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Coenzyme Q


DATA No : VCQ0006 INFORMANT : Tetsuya Nakamura

NAME : 2,5-Cyclohexadiene-1,4-dione, 2,3-dimethoxy-5-methyl-6- (3,7,11,15,19-pentamethyl-2,6,10,14, 18- eicosapentaenyl)-

COMMON NAME: p-Benzoquinone, 2,3-dimethoxy-5-methyl-6- (3,7,11,15,19-pentamethyl-2,6,10,14,18- eicosa pent aenyl)- / (all- E)-. p-Benzoquinone, 2,3-dimethoxy-5-methyl-6- (3,7,11,15,19-pentamethyl- 2,6,10, 14,18- eicosapentaenyl)- / Coenzyme Q5/ Ubiquinone 25 / Ubiquinone 5 / Ubiquinone Q5.
SYMBOL: Co Q5
FORMULA: C34H49O4 MOL.WT (average) : 521.750


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:20deg(Ref. 0028)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax 270 mm, E1%1cm = 292 in petroleum ether(Ref. 0037)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Isolation and separation---One kilogram of dry cells of Escherichia coli 08 was extracted by shaking 15 h with 5 litters of ether-ethanol (3:1). The filtrate was evaporated in vacuo, and the residue was dissolved in 300ml of aqueous methanol (95%). After addition of 300 ml of hexane, the mixture was filtered, and the organic phase was separated. The aqueous phase was further shaken with 150 ml of hexane, and the combined extracts were dried over Na2SO4. The solvent was evaporated, and the the residue (14 g) was dissolved in 80 ml of hexane. The orange-brown solution was chromatographed on a column of silica gel (5.2 x 90 cm). The column was developed by elution with 3 liters of hexane followed by increasing one-percent increments of ether in hexane in 3-liter portions, beginning with 1 % ether in hexane. The ubiquinones were eluted with 5% ether in hexane and were collected in two portions.
The first of these fractions contained practically pure Q8. The residue obtained from the second fraction was dissolved in a small volume of ether and streaked on silica gel G plates (0.5-1 mm). The plates were developed in d chloroform, air dried, and again developed in chloroform. This procedure was repeated three times. The upper and lower halves of the yellow quinone band (1-2 cm wide) were collected separately and eluted with ether. The material obtained from the lower half of the Q-band was subjected to the thin layer chroamtographic procedure described above. Four successive separations were carried out in this manner; each time the upper half of the yellow quinone band was discarded. Finally, a sample was obtained which on chromatography on silicon-coated paper proved to be pure ubiquinone-5. Q8, Q7, Q6, and Q5 were present to different extents in the intervening fractions.
[Table 0001] (Ref. 0032)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0028]
AUTHOR:Crane, F. L., and Barr, R. (1985) Chemical structure and properties of coenzyme Q related compunds, in Coenzyme Q (Lenaz, G., ed), pp1-37, John Wiley & Sons Ltd.
TITLE:
JOURNAL:
VOL: PAGE : - ()
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[0032]
AUTHOR:Friis, P., Daves, G. D., Jr., and Folkers, K.
TITLE:Isolation of ubiquinone-5, new member of ubiquinone group PubMed ID:5337718
JOURNAL:Biochem Biophys Res Commun.
VOL:24 PAGE : 252-256 (1966)
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[0037]
AUTHOR:Sommer,P., and Kofler,M.
TITLE:Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, Plastoquinones, Menadione, and Related Compounds. PubMed ID:5340867
JOURNAL:Vitamins and Hormones
VOL:24 PAGE : 349 -399 (1966)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.