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Coenzyme Q


DATA No : VCQ0013 INFORMANT : Tetsuya Nakamura

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

COMMON NAME: Q acid I
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:lEtOHmax oxidized form 275, reduced form 290 mm(Ref. 0035)

IR SPECTRA:(CCl4)sim2650, 1700, (COOH), 1660, 1650, 1610 cm-1 (quinone)(Ref. 0035)

NMR SPECTRA:(CCl4) trans compound 8.27 (s, 3, C=CCH3), 8.09 (s, 3, ring CH3), 7.72 (b, 4, C=CCH2, CH2COO) , 6.92 (d, 2, ring CH2), 6.12 (s, 6, OCH3). cis compound 8.35 (s, 3, C=CCH3), 7.60 (b, 4, C=CCH2, CH2COO) . (Ref. 0035)

MASS SPECTRA:m/e 308 (M), 293 (M - CH3), 247, 235.(Ref. 0035)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
Methanolic KOH (10%) (2 ml) was added to a solution of 2,3-dimethoxy-5-methyl-6-(3'-methyl-5(5'-methoxycarbonyl-2'-pentenyl)-1,4-benzoquinone (20mg) and pyrogallol (200 mg) in methanol (2 ml) and the mixture was heated at 70 deg for 1 hr under N2. Water was added and the reaction mixture was acidified with 10% HCl and extracted with ether. The ether extracts were shaken with a solution of FeCl3 (1 g) in 30% methanol (10 ml) and the ether layer was separated. The residue of the ether layer was purified by thin-layer chromatography using chloroform-ethanol (9:1) to give (VCQ0013) as an orange oil. Yield 10 mg (52.4 %). (Ref. 0035)
METABOLISM
Trans-2,3-dimethoxy-5-methyl-6-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-benzoquinone (Q acid I) (VCQ0013) was obtained in the urine as one of metabolites of ubiquinone-7 administered in rats and rabbits . The disulfate of (VCQ0013) was found also.(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.