Phytonadiol

Base Information

• Chemical Name: Phytonadiol
• CAS No.: 572-96-3
• Molecular Formula: C31H48O2
• Molecular Weight: 452.721
• European Community (EC) Number: 209-344-8
• UNII: O8GP21P496
• DSSTox Substance ID: DTXSID90409306
• Metabolomics Workbench ID: 29112
• Nikkaji Number: J188.437I
• Wikidata: Q27089149
• Mol file: 572-96-3.mol

Synonyms:dihydrovitamin K1;dihydroxyvitamin K;reduced vitamin K;reduced vitamin K1;vitamin K1 hydroquinone

Chemical Property of Phytonadiol

Chemical Property:

• Vapor Pressure: 1.79E-14mmHg at 25°C
• Melting Point: 96-97 °C
• Refractive Index: 1.543
• Boiling Point: 589.1 °C at 760 mmHg
• PKA: 10.48±0.50(Predicted)
• Flash Point: 239.1 °C
• PSA: 40.46000
• Density: 0.981
• LogP: 9.48730
• XLogP3: 11.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 452.365430770
• Heavy Atom Count: 33
• Complexity: 553

Purity/Quality:

99% ^*data from raw suppliers

Dihydrovitamin K1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=CC=CC=C2C(=C1CC=C(C)CCCC(C)CCCC(C)CCCC(C)C)O)O
• Isomeric SMILES: CC1=C(C2=CC=CC=C2C(=C1C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O)O
• Uses: A metabolite of Vitamin K1

Technology Process of Phytonadiol

There total 5 articles about Phytonadiol 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:

phytomenadione (84-80-0) → 2-methyl-3-phytyl-1,4-naphthalenediol (572-96-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; di-isopropyl ether; for 0.166667h;

DOI:10.1248/bpb.22.1347

Reference yield:

2-methyl-1,4-naphthohydroquinone (481-85-6) + phytol (150-86-7,844467-91-0) → 2-methyl-3-phytyl-1,4-naphthalenediol (572-96-3)

Guidance literature:

With 1,4-dioxane; oxalic acid; at 75 ℃;

DOI:10.1021/ja01865a022

Reference yield:

menadione (58-27-5,34524-96-4) → 2-methyl-3-phytyl-1,4-naphthalenediol (572-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium dithionite / diethyl ether; Petroleum ether / 4 h

2: samarium(III) trifluoromethanesulfonate; acetic acid / Petroleum ether / 4 h / Inert atmosphere

With sodium dithionite; acetic acid; samarium(III) trifluoromethanesulfonate; In diethyl ether; Petroleum ether;

upstream raw materials:

2-methyl-1,4-naphthohydroquinone

phytol

1,4-dioxane

oxalic acid

Downstream raw materials:

phytomenadione

Refernces

• 1、 Takata, Jiro,Karube, Yoshiharu,Matsunaga, Kazuhisa,Hanada, Mitsunobu,Hidaka, Ryoji,Matsushima, Yoshikazu. "Prodrugs for systemic bioreductive activation-independent delivery of phyllohydroquinone, an active form of phylloquinone (vitamin K1) 1: Preparation and in vitro evaluation". . p. 1347 - 1354. Retrieved 1999.
• 2、 -. "Method for synthesizing vitamin K1". Paragraph 0023; 0024; 0026. . Retrieved 2017/02/23.