can cause CoQ deficiency. CoQ 650:
is found in many organisms, including animals and bacteria.
324: 96: 5007:"Coenzyme Q10 and Heart Failure: A State-of-the-Art Review" 2331:– synthetic analog with improved mitochondrial permeability 1056:
biosynthetic process). Some of these, such as mutations in
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may interfere with warfarin's actions by interacting with
1236:, indicating multiple sites of synthesis in animal cells. 2855:"Disorders of Human Coenzyme Q10 Metabolism: An Overview" 2234:
In the developed world, the estimated daily intake of CoQ
1152:. The most common coenzyme Q in human mitochondria is CoQ 1062:, can lead to serious diseases such as steroid-resistant 896: 608: 3083: 3081: 3079: 2523:"Coenzyme Q10 Metabolism: A Review of Unresolved Issues" 691:, and its use as a supplement is not associated with or 2521:
Mantle D, Lopez-Lluch G, Hargreaves IP (January 2023).
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Sood B, Preeti Patel P, Keenaghan M (30 January 2024).
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as a quinone. The Q-275/substance SA was later renamed
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in fed condition is higher than in fasting conditions.
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2--5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
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Comprehensive Reviews in Food Science and Food Safety
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Hargreaves I, Heaton RA, Mantle D (September 2020).
2241:
South Koreans have an estimated average daily CoQ (Q
1407:
of people with heart failure 30–100 mg/d of CoQ
905: 679:
Although a ubiquitous molecule in human tissues, CoQ
617: 102: 6374: 6325: 6145: 6080: 6023: 5901: 5743: 5736: 5668: 5559: 5543: 5515: 5496: 5477: 5432: 5423: 5364: 3674:
Biochemical and Biophysical Research Communications
3048:
Biochimica et Biophysica Acta (BBA) - Bioenergetics
2249:) intake of 11.6 mg/d, derived primarily from 2190:
Vegetable oils, meat and fish are quite rich in CoQ
1736:, a measure of blood clotting. The structure of CoQ 902: 634:also known as ubiquinone, is a naturally occurring 614: 99: 1693:supplementation is not recommended in people with 1580:is normally absorbed, there is a concern about CoQ 803:by modulating the expression of genes involved in 61:In general: Ubiquinone, coenzyme Q, CoQ, vitamin Q 4601:Martucci A, Reurean-Pintilei D, Manole A (2019). 1004:There are two major pathways of deficiency of CoQ 5681:Electron-transferring-flavoprotein dehydrogenase 3105:. US National Library of Medicine. 30 March 2024 2214:. Most fruit and berries are poor sources of CoQ 1611:in pure water also reveals only a minor effect. 1427:medications, a 2015 meta-analysis found that CoQ 1419:has been used to treat purported muscle-related 1052:, genes that are not directly related to the CoQ 934:chemical group and "10" refers to the number of 752:membranes to regulate pH in lysosome functions. 467:48–52 °C (118–126 °F; 321–325 K) 286: 5586:Complex III/Coenzyme Q - cytochrome c reductase 5162: 5160: 5158: 5156: 5154: 5056: 5054: 5052: 5050: 4916: 4914: 4406: 4404: 3619:Kennedy C, Köller Y, Surkova E (1 April 2020). 3565: 3563: 3561: 3466: 3464: 3300: 3298: 3296: 2848: 2846: 2623:"Coenzyme Q10 and Immune Function: An Overview" 2621:Mantle D, Heaton RA, Hargreaves IP (May 2021). 2459:. StatPearls, US National Library of Medicine. 1247:, which may be connected to the development of 138: 5063:Critical Reviews in Food Science and Nutrition 3264: 3262: 3260: 3258: 2684: 2682: 2680: 2616: 2614: 2612: 2610: 830:needs attention from an expert in biochemistry 6123: 5711: 5335: 4456:Biomedical and clinical aspects of coenzyme Q 3881: 3879: 2582: 2580: 1128:in the blood it is unclear if they reduce CoQ 8: 4921:Wyman M, Leonard M, Morledge T (July 2010). 2918:"Primary Coenzyme Q10 Deficiency: An Update" 4261:Fladerer JP, Grollitsch S (December 2023). 4096:The Cochrane Database of Systematic Reviews 4047:The Cochrane Database of Systematic Reviews 3998:The Cochrane Database of Systematic Reviews 3743:"Ubiquinone biosynthesis in microorganisms" 2527:International Journal of Molecular Sciences 6130: 6116: 6108: 5740: 5718: 5704: 5696: 5556: 5429: 5342: 5328: 5320: 3576:American Journal of Health-System Pharmacy 2222:, which have a relatively high oil and CoQ 339: 244: 222: 20: 5167:Morton RA (December 1958). "Ubiquinone". 