Vitamin K

DATA No : VVK0010 INFORMANT : Tetsuya Nakamura

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

COMMON NAME	:	Menaquinone 9 / Menaquinone MK9 / Vitamin K₂ ₍₄₅₎ / Vitamin MK9.
SYMBOL	:	MK-9
FORMULA	:	C₅₆H₈₀O₂ MOL.WT (average) : 785.233

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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	56-57C(Ref. 0017)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:

DENSITY	:

SOLUBILITY	:

SPECTRAL DATA

UV SPECTRA	:	E¹^%₁_c_m (248mm) =246, in petroleum ether, 80-105(Ref. 0017)

IR SPECTRA	:

NMR SPECTRA	:

MASS SPECTRA	:

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

[Table 0001] (Ref. 0022)

[Table 0002] (Ref. 0022)

CHEMICAL SYNTHESIS

Seven grams 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. A solution of 7.5 g of solanesol in 30 ml of dry dioxane is added, and the reaction mixture is stirred for 1 hour longer. After cooling water and ether are added, the layers were separated and the etheral layer is washed. The ether solution is evaporated. The residue is dissolved in 200 ml of ether, 10 g of dry silver oxide is added and the mixture shaken for 30 min.
After filtration the etheral solution is evaporated in vacuo, the residue dissolved in petroleum ether and chramatogphed through a colum of aluminum oxide. Yield : 120 mg. m.p. 56

-57

. (Ref. 0017)

METABOLISM

Rats were made vitamin K-deficiency by feeding them diet devoid of vitamin K. after one week, circulating prothrombin concentrations were between 5 and 10% of initial values and various amounts of phylloquinone, menaquinone-4, and menaquinone-9 were given in a single dose either subcutaneously, orally, or colorectally. The relative 'vitamin K acitivties' of these compounds were assessed by comparing their activity to support prothrombin synthesis after subcutaneous injection. The stimulation of prothormbin synthesis by menaquinone-9 lasted much longer than that by the two other K-vitamers, resulting in a substantially higher 'vitamin K activity' of menaquinone-9.(Ref. 0032)
[Table 0003] (Ref. 0032)

GENETIC INFORMATION

NOTE

REFERENCES

[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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[0032]

AUTHOR	:	Groenen-van Dooren, M. M., Ronden, J. E., Soute, B. A., and Vermeer, C.
TITLE	:	Bioavailability of phylloquinone and menaquinones after oral and colorectal administration in vitamin K-deficient rats PubMed ID:7575640
JOURNAL	:	Biochem Pharmacol.
VOL	:	50 PAGE : 797-801 (1995)

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