Ethyl gamma-linolenate

Base Information

• Chemical Name: Ethyl gamma-linolenate
• CAS No.: 31450-14-3
• Molecular Formula: C₂₀H₃₄O₂
• Molecular Weight: 306.489
• UNII: Z2942E0NCT
• Nikkaji Number: J647.859J
• Wikidata: Q27294903
• Mol file: 31450-14-3.mol

Synonyms:31450-14-3;gamma-Linolenic acid ethyl ester;Ethyl gamma-linolenate;Ethyl gamma-linolenic acid;Ethyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate;Gamma-linolenicacidethylester;UNII-Z2942E0NCT;Z2942E0NCT;gamma-Linolenic acid, ethyl ester;.gamma.-Linolenic acid ethyl ester;6,9,12-Octadecatrienoic acid, ethyl ester, (6Z,9Z,12Z)-;??-Linolenic acid ethyl ester;ETHYL .GAMMA.-LINOLENATE;SCHEMBL17871051;CHEBI:183738;MJLYTDAIYLGSRZ-ORZIMQNZSA-N;ETHYL .GAMMA.-LINOLENIC ACID;AKOS040758537;AC-33777;.GAMMA.-LINOLENIC ACID, ETHYL ESTER;HY-108396;CS-0028566;6Z,9Z,12Z-Octadecatrienoic acid, ethyl ester;cis-6,cis-9,cis-12 Octadecadienoic acid ethyl ester;Q27294903

Chemical Property of Ethyl gamma-linolenate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.475
• Boiling Point: 390.575oC at 760 mmHg
• Flash Point: 100.751oC
• PSA: 26.30000
• Density: 0.894g/cm3
• LogP: 6.13900
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (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:

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

γ-LinolenicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCCCCC(=O)OCC
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OCC
• Description: γ-Linolenic acid (GLA) is an ω-6 fatty acid which can be elongated to arachidonic acid for endogenous eicosanoid synthesis. It is a weak leukotriene B4 (LTB4) receptor antagonist, inhibiting [3H]-LTB4 binding to porcine neutrophil membranes with a Ki value of 1 μM. GLA produces 53% inhibition at a 1 mg/kg dose in an in vivo model of LTB4-induced bronchoconstriction. GLA ethyl ester is an esterified version of the free acid which is less water soluble but more amenable for the formulation of GLA-containing diets.
• Uses: γ-Linolenic Acid Ethyl Ester is used in biological studies for neoplasm inhibition of cultured carcinoma cells of human breast. This analog is also used in the evaluation of hypocholesterolemic activity in rats by comparing it with γ-Linolenic Acid (L467660).

Technology Process of Ethyl gamma-linolenate

There total 2 articles about Ethyl gamma-linolenate 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:

BGC-20-0134 (847019-77-6) + ethanol (64-17-5) → 2-γ-linolenic acid monoglyceride + C21H36O4 (157500-74-8) + decanoic acid ethyl ester (110-38-3) + cis-6,cis-9,cis-12-octadecatrienoic acid ethyl ester (31450-14-3)

Guidance literature:

lipase acrylic resin; at 35 - 40 ℃; for 3h; acrylic resin Enzymatic reaction;

Reference yield:

cis-6,cis-9-octadecadienoic acid ethyl ester (959510-75-9) → cis-6,cis-9,cis-12-octadecatrienoic acid ethyl ester (31450-14-3)

Guidance literature:

With Trichoderma sp. 1-OH-2-3; In water; at 28 ℃; for 168h; pH=6; Microbiological reaction;

DOI:10.1007/s11746-008-1339-2

upstream raw materials:

BGC-20-0134

ethanol

cis-6,cis-9-octadecadienoic acid ethyl ester

Refernces

• 1、 -. "CYTOKINE MODULATORS USING CYCLIC GLYCERIDES OF ESSENTIAL POLYUNSATURATED FATTY ACIDS". Page/Page column 17. . Retrieved 2008/06/13.