5022: 4938: 4728: 4628: 4618: 4577: 4567: 4545: 4543: 4496: 4486: 4372: 4353:Journal of the American Heart Association 4288: 4278: 4166: 4156: 4115: 4066: 4017: 3862:Coenzyme Q10: Health Professional Version 3803: 3758: 3636: 3587: 3541: 3492: 3418: 3365: 3141: 3059: 3006: 2996: 2943: 2933: 2880: 2870: 2814: 2804: 2751: 2741: 2648: 2638: 2548: 2538: 1102:biosynthesis, by measuring the uptake of 306: 5247:Journal of the American Chemical Society 5106:Journal of Food Composition and Analysis 4703:Hsu CH, Cui Z, Mumper RJ, Jay M (2003). 3229:The Journal of Investigative Dermatology 1770: 1547:Some reports have been published on the 1524:, and redistributed in the blood within 4316:(Systematic Review and Meta-Analysis). 3915:U.S. Dept. of Health and Human Services 3194:Archives of Biochemistry and Biophysics 2490: 2488: 2486: 2450: 2448: 2446: 2444: 2341: 2202:than animal tissues. Among vegetables, 1239:An important enzyme in this pathway is 695:for any health or anti-disease effect. 395: 360: 335: 4972:Regulatory Toxicology and Pharmacology 4041:Ho MJ, Li EC, Wright JM (March 2016). 2442: 2440: 2438: 2436: 2434: 2432: 2430: 2428: 2426: 2424: 2397: 2395: 2393: 2391: 2389: 2387: 2385: 2383: 2381: 2379: 2377: 2375: 2373: 2371: 2369: 2367: 2365: 1764:also is supplied by various foods. CoQ 841:may be able to help recruit an expert. 235: 3707:Espinós C, Felipo V, Palau F (2009). 3653:from the original on 28 December 2022 3638:10.1016/j.atherosclerosis.2020.03.006 2363: 2361: 2359: 2357: 2355: 2353: 2351: 2349: 2347: 2345: 1768:concentrations in various foods are: 1756:Detailed reviews on occurrence of CoQ 1642:; among the latter, the complex with 1484:formation required for absorption of 740:) of the ETC in the mitochondria. CoQ 367:Key: ACTIUHUUMQJHFO-UPTCCGCDSA-N 202: 182: 7: 4927:Cleveland Clinic Journal of Medicine 4854:Annals of Nutrition & Metabolism 3946:from the original on 10 October 2019 3269:Žmitek J, ŽMitek K, Pravs I (2008). 3042:Nowicka B, Kruk J (September 2010). 1400:for the treatment of heart failure. 1016:. Biosynthesis requires at least 15 713:is a component of the mitochondrial 500: 16:Biochemical cofactor and antioxidant 5024:10.1161/CIRCHEARTFAILURE.115.002639 4242:from the original on 2 January 2023 2691:Naunyn Schmiedebergs Arch Pharmacol 2471:from the original on 2 October 2023 1224:The initial two reactions occur in 377:Key: ACTIUHUUMQJHFO-UPTCCGCDBK 277: 261: 5572:Complex II/Succinate dehydrogenase 5468:Pyruvate dehydrogenase phosphatase 3760:10.1111/j.1574-6968.2001.tb10831.x 3281:from the original on 23 April 2024 2409:from the original on 15 March 2024 14: 4208:European Journal of Heart Failure 3534:10.1016/j.clinbiochem.2008.03.007 3449:from the original on 6 April 2024 3346:Journal of Clinical Investigation 3124:Ernster L, Dallner G (May 1995). 2979:Barcelos IP, Haas RH (May 2019). 2502:from the original on 4 April 2024 1558:Deuterium-labeled crystalline CoQ 766:nicotinamide adenine dinucleotide 4458:. Vol. 6. pp. 215–224. 4388: 4182: 4092:"Coenzyme Q10 for heart failure" 3890: This article incorporates 3885: 3831: This article incorporates 3826: 3092: This article incorporates 3087: 3022: 2959: 2896: 2830: 2767: 2664: 2564: 880: 819: 774:ubiquinol–cytochrome-c reductase 592: 547: 425: 77: 30: 5596:Complex IV/Cytochrome c oxidase 3741:Meganathan R (September 2001). 1654:Adverse effects and precautions 1124:Although statins may reduce CoQ 969:states of CoQ: fully oxidized ( 744:has a role in the transport of 676:chemical subunits in its tail. 543:(at 25 °C , 100 kPa). 5443:Pyruvate dehydrogenase complex 4108:10.1002/14651858.CD008684.pub3 4059:10.1002/14651858.CD007435.pub3 4010:10.1002/14651858.CD010405.pub2 3570:Tan JT, Barry AR (June 2017). 2273:In 1950, a small amount of CoQ 2198:are much poorer sources of CoQ 1370:regulations as medicinal drugs 664:, aiding in the production of 431: 419: 1: 5464:Pyruvate dehydrogenase kinase 5212:Biochimica et Biophysica Acta 3911:National Institutes of Health 2261:Cooking by frying reduces CoQ 2257:Effect of heat and processing 1732:enzymes thereby reducing the 1528:. Its elimination occurs via 1140:The oxidized structure of CoQ 930:, in which "Q" refers to the 776:(complex III) of the ETC: CoQ 5567:Complex I/NADH dehydrogenase 5224:10.1016/0006-3002(57)90457-2 4550:Mantle D, Dybring A (2020). 4326:10.1016/j.mayocp.2014.08.021 4145:BMC Cardiovascular Disorders 3713:. Springer. pp. 122ff. 3485:10.1097/WCO.0b013e32834ab528 3473:Current Opinion in Neurology 3241:10.1111/1523-1747.ep12371744 3206:10.1016/0003-9861(92)90511-T 3143:10.1016/0925-4439(95)00028-3 3061:10.1016/j.bbabio.2010.06.007 2589:Current Pharmacology Reports 1572:In contrast to intake of CoQ 1362:Food and Drug Administration 1360:is not approved by the U.S. 4984:10.1016/j.yrtph.2006.05.006 3965:Hojerová J (May 2000). "". 