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	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	l^E^t^O^H_m_a_x (E¹^%₁_c_m ) oxidized form 278 (505), reduced form 291 mm(112), DE¹^%₁_c_m at 278 mm 432.(Ref. 0035)

IR SPECTRA	:	(CCl₄)2600, 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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