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Coenzyme Q


DATA No : VCQ0015 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-5-methyl--6-(5'-carboxy-3'-hydroxy--3'-methylpentyl)-1,4-benzoquinone lactone

COMMON NAME: Q lactone
SYMBOL:
FORMULA: C16H20O6 MOL.WT (average) : 308.326


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax 276 nm (E1%1cm = 503) (in ethanol).(Ref. 0002)

IR SPECTRA:1380(CH3), 1614 and 1652 (quinone), 1767 (lactone), and 2840 mm (OCH3) (in chloroform).(Ref. 0002)

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
(a) HCl (10%) (0.5 ml) was added to a solution of Q acid-I (VCQ0013) (1 mg) in tetrahydrofuran (0.5 ml) and the mixture heated at 75deg C for 1.5 h under N2. Water was added and the reaction mixture extracted with ether. The ether extracts were worked up in the usual manner to give an oil. The oil was purified by thin-layer chromatography using ether-chloroform-ethanol (3 : 2: 1) to give Q lactone as an orange oil : yield 0.2 mg (20.0%).(Ref. 0035) (b) To a solution of 24.1 g of ceric sulfate in 300 ml of water (acidified with 7.5 ml of concentrated sulfuric acid) is added with stirring within approx 10 minutes a solution of 7.9 g of crude hydroxy acid (Ref. 0002) in 390 ml of methanol. The reaction mixture is stirred for 15 minutes , then diluted with 850 ml of water and extracted with eight 100-ml portions of ether. The combined ether extracts are washed with three 75-ml portions of saturated sodium chloride solution, dried over magnesium sulfate, and evaporated in vacuo to give 7.1 g (90.5%) of crude quinone . The product is chromatographed on 70 g of aluminum oxide (activity grade II). It is dissolved in 6 ml of chloroform and 20 ml of ether, put on the column , and eluted with ether. In this manner 4.3 g of oily quinone (Q lactone) is obtained which can be distilled at 190deg-195deg/0.05 mm.
[Table 0001] (Ref. 0002)
METABOLISM
2,3-Dimethoxy-5-methyl--6-(5'-carboxy-3'-hydroxy--3'-methylpentyl)-1,4-benzoquinone lactone(VCQ0015) was proved to be an artifact formed from the conjugate of Q acid I (VCQ0013) during the hydrolysis step. (Ref. 0033)
GENETIC INFORMATION

NOTE

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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[0033]
AUTHOR:Imada, I., Watanabe, M., Matsumoto, N., and Morimoto, H.
TITLE:Metabolism of ubiquinone-7 PubMed ID:5459540
JOURNAL:Biochemistry.
VOL:9 PAGE : 2870-2878 (1970)
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[0035]
AUTHOR:Watanabe, M., Imada, I., and Morimoto, H.
TITLE:Synthesis of ubiquinone-7 metabolites PubMed ID:5459541
JOURNAL:Biochemistry.
VOL:9 PAGE : 2879-2886 (1970)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.