(9Z,12Z)-Octadeca-9,12-dien-1-ol

Base Information

• Chemical Name: (9Z,12Z)-Octadeca-9,12-dien-1-ol
• CAS No.: 506-43-4
• Molecular Formula: C18H34 O
• Molecular Weight: 266.467
• Hs Code.: 2905290000
• European Community (EC) Number: 208-038-1
• UNII: P4OX1289YW
• DSSTox Substance ID: DTXSID50881240
• Wikipedia: Linoleyl_alcohol
• Wikidata: Q6554721
• Metabolomics Workbench ID: 66532
• Mol file: 506-43-4.mol

Synonyms:9,12-octadecadien-1-ol;linoleyl alcohol;linoleyl alcohol, (E,E)-isomer;linoleyl alcohol, (Z,Z)-isomer

Chemical Property of (9Z,12Z)-Octadeca-9,12-dien-1-ol

Chemical Property:

• Melting Point: -5--2 °C
• Refractive Index: 1.4670 to 1.4710
• Boiling Point: 374°Cat760mmHg
• PKA: 15.20±0.10(Predicted)
• Flash Point: 124.1°C
• PSA: 20.23000
• Density: 0.858g/cm³
• LogP: 5.79220
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 14
• Exact Mass: 266.260965704
• Heavy Atom Count: 19
• Complexity: 206

Purity/Quality:

98%,99%, ^*data from raw suppliers

(9Z,?12Z)?-9,?12-?Octadecadien-?1-?ol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCCO
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCCO
• Uses: (9Z,?12Z)?-9,?12-?Octadecadien-?1-?ol is a linoleyl acid derivative and building block used in the synthesis of lipid-?based unsymmetrical O,?O-?dialkylphosphites. (9Z,?12Z)?-9,?12-?Octadecadien-?1-?ol has been synthesized by transfer hydrogenation using a ruthenium-based catalyst from its parent fatty acid.

Technology Process of (9Z,12Z)-Octadeca-9,12-dien-1-ol

There total 15 articles about (9Z,12Z)-Octadeca-9,12-dien-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: 98.0%

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → Linoleyl alcohol (506-43-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1021/acs.jmedchem.1c00085

Reference yield: 98.0%

Methyl linoleate (112-63-0) → Linoleyl alcohol (506-43-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 24h;

DOI:10.1021/acs.jmedchem.8b00734

Reference yield: 91.0%

18-methoxy-octadeca-6c,9c-diene (23405-45-0) → Linoleyl alcohol (506-43-4)

Guidance literature:

With 15-crown-5; boron tribromide; sodium iodide; In dichloromethane; at -30 ℃; for 2h;

DOI:10.1016/S0040-4039(01)82114-6

upstream raw materials:

Methyl linoleate

linoleic acid

ethyl (9Z,12Z)-9,12-octadecadienoate

18-methoxy-octadeca-6c,9c-diene

Downstream raw materials:

cholesteryl cis,cis-9',12'-octadecadienyl ether

(9Z,12Z)-9,12-Octadecadien-1-yl acetate

(Z,Z)-11,14-eicosadienoic acid

dilinoleyl ketone

Refernces

• 1、 Xia, Ying,Lu, Yongshang,Larock, Richard C.. "Ring-opening metathesis polymerization (ROMP) of norbornenyl-functionalized fatty alcohols". . p. 53 - 61. Retrieved 2010.
• 2、 Fernández Montoya, Deicy J.,Contreras Jordan, Luis A.,Moreno-Murillo, Bárbara,Silva-Gómez, Edelberto,Mayorga-Wandurraga, Humberto. "Enantiomeric synthesis of natural alkylglycerols and their antibacterial and antibiofilm activities". supporting information. p. 2544 - 2550. Retrieved 2019/11/13.
• 3、 -. "AMPHIPHILE PRODRUGS". Page/Page column 0184. . Retrieved 2019/06/12.