1705:Potential drug interactions 1220:of the above two structures 6469: 5387:Oxoglutarate dehydrogenase 5118:10.1016/j.jfca.2011.03.018 5011:Circulation: Heart Failure 4899:-β-Cyclodextrin Complex". 4280:10.1007/s11886-023-01992-6 4267:Current Cardiology Reports 4139:Lei L, Liu Y (July 2017). 3967:Ceska a Slovenska Farmacie 3686:10.1016/j.bbrc.2010.02.147 3275:Agro Food Industry Hi-Tech 2703:10.1007/s00210-021-02161-8 2601:10.1007/s40495-021-00273-6 1592:Reduction of particle size 1352:Regulation and composition 1303:and the latter from a non- 702: 5552:oxidative phosphorylation 5075:10.1080/10408390902773037 4425:10.1080/10715760600617843 4158:10.1186/s12872-017-0628-9 3907:National Cancer Institute 3847:National Cancer Institute 3747:FEMS Microbiology Letters 3319:10.1007/s10545-014-9749-9 2103: 2050: 1985: 1928: 1901: 1874: 1847: 1792: 1780: 1776:levels in selected foods 1307:source. The common yeast 1299:produces the former from 662:oxidative phosphorylation 537: 509: 483: 406: 386: 351: 122: 64:This form: ubidecarenone, 55: 43: 38: 29: 6338:Butylated hydroxytoluene 6333:Butylated hydroxyanisole 5547:electron transport chain 5507:Methylmalonyl-CoA mutase 5382:Isocitrate dehydrogenase 4488:10.1248/yakushi.127.1251 2218:, with the exception of 1368:not subject to the same 1090:levels in cultured skin 839:WikiProject Biochemistry 715:electron transport chain 689:recommended intake level 5488:Glutamate dehydrogenase 5399:Succinate dehydrogenase 5392:Succinyl CoA synthetase 4365:10.1161/JAHA.118.009835 4314:Mayo Clinic Proceedings 3896:White J (14 May 2014). 3796:10.1111/1541-4337.12539 3520:deficiency syndromes". 2210:are good sources of CoQ 1258:Genes involved include 789:reactive oxygen species 457:yellow or orange solid 5531:Aspartate transaminase 4940:10.3949/ccjm.77a.09078 4789:Arzneimittel-Forschung 3892:public domain material 3833:public domain material 3094:public domain material 2998:10.3390/biology8020028 2935:10.3390/antiox12081652 2640:10.3390/antiox10050759 1788:concentration (mg/kg) 1752:Dietary concentrations 1740:is similar to that of 1607:of finely powdered CoQ 1452:in the pure form is a 1169: 666:adenosine triphosphate 4569:10.3390/antiox9050386 4413:Free Radical Research 3522:Clinical Biochemistry 1230:endoplasmic reticulum 1168: 958:—have the highest CoQ 6428:Cellular respiration 5526:Pyruvate carboxylase 5414:Malate dehydrogenase 4901:Integrative Medicine 2872:10.3390/ijms21186695 2743:10.3390/ijms21239299 2540:10.3390/ijms24032585 2329:Mitoquinone mesylate 1668:appetite suppression 1520:. It is absorbed by 1500:concentration of CoQ 1476:, which facilitates 994:iron–sulfur clusters 984:quinone), and fully 919:) or ubiquinone-10. 866:in animals and many 770:ubiquinone reductase 699:Biological functions 687:and does not have a 636:biochemical cofactor 45:Preferred IUPAC name 5676:Alternative oxidase 5480:α-ketoglutaric acid 5259:10.1021/ja01550a096 5181:1958Natur.182.1764M 5175:(4652): 1764–1767. 4666:1997Natur.386..410M 3307:J Inherit Metab Dis 2265:content by 14–32%. 1777: 1658:Generally, oral CoQ 1325:Although neither a 1136:Chemical properties 1082:may be measured in 1066:with sensorineural 1008:in humans: reduced 799:also may influence 644:dietary supplements 474:Solubility in water 449: g·mol 26: 6352:1,2-Diaminopropane 6153:6-Hydroxymelatonin 5294:10.1007/BF02531617 4620:10.3390/nu11030527 3589:10.2146/ajhp160714 3411:10.1002/jmd2.12068 2806:10.3390/jcm9051266 1771: 1470:pancreatic enzymes 1366:dietary supplement 1331:essential nutrient 1321:Dietary supplement 1209:side chain (using 1170: 1148:subunits in their 1064:nephrotic syndrome 638:(coenzyme) and an 570:Infobox references 510:Related compounds 21: 6423:1,4-Benzoquinones 6405: 6404: 6326:Fuel antioxidants 6217: 6168:Alpha-lipoic acid 6161: 6146:Food antioxidants 6105: 6104: 6076: 6075: 5693: 5692: 5689: 5688: 5539: 5538: 5355:Citric acid cycle 5189:10.1038/1821764a0 4866:10.1159/000129661 4709:AAPS PharmSciTech 4660:(6623): 410–414. 4273:(12): 1759–1767. 4220:10.1002/ejhf.2278 3720:978-90-481-2812-9 2981:"CoQ10 and Aging" 2697:(11): 2197–2222. 