9,12,15-Octadecatrienoic acid ethyl ester

Base Information

• Chemical Name: 9,12,15-Octadecatrienoic acid ethyl ester
• CAS No.: 1191-41-9
• Molecular Formula: C20H34O2
• Molecular Weight: 306.489
• Hs Code.: 29161900
• European Community (EC) Number: 214-734-6
• Nikkaji Number: J1.244.482F
• Metabolomics Workbench ID: 123596
• ChEMBL ID: CHEMBL1527567
• Mol file: 1191-41-9.mol

Synonyms:ethyl linolenate;linolenic acid ethyl ester

Chemical Property of 9,12,15-Octadecatrienoic acid ethyl ester

Chemical Property:

• Appearance/Colour: clear colorless liquid
• Vapor Pressure: 8.35E-06mmHg at 25°C
• Melting Point: 166-168 °C1 mm Hg(lit.)
• Refractive Index: n20/D 1.468(lit.)
• Boiling Point: 374.44 °C at 760 mmHg
• Flash Point: 100.674 °C
• PSA: 26.30000
• Density: 0.894 g/cm³
• LogP: 6.13900
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 306.255880323
• Heavy Atom Count: 22
• Complexity: 327

Purity/Quality:

99% ^*data from raw suppliers

LinolenicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC=CCC=CCC=CCCCCCCCC(=O)OCC
• Isomeric SMILES: CC/C=C/C/C=C/C/C=C/CCCCCCCC(=O)OCC
• Description: α-Linolenic acid ethyl ester is an esterified form of α-linolenic acid (Item Nos. 90210 | 21910). It increases cyclin E levels and the activity of Cdk2/cyclin E, ERK, and JNK in hepatic stellate cells when used at a concentration of 50 μM. α-Linolenic acid ethyl ester (25 μg/ml) inhibits the growth of S. mutans, C. albicans, and P. gingivalis by 98, 72, and 92%, respectively, in vitro. It has been found in biodiesel produced from castor oil using ethanol. α-Linolenic acid ethyl ester has been used as a substrate in lipid peroxidation assays for antioxidant activity.
• Uses: An exogenous source of α-linolenic acid. ethyl linolenate is an emollient reportedly used in indoor tanning preparations. It is not very popular as it may pose rancidity problems. It may also be used as an ingredient to enhance the fragrance of a product. Linolenic Acid Ethyl Ester is the ethyl ester derivative of Linolenic Acid (L467650); an essential fatty acid that occurs mostly as the glyceride in most drying oils. Also a nutrient.

Technology Process of 9,12,15-Octadecatrienoic acid ethyl ester

There total 6 articles about 9,12,15-Octadecatrienoic acid ethyl ester 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: 99.0%

ethanol (64-17-5) + (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) + orthoformic acid triethyl ester (122-51-0) → ethyl linolenate (1191-41-9)

Guidance literature:

With immobilized Candida antarctica Lipase B; In neat (no solvent); at 60 ℃; for 4h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.04.009

Reference yield:

fatty acids from sewage scum; extract of + ethanol (64-17-5) → hydroxy fatty acid ethyl esters + oleic acid ethyl ester (111-62-6) + ethyl (9Z,12Z)-9,12-octadecadienoate (544-35-4) + ethyl linolenate (1191-41-9) + hexadecanoic acid ethyl ester (628-97-7) + ethyl heptadecanoate (14010-23-2) + stearic acid ethyl ester (111-61-5)

Guidance literature:

sulfuric acid; at 60 ℃; for 1h; Conversion of starting material;

Reference yield:

ethanol (64-17-5) + (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) + Diethyl carbonate (105-58-8,76619-83-5) → ethyl linolenate (1191-41-9)

Guidance literature:

With immobilized Candida antarctica Lipase B; In neat (no solvent); at 60 ℃; for 12h; Green chemistry; Enzymatic reaction;

DOI:10.1016/j.molcatb.2012.04.009

upstream raw materials:

ethanol

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

Diethyl carbonate

orthoformic acid triethyl ester

Downstream raw materials:

α-linolenoyl ethanolamide

(9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid

9,12, 15-octadecatrienoic acid ethyl ester

Benzyl-diethyl-((9Z,12Z,15Z)-octadeca-9,12,15-trienyl)-ammonium; chloride

Refernces

• 1、 Cirujano,Corma,Llabrés I Xamena. "Zirconium-containing metal organic frameworks as solid acid catalysts for the esterification of free fatty acids: Synthesis of biodiesel and other compounds of interest". . p. 213 - 220. Retrieved 2015/02/19.
• 2、 -. "Compositions and methods of omega polyunsaturated fatty acids for the treatment of oral diseases". Page/Page column 2-3. . Retrieved 2011/05/05.