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Coenzyme Q


DATA No : VCQ0011 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-5-methyl-1,4-benzoquinone

COMMON NAME: Coenzyme Q0
SYMBOL: Co Q0
FORMULA: C9H10O4 MOL.WT (average) : 182.173


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BIOLOGICAL ACTIVITY
The kinetics of ascorbate (AscH-) and epinephrine (EP) oxidation in the presence of 2,3-dimethoxy-5-methyl-1,4-benzoquinone(VCQ0011) were studied in 0.05M phosphate buffer, pH 7.4, at 37deg by using a Clark electrode and ESR techniques. (VCQ0011) at nanomolar concentrations displayed a pronounced catalytic effect on AscH- oxidation which exceeded that of all reported organic catalysts tested in this system. The capability of (VCQ0011) to catalyze the oxidation of EP exceeded by approximately 25 times that of adrenochrome, a quinoid product of EP oxidation. (VCQ0011) may be considered , in combination with AscH-, as a potential
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:62degC(Ref. 0017)

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CHEMICAL SYNTHESIS
A solution of potassium nitrodisulfonate (6.0 g, 0.022 mole) and sodium phosphate (2.84 g, 0.02 mole) in water (10 is mixed at 25 with a solution of 2,3- dimethoxy-6-methylaniline hydrochloride (2.03 g, 0.01 mole) in water (20 ml) . After 0.5 hour the mixture is acidified with glacial acetic acid (4.0 ml), stirred for an additional 0.5 hour, and extracted with methylene chloride. The dried (MgSO4) extracts are evaporated in vacuo to an orange oily residue which rapidly crystallizes. The yield of coenzyme Q 0 is 1.74 g (95%); m.p. 55deg-57deg. A small sample is sublimed at 45deg/1 mm, giving the quinone with m.p. 59deg. Ultraviolet absorption maximum at 264 nm ( e=13,400) (in methanol). The infrared absorption spectrum shows bands at 1660, 1605, 1450, 1320, 1280, 1220, 1140, 1085, and 885 cm-1 (in CCl4). (Ref. 0002)
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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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[0010]
AUTHOR:Roginsky, V. A., Bruchelt, G., and Bartuli, O.
TITLE:Ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) as effective catalyzer of ascorbate and epinephrine oxidation and damager of neuroblastoma cells PubMed ID:9413934
JOURNAL:Biochem Pharmacol.
VOL:55 PAGE : 85-91 (1998)
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[0013]
AUTHOR:Kishi, T., Okamoto, T., Takahashi, T., Goshima, K., and Yamagami, T.
TITLE:Cardiostimulatory action of coenzyme Q homologues on cultured myocardial cells and their biochemical mechanisms PubMed ID:8241709
JOURNAL:Clin Investig.
VOL:71 PAGE : S71-75 (1993)
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[0017]
AUTHOR:Yu, C. A., Nagoaka, S., Yu, L., and King, T. E.
TITLE:Evidence of ubisemiquinone radicals in electron transfer at the cytochromes b and c1 region of the cardiac respiratory chain PubMed ID:6252851
JOURNAL:Arch Biochem Biophys.
VOL:204 PAGE : 59-70 (1980)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.