2309:was an effective 2188: 2187: 1392:had no effect on 1344:Nevertheless, CoQ 1327:prescription drug 1241:HMG-CoA reductase 1200:4-hydroxybenzoate 1190:structure (using 1026:mitochondrial DNA 874:, also called CoQ 858:Coenzymes Q is a 856: 855: 683:is not a dietary 578:Chemical compound 576: 575: 320:CompTox Dashboard 164:Interactive image 6460: 6250:-Acetylserotonin 6215: 6159: 6132: 6125: 6118: 6109: 5741: 5720: 5713: 5706: 5697: 5557: 5518:oxaloacetic acid 5430: 5372:Citrate synthase 5344: 5337: 5330: 5321: 5314: 5313: 5277: 5271: 5270: 5242: 5236: 5235: 5207: 5201: 5200: 5164: 5149: 5148: 5128: 5122: 5121: 5112:(8): 1123–1129. 5101: 5095: 5094: 5058: 5045: 5044: 5026: 5002: 4996: 4995: 4967: 4961: 4960: 4942: 4918: 4909: 4908: 4892: 4886: 4885: 4849: 4843: 4842: 4841: 4837: 4830: 4824: 4823: 4822: 4818: 4811: 4805: 4804: 4784: 4778: 4777: 4766:10.5414/CPP41042 4749: 4743: 4742: 4732: 4721:10.1208/pt040332 4700: 4694: 4693: 4674:10.1038/386410a0 4649: 4643: 4642: 4632: 4622: 4598: 4592: 4591: 4581: 4571: 4547: 4538: 4537: 4517: 4511: 4510: 4500: 4490: 4481:(8): 1251–1254. 4466: 4460: 4459: 4451: 4445: 4444: 4408: 4399: 4392: 4386: 4376: 4344: 4338: 4337: 4309: 4303: 4302: 4292: 4282: 4258: 4252: 4251: 4249: 4247: 4214:(9): 1468–1476. 4199: 4193: 4186: 4180: 4170: 4160: 4136: 4130: 4129: 4119: 4087: 4081: 4080: 4070: 4038: 4032: 4031: 4021: 4004:(12): CD010405. 3989: 3983: 3982: 3962: 3956: 3955: 3953: 3951: 3932: 3926: 3925: 3923: 3921: 3889: 3888: 3883: 3874: 3873: 3857: 3851: 3850: 3830: 3829: 3824: 3818: 3817: 3807: 3779: 3773: 3772: 3762: 3738: 3732: 3731: 3729: 3727: 3704: 3698: 3697: 3669: 3663: 3662: 3660: 3658: 3640: 3616: 3610: 3609: 3591: 3567: 3556: 3555: 3545: 3513: 3507: 3506: 3496: 3468: 3459: 3458: 3456: 3454: 3439: 3433: 3432: 3422: 3386: 3380: 3379: 3369: 3358:10.1172/JCI45693 3352:(5): 2013–2024. 3337: 3331: 3330: 3302: 3291: 3290: 3288: 3286: 3266: 3253: 3252: 3224: 3218: 3217: 3189: 3183: 3182: 3162: 3156: 3155: 3145: 3121: 3115: 3114: 3112: 3110: 3091: 3090: 3085: 3074: 3073: 3063: 3054:(9): 1587–1605. 3039: 3033: 3026: 3020: 3010: 3000: 2976: 2970: 2963: 2957: 2947: 2937: 2913: 2907: 2900: 2894: 2884: 2874: 2850: 2841: 2834: 2828: 2818: 2808: 2784: 2778: 2771: 2765: 2755: 2745: 2721: 2715: 2714: 2686: 2675: 2668: 2662: 2652: 2642: 2618: 2605: 2604: 2584: 2575: 2568: 2562: 2552: 2542: 2518: 2512: 2511: 2509: 2507: 2492: 2481: 2480: 2478: 2476: 2452: 2419: 2418: 2416: 2414: 2399: 1778: 1650:-fortification. 1615:Water-solubility 1549:pharmacokinetics 1543:Pharmacokinetics 1205:Creation of the 1186:Creation of the 1114:-hydroxybenzoate 965:There are three 962:concentrations. 928:1,4-benzoquinone 918: 917: 914: 913: 910: 907: 904: 901: 898: 895: 892: 889: 886: 851: 848: 842: 823: 822: 815: 657:plays a role in 630: 629: 626: 625: 622: 619: 616: 613: 610: 607: 604: 601: 598: 560: 554: 551: 550: 524:1,4-Benzoquinone 504: 448: 433: 427: 421: 414:Chemical formula 344: 343: 328: 326: 310: 290: 279: 265: 248: 237: 226: 206: 186: 166: 142: 115: 114: 111: 110: 107: 104: 101: 98: 95: 92: 89: 86: 83: 34: 27: 6468: 6467: 6463: 6462: 6461: 6459: 6458: 6457: 6408: 6407: 6406: 6401: 6370: 6366:Ethylenediamine 6357:2,4-Dimethyl-6- 6321: 6241:-Acetylcysteine 6141: 6136: 6106: 6101: 6072: 6019: 6014: 6006: 5897: 5888: 5880: 5864: 5850: 5840: 5832: 5824: 5814: 5804: 5794: 5772: 5758: 5732: 5724: 5694: 5685: 5664: 5606: 5580: 5550: 5545: 5535: 5511: 5492: 5473: 5419: 5360: 5348: 5318: 5317: 5279: 5278: 5274: 5244: 5243: 5239: 5209: 5208: 5204: 5166: 5165: 5152: 5130: 5129: 5125: 5103: 5102: 5098: 5060: 5059: 5048: 5004: 5003: 4999: 4969: 4968: 4964: 4920: 4919: 4912: 4898: 4894: 4893: 4889: 4851: 4850: 4846: 4839: 4832: 4831: 4827: 4820: 4813: 4812: 4808: 4786: 4785: 4781: 4751: 4750: 4746: 4702: 4701: 4697: 4651: 4650: 4646: 4600: 4599: 4595: 4549: 4548: 4541: 4528:(10): 536–541. 4519: 4518: 4514: 4475:Yakugaku Zasshi 4468: 4467: 4463: 4453: 4452: 4448: 4410: 4409: 4402: 4359:(19): e009835. 4346: 4345: 4341: 4311: 4310: 4306: 4260: 4259: 4255: 4245: 4243: 4201: 4200: 4196: 4138: 4137: 4133: 4102:(2): CD008684. 4089: 4088: 4084: 4053:(3): CD007435. 4040: 4039: 4035: 3991: 3990: 3986: 3964: 3963: 3959: 3949: 3947: 3934: 3933: 3929: 3919: 3917: 3902: 3895: 3886: 3884: 3877: 3859: 3858: 3854: 3842: 3836: 3827: 3825: 3821: 3781: 3780: 3776: 3740: 3739: 3735: 3725: 3723: 3721: 3706: 3705: 3701: 3671: 3670: 3666: 3656: 3654: 3625:Atherosclerosis 3618: 3617: 3613: 3582:(11): 786–793. 