Octadeca-9,12,15-trienoic acid

Base Information

• Chemical Name: Octadeca-9,12,15-trienoic acid
• CAS No.: 463-40-1
• Molecular Formula: C18H30O2
• Molecular Weight: 278.435
• Hs Code.: DERIVATION
• European Community (EC) Number: 217-792-0
• UNII: PO45E3L8YU
• DSSTox Substance ID: DTXSID401315640
• Nikkaji Number: J17.685K,J199.777G,J464.118C
• Wikidata: Q27286664
• Metabolomics Workbench ID: 583
• Mol file: 463-40-1.mol

Synonyms:Elaidolinolenic acid;(9E,12E,15E)-octadeca-9,12,15-trienoic acid;linolenelaidic acid;Octadeca-9,12,15-trienoic acid;28290-79-1;1955-33-5;9,12,15-Octadecatrienoic acid;UNII-PO45E3L8YU;PO45E3L8YU;(9E,12E,15E)-9,12,15-Octadecatrienoic acid;9E,12E,15E-octadecatrienoic acid;EINECS 217-792-0;delta9,12,15-Octadecatrienoic acid;(E,E,E)-9,12,15-Octadecatrienoic acid;9,12,15-Octadecatrienoic acid, (E,E,E)-;trans-9, trans-12, trans-15-octadecatrienoic acid;C18:3n-3,6,9;linolensaure;9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-;SCHEMBL46586;CCRIS 7126;CHEBI:92583;CHEBI:165492;DTOSIQBPPRVQHS-IUQGRGSQSA-N;DTXSID401315640;BBL027460;LMFA01030153;STK801963;AKOS015955691;LS-1275;cis-9,cis-12,cis-15 Octadecadienoic acid;LS-102392;(9E,12E,15E)-9,12,15-Octadecatrienoate;(9E,12Z,15E)-9,12,15-Octadecatrienoic acid;(ALL TRANS)-9,12,15-OCTADECATRIENOIC ACID;9,12,15-Octadecatrienoic acid, (9E,12E,15E)-;PREVENTION 1 (LINOLENIC ACID)(PREVENTION 1);Q27286664

Chemical Property of Octadeca-9,12,15-trienoic acid

Chemical Property:

• Appearance/Colour: clear light yellow to yellow liquid
• Vapor Pressure: 4.24E-09mmHg at 25°C
• Melting Point: -11 °C(lit.)
• Refractive Index: 1.479 - 1.481
• Boiling Point: 443.376 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 275.733 °C
• PSA: 37.30000
• Density: 0.925 g/cm³
• LogP: 5.66050
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: INSOLUBLE
• 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:

90% up, 98% up ^*data from raw suppliers

Linolenic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCCCCCCCC(=O)O
• Isomeric SMILES: CC/C=C/C/C=C/C/C=C/CCCCCCCC(=O)O
• Uses: Linolenic acid has been used:to assess the total antioxidative activity of serum and bacteriain palleroni chamber assayto prepare free fatty acid mixture An essential fatty acid. Occurs as the glyceride in most drying oils. Nutrient. linolenic acid is also known as alpha-linolenic acid; omega-3. An essential fatty acid found in most drying oils. It is slightly irritating to the mucous membranes. It may be used in a cosmetic preparation for any of the following broad uses: anti-static, cleansing, emollient, skin-conditioning, and surfactant properties.

Technology Process of Octadeca-9,12,15-trienoic acid

There total 38 articles about Octadeca-9,12,15-trienoic 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:

methyl linolenate

cis,cis,cis-9,12,15-octadecatrienoyl chloride

9,12, 15-octadecatrienoic acid ethyl ester

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

Refernces

• 1、 Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.. "A nine carbon homologating system for skip-conjugated polyenes". . p. 34 - 42. Retrieved 2014/07/08.
• 2、 Cheng, Jin-Tang,Li, Yan,He, Juan,Li, Xing-Yao,Wu, Xing-De,Shao, Li-Dong,Dong, Liao-Bin,Deng, Xu,Gao, Xiu,Peng, Li-Yan,Cheng, Xiao,Zhao, Qin-Shi. "Three new sucrose fatty acid esters from Equisetum hiemale L.". experimental part. p. 1158 - 1163. Retrieved 2012/09/22.