Oleyl alcohol

Base Information

• Chemical Name: Oleyl alcohol
• CAS No.: 143-28-2
• Deprecated CAS: 8014-60-6,8029-00-3,8038-59-3,84286-21-5,8029-00-3,8038-59-3,84286-21-5
• Molecular Formula: C18H36O
• Molecular Weight: 268.483
• Hs Code.: 29052990
• European Community (EC) Number: 205-597-3,209-791-9
• NSC Number: 10999
• UNII: 172F2WN8DV
• DSSTox Substance ID: DTXSID0022010
• Nikkaji Number: J5.818A
• Wikipedia: Oleyl_alcohol
• Wikidata: Q7086489
• NCI Thesaurus Code: C76721
• RXCUI: 1310603
• Metabolomics Workbench ID: 3303
• ChEMBL ID: CHEMBL2105350
• Mol file: 143-28-2.mol

Synonyms:(Z)-octadec-9-enol;cis-9-octadecen-1-ol;Oleol;oleyl alcohol;oleyl alcohol, (Z)-isomer

Chemical Property of Oleyl alcohol

Chemical Property:

• Appearance/Colour: Colourless to light yellow liquid
• Vapor Pressure: 1E-05mmHg at 25°C
• Melting Point: 5 °C
• Refractive Index: n20/D 1.46(lit.)
• Boiling Point: 333 °C at 760 mmHg
• PKA: 15.20±0.10(Predicted)
• Flash Point: 120.7 °C
• PSA: 20.23000
• Density: 0.847 g/cm³
• LogP: 6.01620
• Storage Temp.: −20°C
• Solubility.: Soluble in ethanol (95%), and ether; practically insoluble in water.
• Water Solubility.: Miscible with alcohol and ether. Slightly miscible with carbon tetrachloride. Immiscible with water.
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 15
• Exact Mass: 268.276615768
• Heavy Atom Count: 19
• Complexity: 175

Purity/Quality:

90%,98% ^*data from raw suppliers

(9Z)-9-Octadecen-1-ol,85% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Emulsifiers/Surfactants
• Canonical SMILES: CCCCCCCCC=CCCCCCCCCO
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCO
• Uses: Oleyl alcohol is used in softening and lubrication of textile fabrics, and in the production of carbon paper, stencil paper, and printing ink. It finds application in cosmetic products viz skin creams and lotions as a thickner, hair conditioners and hair coating shampoos. It is utilized as an antifoaming agent and cutting lubricant, as the precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents. It plays a vital role in various formulations for drug delivery. oleyl alcohol is an emollient, solvent, viscosity-increasing agent, and carrier employed in a wide variety of cosmetic formulations including makeup, skin care, and hand and body preparations. oleyl alcohol is an unsaturated fatty alcohol found in fish oils and can also be produced synthetically. According to some sources, it is comedogenic and has a mild irritancy potential. Chiefly in the manufacture of its sulfuric esters which are detergents and wetting agents, as an antifoam agent; metal cutting lubricant; in carbon paper, stencil paper, printing ink; as a plasticizer; for softening and lubricating textile fabrics; carrier for medicaments.

Technology Process of Oleyl alcohol

There total 66 articles about Oleyl alcohol 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: 93.0%

trioleoylglycerol (122-32-7) → oleoyl alcohol (143-28-2,593-47-5,84286-21-5) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; water; at 70 ℃; for 4h;

Reference yield: 73.62%

vernonia oil methyl esters → Linoleyl alcohol (506-43-4) + oleoyl alcohol (143-28-2,593-47-5,84286-21-5) + 1-Hexadecanol (36653-82-4,124-29-8) + cis-12,13-epoxy-cis-9-octadecenol

Guidance literature:

With lithium aluminium tetrahydride; In hexane; at 20 ℃; for 2h; Further byproducts given;

DOI:10.1007/s11746-000-0139-9

Reference yield:

cis-Octadecenoic acid (112-80-1,2027-47-6) → oleoyl alcohol (143-28-2,593-47-5,84286-21-5) + Oleic aldehyde (2423-10-1)

Guidance literature:

With (2-methyl-4-phenyl-1-oxabuta-1,3-diene)tricarbonyliron⁽⁰⁾; 1,1,3,3-tetramethyldisilazane; In toluene; at 50 ℃; for 48h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c2cc35727e

upstream raw materials:

oleic acid ethyl ester

Elaidic Acid

octadec-9-enoic acid methyl ester

oleic acid menthyl ester

Downstream raw materials:

(octadecen-(9c)-yl)-benzyl ether

oleyl acetate

3-Oleyloxy-3-phenyl-propionitril

4-Oleyloxy-butyronitril

Refernces

• 1、 El Asmar, Arlette,Gimello, Olinda,Morandi, Ga?lle,Le Cerf, Didier,Lapinte, Vincent,Burel, Fabrice. "Tuning the Thermo-Sensitivity of Micellar Systems through a Blending Approach". . p. 4307 - 4315. Retrieved 2016.
• 2、 Verba, G. G.,Abdukakharov, V. S.,Abduvakhabov, A. A.. "SYNTHESIS OF MUSCALURE - THE PHEROMONE OF Musca domestica". . p. 655 - 657. Retrieved 1985.
• 3、 Hamberg, Mats. "A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids". . p. 489 - 494. Retrieved 2021/04/19.
• 4、 -. "OLEIC ACID DERIVATIVES AS TREATMENTS FOR FRIEDREICH ATAXIA AND INHIBITORS OF FERROPTOSIS". . . Retrieved 2021/05/21.