3569: 3568: 3559: 3519: 3515: 3514: 3510: 3470: 3469: 3462: 3452: 3450: 3441: 3440: 3436: 3388: 3387: 3383: 3339: 3338: 3334: 3304: 3303: 3294: 3284: 3282: 3268: 3267: 3256: 3226: 3225: 3221: 3191: 3190: 3186: 3164: 3163: 3159: 3123: 3122: 3118: 3108: 3106: 3099:"Ubidecarenone" 3097: 3088: 3086: 3077: 3041: 3040: 3036: 2978: 2977: 2973: 2915: 2914: 2910: 2852: 2851: 2844: 2786: 2785: 2781: 2723: 2722: 2718: 2688: 2687: 2678: 2620: 2619: 2608: 2586: 2585: 2578: 2520: 2519: 2515: 2505: 2503: 2494: 2493: 2484: 2474: 2472: 2454: 2453: 2422: 2412: 2410: 2401: 2400: 2343: 2338: 2319: 2308: 2276: 2271: 2264: 2259: 2248: 2244: 2237: 2232: 2225: 2217: 2213: 2201: 2193: 2095:Chinese cabbage 1787: 1775: 1767: 1763: 1759: 1754: 1747: 1739: 1730:cytochrome p450 1727: 1717:as well as the 1712: 1707: 1692: 1661: 1656: 1649: 1626: 1622: 1617: 1610: 1602: 1594: 1587: 1583: 1579: 1575: 1570: 1568:Bioavailability 1561: 1554: 1545: 1518:small intestine 1515: 1510: 1503: 1495: 1492:. Exogenous CoQ 1491: 1466:small intestine 1451: 1446: 1441: 1434: 1430: 1418: 1410: 1399: 1391: 1386:Cochrane review 1382: 1375: 1359: 1354: 1347: 1340: 1336: 1323: 1246: 1216:The joining or 1180: 1159: 1155: 1143: 1138: 1131: 1127: 1122: 1101: 1089: 1081: 1076: 1055: 1023: 1015: 1007: 1002: 961: 925: 883: 879: 877: 873: 862:family that is 852: 846: 843: 837: 824: 820: 813: 801:immune response 798: 779: 759: 743: 723: 712: 707: 701: 682: 671: 656: 649: 595: 591: 589: 585: 579: 572: 567: 566: 565:  ?) 556: 552: 548: 544: 530: 526: 520: 493: 476: 446: 436: 430: 424: 416: 402: 399: 394: 393: 382: 379: 378: 375: 369: 368: 365: 359: 358: 347: 329: 322: 313: 293: 280: 268: 229: 209: 189: 169: 156: 145: 132: 118: 117: 80: 76: 75: 71: 51: 50: 25: 17: 12: 11: 5: 6466: 6464: 6456: 6455: 6450: 6445: 6443:Meroterpenoids 6440: 6435: 6430: 6425: 6420: 6410: 6409: 6403: 6402: 6400: 6399: 6394: 6389: 6384: 6378: 6376: 6372: 6371: 6369: 6368: 6363: 6354: 6349: 6340: 6335: 6329: 6327: 6323: 6322: 6320: 6319: 6314: 6308: 6303: 6293: 6283: 6278: 6273: 6268: 6263: 6258: 6253: 6244: 6235: 6230: 6225: 6220: 6212: 6210:Hydroxytyrosol 6207: 6202: 6197: 6192: 6187: 6177: 6171: 6165: 6155: 6149: 6147: 6143: 6142: 6137: 6135: 6134: 6127: 6120: 6112: 6103: 6102: 6100: 6099: 6084: 6082: 6078: 6077: 6074: 6073: 6071: 6070: 6065: 6060: 6055: 6050: 6045: 6040: 6035: 6029: 6027: 6021: 6020: 6018: 6017: 6012: 6008: 6004: 6000: 5995: 5990: 5985: 5980: 5975: 5953: 5948: 5943: 5938: 5933: 5928: 5923: 5918: 5913: 5907: 5905: 5899: 5898: 5896: 5895: 5890: 5886: 5878: 5872: 5866: 5862: 5852: 5848: 5838: 5830: 5826: 5822: 5816: 5812: 5806: 5802: 5796: 5792: 5774: 5770: 5760: 5756: 5749: 5747: 5738: 5734: 5733: 5725: 5723: 5722: 5715: 5708: 5700: 5691: 5690: 5687: 5686: 5684: 5683: 5678: 5672: 5670: 5666: 5665: 5663: 5662: 5657: 5652: 5647: 5642: 5637: 5632: 5627: 5622: 5617: 5612: 5604: 5599: 5598: 5593: 5588: 5583: 5578: 5574: 5569: 5563: 5561: 5554: 5541: 5540: 5537: 5536: 5534: 5533: 5528: 5522: 5520: 5513: 5512: 5510: 5509: 5503: 5501: 5494: 5493: 5491: 5490: 5484: 5482: 5475: 5474: 5472: 5471: 5462:(regulated by 5459: 5458: 5439: 5437: 5427: 5421: 5420: 5418: 5417: 5411: 5406: 5395: 5394: 5389: 5384: 5379: 5374: 5368: 5366: 5362: 5361: 5349: 5347: 5346: 5339: 5332: 5324: 5316: 5315: 5288:(4): 282–284. 5272: 5237: 5218:(1): 220–221. 5202: 5150: 5139:(2): 123–129. 5123: 5096: 5069:(4): 269–280. 5046: 5017:(4): e002639. 4997: 4978:(3): 282–288. 4962: 4933:(7): 435–442. 4910: 4896: 4887: 4860:(4): 281–287. 4844: 4825: 4806: 4795:(4): 689–690. 4779: 4744: 4695: 4644: 4593: 4539: 4512: 4461: 4446: 4419:(5): 445–453. 4400: 4339: 4304: 4253: 4194: 4131: 4082: 4033: 3984: 3973:(3): 119–123. 3957: 3927: 3900: 3899:PDQ Coenzyme Q 3875: 3852: 3840: 3819: 3790:(2): 574–594. 3774: 3753:(2): 131–139. 3733: 3719: 3699: 3664: 3611: 3557: 3528:(9): 697–700. 3517: 3508: 3479:(5): 449–456. 3460: 3434: 3381: 3332: 3292: 3254: 3235:(1): 122–124. 3219: 3200:(2): 230–234. 3184: 3173:(3): 288–292. 3157: 3136:(1): 195–204. 3116: 3075: 3034: 2971: 2908: 2842: 2779: 2716: 2676: 2606: 2576: 2513: 2496:"Coenzyme Q10" 2482: 2457:"Coenzyme Q10" 2420: 2403:"Coenzyme Q10" 2340: 2339: 2337: 2334: 2333: 2332: 2326: 2318: 2315: 2306: 2274: 2270: 2267: 2262: 2258: 2255: 2246: 2242: 2235: 2231: 2228: 2223: 2215: 2211: 2199: 2196:Dairy products 2191: 2186: 2185: 2182: 2176: 2175: 2172: 2166: 2165: 2162: 2156: 2155: 2152: 2146: 2145: 2142: 2136: 2135: 2132: 2126: 2125: 2122: 2116: 2115: 2112: 2107: 2101: 2100: 2097: 2091: 2090: 2087: 2081: 2080: 2077: 2071: 2070: 2067: 2061: 2060: 2057: 2052: 2048: 2047: 2044: 2038: 2037: 2034: 2028: 2027: 2024: 2018: 2017: 2014: 2008: 2007: 2004: 1998: 1997: 1994: 1989: 1983: 1982: 1979: 1973: 1972: 1969: 1963: 1962: 1959: 1952: 1951: 1948: 1941: 1940: 1937: 1932: 1926: 1925: 1922: 1918: 1917: 1914: 1910: 1909: 1906: 1903: 1899: 1898: 1895: 1891: 1890: 1887: 1883: 1882: 1879: 1876: 1872: 1871: 1868: 