vitamin K semiquinone radical

Base Information

• Chemical Name: vitamin K semiquinone radical
• CAS No.: 27696-10-2
• Molecular Formula: C₃₁H₄₆O₂
• Molecular Weight: 450.705
• Mol file: 27696-10-2.mol

Synonyms:1,4-Naphthalenedione,2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, radical ion(1-),[R-[R*,R*-(E)]]-; Phylloquinone, radical ion(1-) (8CI); Vitamin K1 radicalanion; Vitamin K1 radical ion(1-); Vitamin K1 semiquinone

Chemical Property of vitamin K semiquinone radical

Chemical Property:

• Boiling Point: 546.4°Cat760mmHg
• Flash Point: 200.4°C
• Density: 0.963g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of vitamin K semiquinone radical

There total 31 articles about vitamin K semiquinone radical which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

trans-1,4-Dihydro-vitamin K1(20) (16869-68-4) → vitamin K1 (84-80-0,16033-41-3,27696-10-2,79082-95-4,79082-96-5,79082-97-6,79083-00-4,81818-54-4,105017-37-6,132487-93-5,132487-94-6,132487-95-7)

Guidance literature:

With dihydrogen peroxide; (Bu₃SnO)2CrO₂ on charcoal; In ethanol; at 40 ℃; for 1.5h;

DOI:10.1246/cl.1986.2075

Reference yield: 56.0%

→ vitamin K1 (84-80-0,16033-41-3,27696-10-2,79082-95-4,79082-96-5,79082-97-6,79083-00-4,81818-54-4,105017-37-6,132487-93-5,132487-94-6,132487-95-7)

Guidance literature:

With magnesium sulfate; silver(l) oxide; In diethyl ether;

Reference yield:

2-Bromo-3-Methyl-1,1,4,4-tetramethoxy-1,4-dihydronaphthalene (64648-85-7) + (7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide (943232-38-0) → menadione (58-27-5,34524-96-4) + vitamin K1 (84-80-0,16033-41-3,27696-10-2,79082-95-4,79082-96-5,79082-97-6,79083-00-4,81818-54-4,105017-37-6,132487-93-5,132487-94-6,132487-95-7)

Guidance literature:

With hydrogenchloride; n-butyllithium; copper (I) iodide; dimethylsulfide; water; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo01291a002

upstream raw materials:

menadione

C₁₃H₂₆Sn

2-Bromo-3-Methyl-1,1,4,4-tetramethoxy-1,4-dihydronaphthalene

(7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide

Downstream raw materials:

vitamin K₁ chromenol

2-(3-hydroperoxy-3,7,11,15-tetramethyl-hexadec-1-en-t-yl)-3-methyl-[1,4]naphthoquinone

vitamin K₁ epoxide

6,10,14-Trimethyl-2-pentadecanon

Refernces

• 1、 Lipshutz, Bruce H.,Kim, Sung-Kyu,Mollard, Paul,Stevens, Kirk L.. "An expeditious route to CoQ(n), Vitamins K1 and K2, and related allylated para-quinones utilizing Ni(0) catalysis". . p. 1241 - 1253. Retrieved 2007/10/03.
• 2、 Naganathan, Sriram,Hershline, Roger,Ham, Seung Wook,Dowd, Paul. "The active site of vitamin K and the role of the vitamin K-dependent carboxylase". . p. 9831 - 9839. Retrieved 2007/10/02.