Coenzyme Q

DATA No : VCQ0012 INFORMANT : Tetsuya Nakamura

NAME : 2,5-Cyclohexadiene-1,4-dione, 2-(3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyl- 2,6,10,14,18, 22,26,30,34,38,42,46-octatetracontadodecaenyl)-5,6-dimethoxy-3-methyl-, (all-E)- / p-Benzoquinone, 2-(3,7,11,15,19,23,27,31,35,39,43,47-dodecamethyl- 2,6,10,14,18, 22,26,30,34,38,42,46-octatetracontadodecaenyl)-5,6-dimethoxy-3-methyl-. 2,3-Dimethoxy- 4-methyl-5- dodecaprenyl -1,4-benzoquinone

COMMON NAME	:	Coenzyme Q₁₂ / trans-Coenzyme Q₁₂ / Ubiqui none 12 / Ubiquinone Q-12
SYMBOL	:	Co Q₁₂
FORMULA	:	C₆₉H₁₀₆O₆ MOL.WT (average) : 1031.576

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CHEMICAL SYNTHESIS

To a solution of 0.25 g of 2,3-dimethoxy-5-methylbenzohydroquinone and 0.85 g of natural dodecaprenol (possessing eight cis and three trans double bonds counting from the terminal hydroxy-containing isoprenoid unit) in 25 ml of freshly distilled dioxane is added 0.5 ml of freshly distilled BF₃ etherate. After stirring this mixture for 4 hours , it is poured into 300 ml of ether and 200 ml of water. The organic phase is separated, washed with water, and then vigorously shaken with excess aqueous methanolic ferric chloride solution. The ether layer is again separated washed with water, and dried. The residue obtained upon evaporation of the solvent subjected to preparative layer chromatography on silica gel G plates (1.0 mm) developed in hexane-ether (9:1) . Ubiquinone-12 appears as an orange band of higher Rf value than the t of a much larger orange band (2,3-dimethoxy- 5-methyl-1,4-benzoquinone ). Further purification is achieved by preparative thin-layer chromatography using hexane-ether (95:5) as developing solvent. The plates are developed five times, the ubiquinone-12 removed, and this chromatographic process is repeated. In this way, 15 mg of ubiquinone-12 is obtained as an orange viscous oil. The ultraviolet adsorption maximum is at 272 nm (in hexane). Nuclear magnetic resonance spectrum (chemical shifts in t; CCl₄): multiplet at 4.97 (12 vinylic H), singlet at 6.12 (2OCH₃), doublet at 6.92 (J~6.5 Hz) (CH₂ next to ring), multiplet at 7.7-8.2 (side chain methylene), signals at 8.30 (cis methyl at C-3

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REFERENCES

[0002]

AUTHOR	:	Mayer,H., and Isler, O.
TITLE	:	Synthesis of ubiquinones
JOURNAL	:	Methods in Enzymology
VOL	:	18 PAGE : 182 -213 (1971)

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[0008]

AUTHOR	:	Daves, G. D., Jr., Folkers, K., Lenaz, G., Fukawa, H., and Shimizu, T.
TITLE	:	Synthesis and coenzymatic activity of ubiquinone-12 PubMed ID:5726549
JOURNAL	:	Int Z Vitaminforsch.
VOL	:	38 PAGE : 65-70 (1968)

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