81818-54-4

Basic information

• Product Name: 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone
• Synonyms: 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone;Einecs 279-833-9;Dry Vitamin K1 5% SD
• CAS NO: 81818-54-4
• Molecular Formula: C₃₁H₄₆O₂
• Molecular Weight: 450.69574
• EINECS: 279-833-9
• Mol File: 81818-54-4.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone(81818-54-4)
• EPA Substance Registry System: 2-methyl-3-(3,7,11,15-tetramethylhexadec-2-enyl)-1,4-naphthoquinone(81818-54-4)

Safety Data

• Hazardous Substances Data: 81818-54-4(Hazardous Substances Data)

Usage

InChI:InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+

Upstream product

• 58-27-5 menadione 
• 112212-56-3 C₁₃H₂₆Sn 
• 51287-54-8 3-(phenylsulfanyl)isobenzofuran-1(3H)-one 
• 97804-50-7 1,4,4a,9a-tetrahydro-4a-methyl-(1α,4α,4aα,9aα)-1,4-methanoanthracene-9,10-dione 
• 65592-98-5 1-chloro-3,7,11,15-tetramethylhexadec-2-ene 
• 76524-59-9 1-bromo-3,7,11,15-tetramethylhexadec-2-ene 
• 81818-56-6 4-methoxy-2-methyl-3-phytyl-1-naphthalenol 
• 81818-55-5 4-methoxy-3-methyl-2-phytyl-1-naphthalenol 
• 25486-55-9 vitamin K epoxide 
• 87798-16-1 3-bromo-2-methyl-1,4-bis-(dimethyl-t-butylsilyl)-1,4-dihydroxyphthalene 
• 39055-47-5 2-bromo-3-methylnaphthohydroquinone 
• 943232-38-0 (7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide 
• 76672-80-5 (E)-6,10,14,18-tetramethyl-5-nonadecene-2-yne 
• 31599-79-8 2-(chloromethyl)-3-methylnaphthalene-1,4-dione 

Downstream Products

• 502-69-2 6,10,14-Trimethyl-2-pentadecanon 
• 25486-55-9 vitamin K₁ epoxide 
• 19274-66-9 vitamin K₁ chromenol 
• 23397-22-0 2-(3-hydroperoxy-3,7,11,15-tetramethyl-hexadec-1-en-t-yl)-3-methyl-[1,4]naphthoquinone 
• 25486-55-9 Vitamin K₁ 2,3-epoxide 

Relevant articles and documents

Indirect inhibition of vitamin K epoxide reduction by salicylate

Salicylate antagonizes the vitamin K-dependent biosynthesis of clotting factors in the rat and produces an elevation of the ratio of vitamin K epoxide to vitamin K in the liver. Vitamin K epoxide is reduced to vitamin K by a vitamin K epoxide reductase, and 1 mM salicylate was required to cause a 50% inhibition of the dithiothreitol-dependent in-vitro reduction of vitamin K epoxide by this enzyme. This enzyme was, however, inhibited 50% by as little as 70-80 μM salicylate when reducing equivalents for the reaction were furnished by endogenous cytosolic reductants. This effect on the cytosolic reductant supply was shown to be unrelated to a previously demonstrated inhibition of DT-diaphorase by salicylate. The concentrations of salicylate at which significant inhibitory effects are exerted in-vitro (50-100 μM) are below the 200 μM levels observed in the liver of rats given an anticoagulating dose of salicylate.

Improved synthesis of vitamin K1

With (E/Z)-isomeric phytyl halides as side-chain materials, vitamin K1 is synthesized via a Diels-Alder reaction to activate the free bridgehead hydrogen of 3 for the alkylation and a retro-Diels-Alder reaction to eliminate cyclopentadiene from 2 in a high yield, in which the configuration of the double bond in the phytyl side-chain is retained.

A Convenient One-flask Synthesis of Vitamin K

A facile synthesis of highly pure (E)-form vitamins K1 and K2 by the reaction of 3-substituted isobenzofuranones 2 with vinylic sulfones 1 in one flask is described.