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Coenzyme Q


DATA No : VCQ0014 INFORMANT : Tetsuya Nakamura

NAME : 2,3-dimethoxy-5-methyl-6-(3'-carboxy-3'-methylpropyl)-1,4-benzoquinone

COMMON NAME: Q acid II
SYMBOL:
FORMULA: C14H18O6 MOL.WT (average) : 282.289


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

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OPTICAL ROTATION:

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SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lEtOHmax (E1%1cm ) oxidized form 278 (505), reduced form 291 mm(112), DE1%1cm at 278 mm 432.(Ref. 0035)

IR SPECTRA:(CCl4)sim2600, 1700, (COOH), 1660, 1650, 1610 cm-1 (quinone).(Ref. 0035)

NMR SPECTRA:(CCl4) 8.75 (d, 3, side chain CH3), 8.6-8.1(m, 2, CH2), 8.03 (s, 3, ring CH3), 7.54 (t, 2, ring CH2), 7.46 (b, 1, CHCOO), 6.10 (s, 6, OCH3), -1.04 (b, 1, COOH). (Ref. 0035)

MASS SPECTRA:m/e 282 (M), 249, 236, 221, 208, 195, 149, 74. (Ref. 0035)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
ON(SO3K)2(3 g) in water (60 ml) was added to a solution of X (1.4 g) in 2% NaOH (12 ml) and stirred for 2 hr at room temperature. The reaction mixture was acidified with 10% HCl and extracted with ether. The ether extracts were worked up in the usual manner to give an orange oil (1.3 g) . The oil was purified by column chromatography on silicic acid (50 g) containing 3% of water eluting with chloroform to afford <0014> as a red oil: yield 1.36 g (92.3%).(Ref. 0035)
METABOLISM
2,3-dimethoxy-5-methyl-6-(3'-carboxy-3'-methylpropyl)-1,4-benzoquinone (Q acid II) (VCQ0014) was obtained in the urine as one of metabolites of ubiquinone-7 administered in rats and rabbits. (Ref. 0033) (Ref. 0034)
GENETIC INFORMATION

NOTE

REFERENCES
[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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[0034]
AUTHOR:Watanabe, M., Toyoda, M., Imada, I., and Morimoto, H.
TITLE:Ubiquinone and related compounds. XXVI. The urinary metabolites of phylloquinone and a-tocopherol. PubMed ID:4833371
JOURNAL:Chem. Pharm. Bull.
VOL:22 PAGE : 176 -182 (1974)
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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.