cis-9,10-Epoxyoctadecan-1-ol

Base Information

• Chemical Name: cis-9,10-Epoxyoctadecan-1-ol
• CAS No.: 13980-12-6
• Molecular Formula: C₁₈H₃₆O₂
• Molecular Weight: 284.483
• UNII: Z92214JL6R
• Nikkaji Number: J617.823E
• Wikidata: Q27295157
• Mol file: 13980-12-6.mol

Synonyms:cis-9,10-Epoxyoctadecan-1-ol;Oleyl alcohol epoxide, cis-;cis-9,10-Epoxystearyl alcohol;Oxiraneoctanol, 3-octyl-, cis-;9,10-Epoxy-1-octadecanol, cis-;13980-12-6;1-Octadecanol, 9,10-epoxy-, cis-;UNII-Z92214JL6R;Z92214JL6R;2-Oxiraneoctanol, 3-octyl-, (2R,3S)-rel-;8-[(2S,3R)-3-octyloxiran-2-yl]octan-1-ol;SCHEMBL7708022;cis-9,10-epoxy-1-octadecanol;Q27295157

Chemical Property of cis-9,10-Epoxyoctadecan-1-ol

Chemical Property:

• Melting Point: 52.6-53.5 °C
• Boiling Point: 362.2±10.0 °C(Predicted)
• PKA: 15.20±0.10(Predicted)
• PSA: 32.76000
• Density: 0.903±0.06 g/cm3(Predicted)
• LogP: 5.22740
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 284.271530387
• Heavy Atom Count: 20
• Complexity: 206

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCC1C(O1)CCCCCCCCO
• Isomeric SMILES: CCCCCCCC[C@@H]1[C@@H](O1)CCCCCCCCO

Technology Process of cis-9,10-Epoxyoctadecan-1-ol

There total 10 articles about cis-9,10-Epoxyoctadecan-1-ol 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: 65.0%

epoxidized methyl oleate (2566-91-8) → 8-(3-octyloxiran-2-yl)octane-1-ol (4482-22-8,13980-12-6,13980-13-7)

Guidance literature:

With n-butyllithium; poly(methylhydrosiloxane); ethylene-1,2-bis(tetrahydroindenyl)titanium dichloride; In tetrahydrofuran; hexane; for 1h; Ambient temperature;

DOI:10.1021/jo00094a056

Reference yield: 51.0%

oleoyl alcohol (143-28-2,593-47-5,84286-21-5) → 8-(3-octyloxiran-2-yl)octane-1-ol (4482-22-8,13980-12-6,13980-13-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 50 ℃; for 0.0833333h; Microwave irradiation; Cooling with ice;

DOI:10.1039/c3gc36710j

Reference yield:

oleoyl alcohol (143-28-2,593-47-5,84286-21-5) → cis-9,10-Epoxyoctadecan-1-ol (4482-22-8,13980-12-6,13980-13-7)

Guidance literature:

With peracetic acid;

DOI:10.1021/ja01219a018

upstream raw materials:

(E)-9-octadecen-1-ol

oleoyl alcohol

epoxidized methyl oleate

butanoic acid ethyl ester

Downstream raw materials:

(9SR,10SR)-octadecane-1,9,10-triol

Refernces

• 1、 Fuchs, Christopher,Schwab, Wilfried. "Epoxidation, hydroxylation and aromatization is catalyzed by a peroxygenase from Solanum lycopersicum". . p. 52 - 60. Retrieved 2013/10/22.
• 2、 Reding, Matthew T.,Buchwald, Stephen L.. "An Inexpensive Air-Stable Titanium-Based System for the Conversion of Esters to Primary Alcohols". . p. 7884 - 7890. Retrieved 2007/10/03.