84-81-1

Basic information

• Product Name: VITAMIN K2
• Synonyms: MENAQUINONE;MENAQUINONE 4;prenylmenaquinone-6;vitamin K2(30);Menaquinone 6;2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexenyl]-3-methyl-1,4-naphthalenedione;Farnoquinone;Menaquinone-K6
• CAS NO: 84-81-1
• Molecular Formula: C₄₁H₅₆O₂
• Molecular Weight: 444.65
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 84-81-1.mol

Chemical Properties

• Melting Point: 49-50 ºC
• Boiling Point: 673.3oC at 760 mmHg
• Flash Point: 240.7oC
• Appearance: /
• Density: 0.970
• Vapor Pressure: 5.49E-18mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: −20°C
• CAS DataBase Reference: VITAMIN K2(CAS DataBase Reference)
• NIST Chemistry Reference: VITAMIN K2(84-81-1)
• EPA Substance Registry System: VITAMIN K2(84-81-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: QL9279500
• Hazardous Substances Data: 84-81-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
VITAMIN K2 is used as a pharmaceutical agent for its anti-hemorrhagic properties and involvement in various physiological processes.
Used in Research Applications:
VITAMIN K2 is used as a research compound for studying the role of Menaquinones in membrane preparations of Campylobacter jejuni and Campylobacter fetus.

InChI:InChI=1/C41H56O2/c1-30(2)16-11-17-31(3)18-12-19-32(4)20-13-21-33(5)22-14-23-34(6)24-15-25-35(7)28-29-37-36(8)40(42)38-26-9-10-27-39(38)41(37)43/h9-10,16,18,20,22,24,26-28H,11-15,17,19,21,23,25,29H2,1-8H3/b31-18+,32-20+,33-22+,34-24+,35-28+

Upstream product

• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 1597486-86-6 phenylsulfonyl hexaprenyl bromide 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 74609-99-7 geranylfarnesyl-bromide 
• 37905-02-5 (2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate 
• 53772-33-1 2-bromo-3-methyl-1,4-dimethoxynaphthalene 
• 53772-19-3 1,4-dimethoxy-2-methylnaphthalene 
• 78-79-5 isoprene 
• 59277-17-7 1-(benzenesulfonyl)-2-methyl-4-chloro-2-butene 
• 73875-18-0 (2′E)-2-(3′-methyl-4′-phenylsulfonylbut-2′-enyl)-1,4-dimethoxy-3-methylnaphthalene 
• 146033-76-3 all-trans-pentaprenyl chloride 
• 22488-05-7 geranylfarnesol 
• 106-24-1 Geraniol 
• 56881-53-9 (E,E)-farnesyl phenylsulfone 

Downstream Products

• 5934-23-6 1,4-diacetoxy-2-(3,7,11,15,19,23-hexamethyl-tetracosa-2t,6t,10t,14t,18t,22-hexaenyl)-3-methyl-naphthalene 

Relevant articles and documents

PROCESS OF VITAMIN K2 DERIVATIVES PREPARATION

The invention relates to an improved process of vitamin K2 derivatives preparation via the alkylation of the menadione-cyclopentadiene adduct.

Synergistic factors ensue high expediency in the synthesis of menaquinone [K2] analogue MK-6: Application to access an efficient one-pot protocol to MK-9

Here we report a practical and efficient method for the synthesis of menaquinone vitamin (K2) analog MK-6 in all trans forms through “1 + 5 convergent synthetic approach” of pentaprenyl chloride with monoprenyl menadione derivative. In the synergistic factors, less efficient leaving group/more efficient nucleophile (Cl) in the substrate makes it more prominent reaction by eliminating all Sn2’ side reaction products. Further, the addition of acetic acid in the last step (desulfonation) of reaction sequence removes the limitations of the reactions in terms of cyclized side product (multiple reactions of pentaprenyl alcohol with Et3B), byproduct (Et3B, incendiary compound) formations and their interruption in the tricky purification processes. The utility of this method was further extended to find an efficient one-pot synthesis to MK-9 to the gram scale synthesis. This approach is economical and efficient and avoids the awkward chromatographic separation processes.