1864: 1863: 1860: 1856: 1855: 1852: 1849: 1845: 1844: 1841: 1835: 1834: 1831: 1825: 1824: 1821: 1815: 1814: 1811: 1805: 1804: 1801: 1796: 1794:Vegetable oils 1790: 1789: 1785: 1782: 1773: 1765: 1761: 1757: 1753: 1750: 1745: 1737: 1725: 1710: 1706: 1703: 1690: 1672:abdominal pain 1659: 1655: 1652: 1647: 1644:β-cyclodextrin 1624: 1620: 1616: 1613: 1608: 1600: 1593: 1590: 1585: 1581: 1577: 1573: 1569: 1566: 1559: 1552: 1544: 1541: 1513: 1509: 1506: 1501: 1493: 1489: 1478:emulsification 1449: 1445: 1442: 1440: 1437: 1432: 1428: 1416: 1408: 1397: 1394:blood pressure 1389: 1381: 1378: 1373: 1357: 1353: 1350: 1345: 1338: 1334: 1322: 1319: 1253:rhabdomyolysis 1244: 1222: 1221: 1214: 1203: 1179: 1176: 1172: 1171: 1157: 1153: 1141: 1137: 1134: 1129: 1125: 1121: 1118: 1099: 1087: 1079: 1075: 1072: 1053: 1021: 1013: 1005: 1001: 998: 959: 923: 875: 871: 868:Pseudomonadota 854: 853: 827: 825: 818: 812: 809: 796: 793: 792: 781: 777: 757: 741: 721: 710: 700: 697: 680: 669: 654: 647: 587: 583: 577: 574: 573: 568: 546: 545: 541:standard state 538: 535: 534: 521: 515: 512: 511: 507: 506: 494: 489: 486: 485: 481: 480: 477: 472: 469: 468: 465: 459: 458: 455: 451: 450: 444: 438: 437: 434: 428: 422: 417: 412: 409: 408: 404: 403: 401: 400: 397: 389: 388: 387: 384: 383: 381: 380: 376: 373: 372: 370: 366: 363: 362: 354: 353: 352: 349: 348: 346: 345: 332: 330: 318: 315: 314: 312: 311: 303: 301: 295: 294: 292: 291: 283: 281: 273: 270: 269: 267: 266: 258: 256: 250: 249: 239: 231: 230: 228: 227: 219: 217: 211: 210: 208: 207: 199: 197: 191: 190: 188: 187: 179: 177: 171: 170: 168: 167: 159: 157: 150: 147: 146: 144: 143: 135: 133: 128: 125: 124: 120: 119: 73: 69: 66: 65: 62: 58: 57: 53: 52: 48: 47: 41: 40: 36: 35: 23: 15: 13: 10: 9: 6: 4: 3: 2: 6465: 6454: 6451: 6449: 6448:Phenol ethers 6446: 6444: 6441: 6439: 6436: 6434: 6431: 6429: 6426: 6424: 6421: 6419: 6416: 6415: 6413: 6398: 6395: 6393: 6390: 6388: 6385: 6383: 6380: 6379: 6377: 6373: 6367: 6364: 6362: 6360: 6355: 6353: 6350: 6348: 6346: 6341: 6339: 6336: 6334: 6331: 6330: 6328: 6324: 6318: 6315: 6312: 6309: 6307: 6304: 6301: 6297: 6294: 6291: 6287: 6284: 6282: 6279: 6277: 6274: 6272: 6269: 6267: 6264: 6262: 6259: 6257: 6254: 6251: 6249: 6245: 6242: 6240: 6236: 6234: 6231: 6229: 6226: 6224: 6221: 6219: 6213: 6211: 6208: 6206: 6203: 6201: 6198: 6196: 6193: 6191: 6188: 6185: 6181: 6178: 6175: 6174:Ascorbic acid 6172: 6169: 6166: 6163: 6156: 6154: 6151: 6150: 6148: 6144: 6140: 6133: 6128: 6126: 6121: 6119: 6114: 6113: 6110: 6098: 6097: 6091: 6090: 6086: 6085: 6083: 6079: 6069: 6066: 6064: 6061: 6059: 6056: 6054: 6051: 6049: 6046: 6044: 6041: 6039: 6036: 6034: 6031: 6030: 6028: 6026: 6022: 6016: 6009: 6007: 6001: 5999: 5996: 5994: 5991: 5989: 5988:Molybdopterin 5986: 5984: 5981: 5979: 5976: 5973: 5969: 5965: 5961: 5957: 5954: 5952: 5949: 5947: 5944: 5942: 5941:Cofactor F430 5939: 5937: 5934: 5932: 5929: 5927: 5924: 5922: 5919: 5917: 5914: 5912: 5909: 5908: 5906: 5904: 5900: 5894: 5893:Coenzyme F420 5891: 5884: 5876: 5875:Phylloquinone 5873: 5870: 5869:Ascorbic acid 5867: 5860: 5856: 5853: 5846: 5842: 5834: 5827: 5820: 5817: 5810: 5807: 5800: 5797: 5790: 5786: 5782: 5778: 5775: 5768: 5764: 5761: 5754: 5751: 5750: 5748: 5746: 5742: 5739: 5735: 5731: 5728: 5721: 5716: 5714: 5709: 5707: 5702: 5701: 5698: 5682: 5679: 5677: 5674: 5673: 5671: 5667: 5661: 5658: 5656: 5653: 5651: 5648: 5646: 5643: 5641: 5638: 5636: 5633: 5631: 5628: 5626: 5623: 5621: 5618: 5616: 5613: 5611: 5607: 5601: 5600: 5597: 5594: 5592: 5589: 5587: 5584: 5582: 5575: 5573: 5570: 5568: 5565: 5564: 5562: 5558: 5555: 5553: 5548: 5544:Mitochondrial 5542: 5532: 5529: 5527: 5524: 5523: 5521: 5519: 5514: 5508: 5505: 5504: 5502: 5500: 5495: 5489: 5486: 5485: 5483: 5481: 5476: 5469: 5465: 5461: 5460: 5456: 5452: 5448: 5444: 5441: 5440: 5438: 5436: 5431: 5428: 5426: 5422: 5415: 5412: 5410: 5407: 5404: 5400: 5397: 5396: 5393: 5390: 5388: 5385: 5383: 5380: 5378: 5375: 5373: 5370: 5369: 5367: 5363: 5359: 5356: 5352: 5345: 5340: 5338: 5333: 5331: 5326: 5325: 5322: 5311: 5307: 5303: 5299: 5295: 5291: 5287: 5283: 5276: 5273: 5268: 5264: 5260: 5256: 5252: 5248: 5241: 5238: 5233: 5229: 5225: 5221: 5217: 5213: 5206: 5203: 5198: 5194: 5190: 5186: 5182: 5178: 5174: 5170: 5163: 5161: 5159: 5157: 5155: 5151: 5146: 5142: 5138: 5134: 5127: 5124: 5119: 5115: 5111: 5107: 5100: 5097: 5092: 5088: 5084: 5080: 5076: 5072: 5068: 5064: 5057: 5055: 5053: 5051: 5047: 5042: 5038: 5034: 5030: 5025: 5020: 5016: 5012: 5008: 5001: 4998: 4993: 4989: 4985: 4981: 4977: 4973: 4966: 4963: 4958: 4954: 4950: 4946: 4941: 4936: 4932: 4928: 