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Coenzyme Q


DATA No : VCQ0016 INFORMANT : Tetsuya Nakamura

NAME : 2,3-Dimethoxy-6-(9'-fluorodecyl)-1,4-benzoquinone

COMMON NAME:
SYMBOL: 9FQ
FORMULA: C19H29O4F1 MOL.WT (average) : 340.430


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BIOLOGICAL ACTIVITY
9FQ is active (greater than 50% the activity of 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone) when used as electron acceptors for succinate-ubiquinone reductase. 9FQ is active when used as an electron donor for ubiquinol-cytochrome c reductase or as an electron mediator for succinate-cytochrome c reductase. The lack of significant chemical shift for 9FQ, suggest that the benzoquinone ring is bound near the paramagnetic cytochrome b heme.(Ref. 0016)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:UVEtOH:oxid., 278 nm, red., 290 nm.(Ref. 0016)

IR SPECTRA:

NMR SPECTRA:1H NMR (CDCl3): 0. 95 (q. 3H), 1.31 (m, 12H), 1.59 (m, 2H), 1.59 (m, 2H), 1.98 (s, 3H), 2.45 (t, 2H), 3.97 (s, 6H), 4.63 (m, 1H); 19F NMR (CDCl3): -94.8ppm (m) (Ref. TFA.) (Ref. 0016)

MASS SPECTRA:m/e = 340.2046.(Ref. 0016)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

CHEMICAL SYNTHESIS
To investigate the protein-ubiquinone interaction in the bovine heart mitochondrial succinate-cytochrome c reductase region of the respiratory chain, a fluorine substituted ubiquinone derivative, 2,3-dimethoxy-6-(9'-fluorodecyl)-1,4-benzoquinone (9FQ) was synthesized. 9FQ was synthesized by radical coupling of Q0 and bis (10-fluoroundecanoyl) peroxide. (Ref. 0016)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0016]
AUTHOR:Yang, F., Yu, L., He, D. Y., and Yu, C. A.
TITLE:Protein-ubiquinone interaction in bovine heart mitochondrial succinate-cytochrome c reductase. Synthesis and biological properties of fluorine substituted ubiquinone derivatives PubMed ID:1657937
JOURNAL:J Biol Chem.
VOL:266 PAGE : 20863-20869 (1991)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.