Vitamin K

DATA No : VVK0011 INFORMANT : Tetsuya Nakamura

NAME : 1,4-Naphthalenedione,2-methyl-3-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)- / 1,4-Naphthoquinone,2-methyl-3-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-

COMMON NAME	:	Menaquinone 10 / Menaquinone MK10 / Vitamin K₂₍₅₀₎ / Vitamin MK10.
SYMBOL	:	MK10
FORMULA	:	C₆₁H₈₈O₂ MOL.WT (average) : 853.350

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	E¹^%₁_c_m (248mm) =224, in petroleum ether, b.p. 80-105.(Ref. 0017)

IR SPECTRA	:

NMR SPECTRA	:

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Concentration in human liver
[Table 0001] (Ref. 0022).
Distribution in human mitochondrial and microsomal fractions
[Table 0002] (Ref. 0022).

CHEMICAL SYNTHESIS

Menaquinone-10 (Ref. 0011) is prepared in analogy to menaquinone-9 (Ref. 0010) from 7g of farnesylfarnesylgeranyllinalool, 7 g of 2-methyl-1,4-naphthohydroquinone (I) is dissolved in 50 ml of dry dioxane, 0.5 g of zinc chloride and 1 ml of boron trifluoride etherate in 65 ml of dry dioxane, 1.5 g of zinc chloride of borontrifluoride etherate are added with stirring, and the mixture is heated to 55

- 60

under nitrogen. The crude product, m.p. 56

., is chromatographed on Hostalen, yielding pure menaquinone-10 as fine yellow crystals, melting at 62

. (Ref. 0017)

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES

[0010]

AUTHOR	:	Sommer,P., and Kofler,M.
TITLE	:	Physicochemical Properties and Methods of Analysis of Phylloquinones, Menaquinones, Ubiquinones, and Related Compounds. PubMed ID:5340867
JOURNAL	:	Vitamins and Hormones
VOL	:	24 PAGE : 349 -399 (1966)

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[0011]

AUTHOR	:	Bristol, J. A., Ratcliffe, J. V., Roth, D. A., Jacobs, M. A., Furie, B. C., and Furie, B.
TITLE	:	Biosynthesis of prothrombin: intracellular localization of the vitamin K-dependent carboxylase and the sites of gamma-carboxylation PubMed ID:8839851
JOURNAL	:	Blood.
VOL	:	88 PAGE : 2585-2593 (1996)

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[0017]

AUTHOR	:	Mayer,H., and Isler,O.
TITLE	:	Synthesis of vitamin K.
JOURNAL	:	Methods in Enzymology
VOL	:	18 PAGE : 491 -547 (1971)

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[0022]

AUTHOR	:	Usui, Y., Nishimura, N., Kobayashi, N., Okanoue, T., Kimoto, M., and Ozawa, K.
TITLE	:	Measurement of vitamin K in human liver by gradient elution high-performance liquid chromatography using platinum-black catalyst reduction and fluorimetric detection PubMed ID:2753953
JOURNAL	:	J Chromatogr.
VOL	:	489 PAGE : 291-301 (1989)

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