Phylloquinone oxide

Base Information

• Chemical Name: Phylloquinone oxide
• CAS No.: 25486-55-9
• Molecular Formula: C31H46O3
• Molecular Weight: 466.704
• European Community (EC) Number: 247-022-9
• ChEMBL ID: CHEMBL299632
• DSSTox Substance ID: DTXSID80904572
• Nikkaji Number: J16.897A,J972.205J
• Mol file: 25486-55-9.mol

Synonyms:phylloquinone epoxide;phylloquinone oxide;vitamin K epoxide;vitamin K(1) oxide;vitamin K1 2,3-epoxide;vitamin K1 epoxide;vitamin K1 oxide

Chemical Property of Phylloquinone oxide

Chemical Property:

• Vapor Pressure: 1.28E-12mmHg at 25°C
• Refractive Index: 1.523
• Boiling Point: 561.1 °C at 760 mmHg
• Flash Point: 233.8 °C
• PSA: 46.67000
• Density: 1.019g/cm³
• LogP: 8.36880
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• XLogP3: 10.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 466.34469533
• Heavy Atom Count: 34
• Complexity: 737

Purity/Quality:

VITAMIN K1 2,3-EPOXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)CCCC(C)CCCC(=CCC12C(=O)C3=CC=CC=C3C(=O)C1(O2)C)C
• Isomeric SMILES: CC(C)CCCC(C)CCCC(C)CCC/C(=C/CC12C(=O)C3=CC=CC=C3C(=O)C1(O2)C)/C
• Description: Vitamin K is a dietary nutrient essential for the normal biosynthesis of factors that are required for blood clotting. It has also been shown to inhibit cell growth. Vitamin K1 2,3-epoxide is the inactive metabolite of vitamin K1. During clotting, vitamin K1 is converted to this epoxide form and then rapidly reduced back to the vitamin by a microsomal epoxide reductase. This is referred to as the vitamin K epoxide cycle. Certain anticoagulants target clotting factor synthesis by inhibiting the recycling of vitamin K1 from the inactive epoxide.
• Uses: A metabolite of Vitamin K1 (V676080).

Technology Process of Phylloquinone oxide

There total 7 articles about Phylloquinone oxide 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: 68.0%

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) → vitamin K1 epoxide (25486-55-9,85954-59-2,85955-78-8)

Guidance literature:

With sodium hydroxide; (-)-N-benzylquininium chloride; dihydrogen peroxide; In toluene; at 40 ℃;

DOI:10.1021/jo00161a034

Reference yield: 28.0%

2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone (81818-54-4) → Vitamin K1 2,3-epoxide (25486-55-9)

Guidance literature:

With tert.-butylhydroperoxide; sodium hydroxide; β‐cyclodextrin; In N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1021/jo00310a018

Reference yield:

→ vitamin K epoxide (25486-55-9,85954-59-2,85955-78-8)

Guidance literature:

Vitamin K(1), KO2, 18-Krone-6;

DOI:10.1016/S0040-4039(01)93626-3

upstream raw materials:

2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone

trans-1,4-Dihydro-vitamin K₁⁽²⁰⁾

phytomenadione

vitamin K₁

Downstream raw materials:

2-methyl-3-(3,7,11,15-tetramethyl-hexadec-2-enyl)-[1,4]naphthoquinone

vitamin K₁

trans-1,4-Dihydro-vitamin K₁⁽²⁰⁾

2-Hydroxy-2-methyl-3-phytyl-2,3-dihydro-1,4-naphthoquinone

Refernces

• 1、 -. "Immunomodulating compositions for treatment of immune system disorders". . . Retrieved 2008/06/13.
• 2、 Colonna,Manfredi,Annuziata,Gaggero,Casella. "Biomimetic asymmetric synthesis. Enantioselective Weitz-Scheffer epoxidation of vitamin K3 and analogues in the presence of cyclodextrins". . p. 5862 - 5866. Retrieved 2007/10/02.