4924: 4917: 4915: 4911: 4906: 4902: 4891: 4888: 4883: 4879: 4875: 4871: 4867: 4863: 4859: 4855: 4848: 4845: 4835: 4829: 4826: 4816: 4810: 4807: 4802: 4798: 4794: 4790: 4783: 4780: 4775: 4771: 4767: 4763: 4759: 4755: 4748: 4745: 4740: 4736: 4731: 4726: 4722: 4718: 4714: 4710: 4706: 4699: 4696: 4691: 4687: 4683: 4679: 4675: 4671: 4667: 4663: 4659: 4655: 4648: 4645: 4640: 4636: 4631: 4626: 4621: 4616: 4612: 4608: 4604: 4597: 4594: 4589: 4585: 4580: 4575: 4570: 4565: 4561: 4557: 4553: 4546: 4544: 4540: 4535: 4531: 4527: 4523: 4516: 4513: 4508: 4504: 4499: 4494: 4489: 4484: 4480: 4476: 4472: 4465: 4462: 4457: 4450: 4447: 4442: 4438: 4434: 4430: 4426: 4422: 4418: 4414: 4407: 4405: 4401: 4398: 4396: 4391: 4384: 4380: 4375: 4370: 4366: 4362: 4358: 4354: 4350: 4343: 4340: 4335: 4331: 4327: 4323: 4319: 4315: 4308: 4305: 4300: 4296: 4291: 4286: 4281: 4276: 4272: 4268: 4264: 4257: 4254: 4241: 4237: 4233: 4229: 4225: 4221: 4217: 4213: 4209: 4205: 4198: 4195: 4192: 4190: 4185: 4178: 4174: 4169: 4164: 4159: 4154: 4150: 4146: 4142: 4135: 4132: 4127: 4123: 4118: 4113: 4109: 4105: 4101: 4097: 4093: 4086: 4083: 4078: 4074: 4069: 4064: 4060: 4056: 4052: 4048: 4044: 4037: 4034: 4029: 4025: 4020: 4015: 4011: 4007: 4003: 3999: 3995: 3988: 3985: 3980: 3976: 3972: 3968: 3961: 3958: 3945: 3941: 3937: 3931: 3928: 3916: 3912: 3908: 3904: 3903: 3893: 3882: 3880: 3876: 3871: 3867: 3863: 3856: 3853: 3849:. April 2022. 3848: 3844: 3843: 3834: 3823: 3820: 3815: 3811: 3806: 3801: 3797: 3793: 3789: 3785: 3778: 3775: 3770: 3766: 3761: 3756: 3752: 3748: 3744: 3737: 3734: 3722: 3716: 3712: 3711: 3703: 3700: 3695: 3691: 3687: 3683: 3679: 3675: 3668: 3665: 3652: 3648: 3644: 3639: 3634: 3630: 3626: 3622: 3615: 3612: 3607: 3603: 3599: 3595: 3590: 3585: 3581: 3577: 3573: 3566: 3564: 3562: 3558: 3553: 3549: 3544: 3543:11577/2447079 3539: 3535: 3531: 3527: 3523: 3512: 3509: 3504: 3500: 3495: 3490: 3486: 3482: 3478: 3474: 3467: 3465: 3461: 3448: 3444: 3438: 3435: 3430: 3426: 3421: 3416: 3412: 3408: 3404: 3400: 3396: 3394: 3385: 3382: 3377: 3373: 3368: 3363: 3359: 3355: 3351: 3347: 3343: 3336: 3333: 3328: 3324: 3320: 3316: 3313:(1): 145–56. 3312: 3308: 3301: 3299: 3297: 3293: 3280: 3276: 3272: 3265: 3263: 3261: 3259: 3255: 3250: 3246: 3242: 3238: 3234: 3230: 3223: 3220: 3215: 3211: 3207: 3203: 3199: 3195: 3188: 3185: 3180: 3176: 3172: 3168: 3161: 3158: 3153: 3149: 3144: 3139: 3135: 3131: 3127: 3120: 3117: 3104: 3100: 3095: 3084: 3082: 3080: 3076: 3071: 3067: 3062: 3057: 3053: 3049: 3045: 3038: 3035: 3032: 3030: 3025: 3018: 3014: 3009: 3004: 2999: 2994: 2990: 2986: 2982: 2975: 2972: 2969: 2967: 2962: 2955: 2951: 2946: 2941: 2936: 2931: 2927: 2923: 2919: 2912: 2909: 2906: 2904: 2899: 2892: 2888: 2883: 2878: 2873: 2868: 2864: 2860: 2859:Int J Mol Sci 2856: 2849: 2847: 2843: 2840: 2838: 2833: 2826: 2822: 2817: 2812: 2807: 2802: 2798: 2794: 2790: 2783: 2780: 2777: 2775: 2770: 2763: 2759: 2754: 2749: 2744: 2739: 2735: 2731: 2730:Int J Mol Sci 2727: 2720: 2717: 2712: 2708: 2704: 2700: 2696: 2692: 2685: 2683: 2681: 2677: 2674: 2672: 2667: 2660: 2656: 2651: 2646: 2641: 2636: 2632: 2628: 2624: 2617: 2615: 2613: 2611: 2607: 2602: 2598: 2594: 2590: 2583: 2581: 2577: 2574: 2572: 2567: 2560: 2556: 2551: 2546: 2541: 2536: 2532: 2528: 2524: 2517: 2514: 2501: 2497: 2491: 2489: 2487: 2483: 2470: 2466: 2462: 2458: 2451: 2449: 2447: 2445: 2443: 2441: 2439: 2437: 2435: 2433: 2431: 2429: 2427: 2425: 2421: 2408: 2404: 2398: 2396: 2394: 2392: 2390: 2388: 2386: 2384: 2382: 2380: 2378: 2376: 2374: 2372: 2370: 2368: 2366: 2364: 2362: 2360: 2358: 2356: 2354: 2352: 2350: 2348: 2346: 2342: 2335: 2330: 2327: 2324: 2321: 2320: 2316: 2314: 2312: 2304: 2300: 2296: 2292: 2288: 2284: 2283:mitochondrial 2280: 2268: 2266: 2256: 2254: 2252: 2239: 2229: 2227: 2221: 2209: 2205: 2197: 2183: 2181: 2178: 2177: 2173: 2171: 2168: 2167: 2163: 2161: 2158: 2157: 2153: 2151: 2148: 2147: 2143: 2141: 2138: 2137: 2133: 2131: 2128: 2127: 2123: 2121: 2118: 2117: 2113: 2111: 2108: 2106: 2102: 2098: 2096: 2093: 2092: 2088: 2086: 2083: 2082: 2078: 2076: 2073: 2072: 2068: 2066: 2063: 2062: 2058: 2056: 2053: 2049: 2045: 2043: 2040: 2039: 2035: 2033: 2030: 2029: 2025: 2023: 2020: 2019: 2015: 2013: 2010: 2009: 2005: 2003: 2000: 1999: 1995: 1993: 1990: 1988: 1984: 1980: 1978: 1975: 1974: 1970: 1968: 1965: 1964: 1960: 1958:– white flesh 1957: 1954: 1953: 1949: 1946: 1943: 1942: 1938: 1936: 1933: 1931: 1927: 1923: 1920: 1919: 1915: 1912: 1911: 1907: 1904: 1900: 1896: 1893: 1892: 1888: 1885: 1884: 1880: 1877: 1873: 1869: 1866: 1865: 1861: 1858: 1857: 1853: 1850: 1846: 1842: 1840: 