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Vitamin K


DATA No : VVK0009 INFORMANT : Tetsuya Nakamura

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

COMMON NAME: Menaquinone 8 / Menaquinone MK8/ Vitamin K2(40)/ Vitamin MK8.
SYMBOL: MK-8
FORMULA: C51H72O2 MOL.WT (average) : 717.116


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:56degC(Ref. 0010)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA: E1%1cm (248mm)= 268, in petroleum ether(Ref. 0010)

IR SPECTRA:

NMR SPECTRA:

MASS SPECTRA:

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE

[Table 0001] (Ref. 0022)

[Table 0002] (Ref. 0022)
CHEMICAL SYNTHESIS
Condensation of 2-methyl-1,4-naphthohydroquinone (I) with farnesylfarnesyllinalool (II). I (27.5g) is dissolved in 65 ml of dry dioxane, 1.5 g of zinc chloride, and 3.5 ml of borontrifluoride etherate are added with stirring, and the mixture is heated to 50deg. A solution of 0.87 mole of II per mole of I in 25 ml of dry dioxane is added, and the reaction mixture is stirred for 20 min 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 petroleum ether, the solution cooled to -50deg. The precipitate centrifuged. The precipitate dissolved in 100 ml of ether, 20 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. (Ref. 0017)
METABOLISM

GENETIC INFORMATION

[Table 0001]
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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[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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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.