39776-45-9

Usage

InChI:InChI=1/C31H42O2/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/h7-8,12,14,16,18-20,32-33H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+

Upstream product

• 863-61-6 menatetrenone 
• 53254-60-7 3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene 
• 1113-21-9 (6E,10E)-geranyllinalool 
• 94828-14-5 1,4-Bis-benzyloxy-2-((2E,6E)-8-bromo-3,7-dimethyl-octa-2,6-dienyl)-3-methyl-naphthalene 
• 94828-06-5 (2E,6E)-8-(1,4-Bis-benzyloxy-3-methyl-naphthalen-2-yl)-2,6-dimethyl-octa-2,6-dien-1-ol 
• 94828-04-3 1,4-Bis-benzyloxy-2-((E)-4-bromo-3-methyl-but-2-enyl)-3-methyl-naphthalene 
• 94828-30-5 (E)-4-(1,4-Bis-benzyloxy-3-methyl-naphthalen-2-yl)-2-methyl-but-2-en-1-ol 
• 68690-45-9 (2E,6E)-3,7,11-trimethyl-1-(p-tolylsulfonyl)dodeca-2,6,10-triene 
• 94828-02-1 2-(9'-p-tosyl-tetraprenyl)-3-methyl-1,4-dibenzyloxynaphthalene 
• 94828-03-2 2-(5'-p-tosyl-tetraprenyl)-3-methyl-1,4-dibenzyloxynaphthalene 

Downstream Products

• 863-61-6 menatetrenone 

Relevant academic research and scientific papers

Method for producing quinone compound

A method for producing menatetrenone that does not have a deleterious influence on the environment, that is safe even when applied to large-scale production, and that is also simple to operate, wherein a compound represented by the following formula (1) is produced by treating with an oxygen source, and without the addition of an additive other than water or aqueous sodium chloride solution, a reaction solution consisting essentially of a solution of a compound represented by the following formula (2) dissolved in a solvent:

Vitamin K prodrugs: 1. Synthesis of amino acid esters of menahydroquinone-4 and enzymatic reconversion to an active form

The efficacy and toxicity of vitamin K depends on the pathway and the extent of enzymatic reductive activation to vitamin K hydroquinone, which is an essential cofactor for the synthesis of clotting factors. Parenteral use of vitamin K is impaired by its water insolubility. With the aim to improve delivery problems associated with menahydroquinone-4 (MKH, 2), an active form of menaquinone-4, N,N-dimethylglycine esters of 2 (1-mono, 4-mono, and 1,4-bis) were synthesized and assessed as potential water-soluble prodrugs for parenteral use, The esters can deliver the hydroquinone to its active site without a quinone reductive activation step. The hydrochloride salts of the esters were found to be quite soluble in water. The hydrolysis of the esters in 20% rat liver homogenate 9000 x g supernatant, rat plasma and phosphate buffer, pH 7.4, at 37°C was kinetically studied in the presence and absence of an esterase inhibitor. The hydrolysis was catalyzed by esterases located in the rat liver and rat plasma and quantitatively yielded 2. These results suggest that esterification of 2 with N,N-dimethylglycine is a promising way for obtaining water-soluble prodrug forms of 2. Based on the high susceptibility to liver esterase, the esters are potential prodrugs for achieving the site-specific delivery of 2.

Synthetic Studies on Isoprenoidquinones. II. Syntheses of Ubiquinone-10, Phylloquinone, and Menaquinone-4 by a Chain-Extending Method Utilizing Terminally Functionalized Isoprenoidhydroquinones

Physiologically active polyisopreoidquinones, ubiquinone-10 (coenzyme Q10), phylloquinone (vitamin K1), and menaquinone-4 (vitamin K2(20)) were synthesized by a chain-extending method utilizing protected hydroquinones with the omega-hydroxyprenyl or omega-hydroxygeranyl side chain.Conditions for reductive desulfurization subsequent to allylic homologation was investigated. Keywords - polyisoprenoidquinone synthesis; ubiquinone-10; phylloquinone; menaquinone-4; chain-extending method; sulfone coupling; reductive desulfurization