1837: 1836: 1832: 1830: 1829:sunflower oil 1827: 1826: 1822: 1820: 1819:grapeseed oil 1817: 1816: 1812: 1810: 1807: 1806: 1802: 1800: 1797: 1795: 1791: 1783: 1779: 1769: 1751: 1749: 1743: 1735: 1731: 1723: 1720: 1719:anticoagulant 1716: 1704: 1702: 1700: 1696: 1687: 1685: 1684:liver enzymes 1681: 1677: 1673: 1669: 1665: 1653: 1651: 1645: 1641: 1640:cyclodextrins 1637: 1633: 1630: 1614: 1612: 1606: 1598: 1597:Nanoparticles 1591: 1589: 1567: 1565: 1564: 1556: 1550: 1542: 1540: 1538: 1535: 1531: 1527: 1523: 1519: 1507: 1505: 1499: 1487: 1483: 1479: 1475: 1471: 1467: 1463: 1459: 1455: 1443: 1438: 1436: 1426: 1422: 1413: 1406: 1405:meta-analysis 1401: 1395: 1387: 1379: 1377: 1371: 1367: 1363: 1351: 1349: 1342: 1332: 1328: 1320: 1318: 1316: 1312: 1311: 1310:S. cerevisiae 1306: 1302: 1298: 1297: 1291: 1289: 1285: 1281: 1280: 1275: 1274: 1269: 1268: 1263: 1262: 1256: 1254: 1250: 1242: 1237: 1235: 1231: 1227: 1219: 1215: 1212: 1208: 1204: 1201: 1197: 1193: 1192:phenylalanine 1189: 1185: 1184: 1183: 1177: 1175: 1167: 1163: 1162: 1161: 1151: 1147: 1135: 1133: 1119: 1117: 1115: 1113: 1109: 1105: 1097: 1093: 1085: 1073: 1071: 1069: 1065: 1061: 1060: 1051: 1050: 1045: 1044: 1039: 1038: 1033: 1032: 1027: 1019: 1011: 999: 997: 995: 991: 987: 983: 979: 977: 972: 968: 963: 957: 953: 949: 945: 940: 937: 933: 929: 920: 916: 869: 865: 861: 850: 840: 835: 831: 828:This article 826: 817: 816: 810: 808: 806: 802: 790: 787:, scavenging 786: 782: 775: 771: 767: 763: 762: 761: 753: 751: 747: 739: 735: 731: 727: 718: 716: 706: 698: 696: 694: 690: 686: 677: 675: 667: 663: 660: 659:mitochondrial 651: 645: 641: 637: 633: 628: 590: 571: 564: 559: 542: 536: 533: 529: 528:Plastoquinone 525: 522: 519: 514: 513: 508: 503: 498: 495: 492: 488: 487: 484:Pharmacology 482: 478: 475: 471: 470: 466: 464: 463:Melting point 461: 460: 456: 453: 452: 445: 443: 440: 439: 418: 415: 411: 410: 405: 396: 392: 385: 371: 361: 357: 350: 342: 338: 337:DTXSID6046054 334: 333: 331: 321: 317: 316: 309: 305: 304: 302: 300: 297: 296: 289: 285: 284: 282: 276: 272: 271: 264: 260: 259: 257: 255: 252: 251: 247: 243: 240: 238: 236:ECHA InfoCard 233: 232: 225: 221: 220: 218: 216: 213: 212: 205: 201: 200: 198: 196: 193: 192: 185: 181: 180: 178: 176: 173: 172: 165: 161: 160: 158: 154: 149: 148: 141: 137: 136: 134: 131: 127: 126: 121: 116: 113: 63: 60: 59: 54: 46: 42: 37: 33: 28: 19: 6418:Antioxidants 6382:Folin method 6375:Measurements 6361:-butylphenol 6358: 6347:-butylphenol 6344: 6313:(coenzyme Q) 6310: 6296:Tocotrienols 6247: 6238: 6139:Antioxidants 6093: 6087: 5993:Mycofactocin 5983:Methanofuran 5950: 5903:non-vitamins 5737:Active forms 5602: 5591:Cytochrome c 5576: 5499:succinyl-CoA 5285: 5281: 5275: 5253:(17): 4752. 5250: 5246: 5240: 5215: 5211: 5205: 5172: 5168: 5136: 5132: 5126: 5109: 5105: 5099: 5066: 5062: 5014: 5010: 5000: 4975: 4971: 4965: 4930: 4926: 4904: 4900: 4890: 4857: 4853: 4847: 4828: 4809: 4792: 4788: 4782: 4760:(1): 42–48. 4757: 4753: 4747: 4712: 4708: 4698: 4657: 4653: 4647: 4610: 4606: 4596: 4559: 4556:Antioxidants 4555: 4525: 4521: 4515: 4478: 4474: 4464: 4455: 4449: 4416: 4412: 4387: 4356: 4352: 4342: 4320:(1): 24–34. 4317: 4313: 4307: 4270: 4266: 4256: 4244:. Retrieved 4211: 4207: 4197: 4181: 4148: 4144: 4134: 4099: 4095: 4085: 4050: 4046: 4036: 4001: 3997: 3987: 3970: 3966: 3960: 3948:. Retrieved 3939: 3930: 3918:. Retrieved 3898: 3861: 3855: 3838: 3822: 3787: 3783: 3777: 3750: 3746: 3736: 3724:. Retrieved 3709: 3702: 3680:(1): 74–79. 3677: 3673: 3667: 3655:. Retrieved 3628: 3624: 3614: 3579: 3575: 3525: 3521: 3511: 3494:10261/129020 3476: 3472: 3451:. Retrieved 3437: 3405:(1): 37–44. 3402: 3399:Jimd Reports 3398: 3392: 3384: 3349: 3345: 3335: 3310: 3306: 3283:. Retrieved 3274: 3232: 3228: 3222: 3197: 3193: 3187: 3170: 3166: 3160: 3133: 3129: 3119: 3107:. Retrieved 3102: 3051: 3047: 3037: 3021: 2988: 2984: 2974: 2958: 2925: 2922:Antioxidants 2921: 2911: 2895: 2865:(18): 6695. 2862: 2858: 2829: 2796: 2792: 2782: 2766: 2736:(23): 9299. 2733: 2729: 2719: 2694: 2690: 2663: 2630: 2627:Antioxidants 2626: 2592: 2588: 2563: 2530: 2526: 2516: 2504:. Retrieved 2473:. Retrieved 2411:. 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Index


Preferred IUPAC name
/ˌkˌkjuːˈtɛn/
CAS Number
303-98-0
JSmol
Interactive image
ChEBI
CHEBI:46245
ChEMBL
ChEMBL454801
ChemSpider
4445197
ECHA InfoCard
100.005.590
Edit this at Wikidata
KEGG
C11378
PubChem
5281915
UNII
EJ27X76M46
CompTox Dashboard
DTXSID6046054
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
Melting point

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