9E,12Z,15Z-octadecatrienoic acid

Base Information

• Chemical Name: 9E,12Z,15Z-octadecatrienoic acid
• CAS No.: 21661-09-6
• Molecular Formula: C18H30O2
• Molecular Weight: 278.4296
• Nikkaji Number: J426.763J
• Wikidata: Q106040929
• Metabolomics Workbench ID: 767
• Mol file: 21661-09-6.mol

Synonyms:9E,12Z,15Z-octadecatrienoic acid;21661-10-9;21661-09-6;C18:3n-3,6,9;trans-alpha-linolenic acid;9,12,15-Octadecatrienoic acid, (E,Z,Z)-;(9E,12Z,15Z)-octadeca-9,12,15-trienoic acid;SCHEMBL12903692;CHEBI:165491;LMFA01030350;9,12,15-Octadecatrienoic acid, (Z,E,Z)-;18:3(9E,12Z,15Z)

Chemical Property of 9E,12Z,15Z-octadecatrienoic acid

Chemical Property:

• Vapor Pressure: 4.24E-09mmHg at 25°C
• Boiling Point: 443.4°Cat760mmHg
• Flash Point: 275.7°C
• Density: 0.924g/cm³
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 278.224580195
• Heavy Atom Count: 20
• Complexity: 301

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCCCCCCCC(=O)O
• Isomeric SMILES: CC/C=C\C/C=C\C/C=C/CCCCCCCC(=O)O

Technology Process of 9E,12Z,15Z-octadecatrienoic acid

There total 42 articles about 9E,12Z,15Z-octadecatrienoic acid 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%

methyl linolenate (301-00-8) → (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 18h; Ambient temperature;

DOI:10.1055/s-1995-3906

Reference yield: 75.0%

(3Z,6Z)-nona-3,6-dienal (21944-83-2) + (8-carboxyoctyl)triphenylphosphonium bromide (88462-46-8) → (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/j.chemphyslip.2014.04.005

Reference yield: 70.0%

(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid (R)-2-((7Z,10Z,13Z)-hexadeca-7,10,13-trienoyloxy)-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester → (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) + (7Z,10Z,13Z)-Hexadeca-7,10,13-trienoic acid (R)-2-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

Guidance literature:

With boric acid-borax buffer; Rhizopus arrhizus lipase XI; Triton X-100; at 38 ℃; for 1h; Yields of byproduct given;

DOI:10.1002/(SICI)1522-2675(19980909)81:9<1681::AID-HLCA1681>3.0.CO;2-4

upstream raw materials:

9,10,12,13,15,16-hexabromo-octadecanoic acid

ethanol

linoleic acid

(2S)-3-O-[α-D-galactopyranosyl-(1->6)-β-D-galactopyranosyl]-1-O-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]-sn-glycerol

Downstream raw materials:

1,3-Bis-linolenoyloxy-3-palmitoyloxy-propan

9,12, 15-octadecatrienoic acid ethyl ester

linolenic acid anilide

2.4-Dinitro-phenylhydrazon von Linolensaeure-(4-brom-phenacylester)