Ubiquinones
Title: Ubiquinones
Additional Names: Coenzymes Q; mitoquinones; SA; Q-275
Literature References: A group of lipid-soluble benzoquinones involved in electron transport in mitochondria, i.e., in the oxidation of succinate or reduced nicotine adenine dinucleotide (NADH) via the cytochrome system. Occurs in the majority of aerobic organisms, from bacteria to higher plants and animals. Ubiquinone structures, analogous to the menaquinones, q.v., are based on the 2,3-dimethoxy-5-methylbenzoquinone nucleus with a variable terpenoid side chain contg one to twelve mono-unsaturated trans-isoprenoid units with 10 units being the most common in animals. According to the existing dual system of nomenclature the compds can be described as: coenzyme Qn in which n = 1-12, or ubiquinone(x) in which x designates the total number of carbon atoms in the side chain and can be any multiple of 5. Differences in properties are due to the difference in length of the side chain. Naturally occurring members are the coenzymes Q6-Q10. The entire series has been prepd synthetically. Recent syntheses of ubiquinone 50: S. Terao et al., J. Org. Chem. 44, 868 (1979); Y. Naruta, ibid. 45, 4097 (1980); K. Sato et al., Chem. Commun. 1982, 153. Reviews: Ciba Foundation Symposium on Quinones in Electron Transport, Wolstenholme, O'Connor, Eds. (Churchill, London, 1961) 453 pp; Wagner, Folkers, Vitamins and Coenzymes (Interscience, New York, 1964) pp 435-468; Crane in Progr. Chem. Fats Lipids vol. 7(2), Holman, Ed. (Pergamon Press, 1964) pp 267-289; Methods Enzymol. 18C, 135-237 (1971); R. A. Morton in The Vitamins vol. V, W. H. Sebrell, R. S. Harris, Eds. (Academic Press, New York, 2nd ed., 1972) pp 355-391. Series of books: Biomedical and Clinical Aspects of Coenzyme Q vols. 1-3, K. Folkers, Y. Yamamura, Eds. (Elsevier, New York, 1977, 1980, 1981).
 
Derivative Type: Ubiquinone 50
CAS Registry Number: 303-98-0
Additional Names: Coenzyme Q10; CoQ10; coenzyme Q-199; ubidecarenone; ubiquinone 10
Manufacturers' Codes: NSC-140865
Trademarks: Adelir (Merck KGaA); Caomet (AstraZeneca); Decafar (Lafare); Decorenone (Italfarmaco); Dymion (Pulitzer); Heartcin (Ohta); Inokiten (Nippon Yakuhin); Iuvacor (Sanofi-Synthelabo); Mitocor (Zambon); Neuquinon (Eisai); Taidecanone (Taiyo); Ubicardio (Tosi); Ubicor (Magis); Ubidenone (Esseti); Ubifactor (San Carlo); Ubimaior (Chiesi); Ubisan (Leben's); Ubiten-50 (Lifepharma); Ubivis (AGIPS); Udekinon (Tobishi)
Molecular Formula: C59H90O4
Molecular Weight: 863.34
Percent Composition: C 82.08%, H 10.51%, O 7.41%
Literature References: Clinical evaluation in early Parkinson disease: C. W. Shults et al., Arch. Neurol. 59, 1541 (2002).
 
Derivative Type: Ubichromenol 50
CAS Registry Number: 2382-48-1
Literature References: Cyclic isomer of ubiquinone 50.
 
Therap-Cat: Cardiotonic; coenzyme Q10 as antiparkinsonian.

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