Methyl gamma-linolenate

Base Information

• Chemical Name: Methyl gamma-linolenate
• CAS No.: 16326-32-2
• Molecular Formula: C19H32 O2
• Molecular Weight: 292.462
• Hs Code.: 2916190090
• DSSTox Substance ID: DTXSID901344802
• Nikkaji Number: J187.513B
• Wikidata: Q63409034
• Mol file: 16326-32-2.mol

Synonyms:16326-32-2;Methyl gamma-linolenate;gamma-Linolenic acid methyl ester;methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate;methyl GLA;(6Z,9Z,12Z)-Methyl octadeca-6,9,12-trienoate;Methyl (Z,Z,Z)-6,9,12-octadecatrienoate;6,9,12-Octadecatrienoic acid, methyl ester, (6Z,9Z,12Z)-;all-cis-6,9,12-Octadecatrienoic acid methyl ester;6,9,12-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-;Methyl-gama-linolenate;Methyl gamma -Linolenate;SCHEMBL7170526;CHEBI:144354;DTXSID901344802;gamma.-Linolenic acid methyl ester;HMS3649L20;.gamma.-Linolenic acid, methyl ester;AKOS025311588;CS-W009992;HY-W009276;(c)(3/4)-Linolenic Acid methyl ester;Methyl gamma-linolenate, >=99% (GC);AC-33778;AS-70117;BP-29876;C18:3 (all cis-6,9,12) methyl ester;Methyl 6(Z),9(Z),12(Z)-Octadecatrienoate;(6Z,9Z,12Z)-Methyloctadeca-6,9,12-trienoate;SR-01000946739;SR-01000946739-1;Q63409034;(6Z,9Z,12Z)-6,9,12-octadecatrienoic acid methyl ester;(Z,Z,Z)-6,9,12-OCTADECATRIENOIC ACID METHYL ESTER;C19H32O2 (cis-octadeca-6,9,12-trienoic acid methyl ester)

Chemical Property of Methyl gamma-linolenate

Chemical Property:

• Vapor Pressure: 3.81E-06mmHg at 25°C
• Refractive Index: n20/D 1.476(lit.)
• Boiling Point: 385.4°Cat760mmHg
• Flash Point: 101.5°C
• PSA: 26.30000
• Density: 0.895g/cm³
• LogP: 5.74890
• Storage Temp.: −20°C
• Solubility.: ≤100mg/ml in DMSO;100mg/ml in dimethyl formamide
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 292.240230259
• Heavy Atom Count: 21
• Complexity: 314

Purity/Quality:

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

γ-LinolenicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCCCCC(=O)OC
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OC
• Description: Polyunsaturated fatty acids (PUFAs) are essential nutrients that show distinct deficiency syndromes when not present in adequate amounts in the diet. γ-Linolenic Acid methyl ester (Methyl GLA) is an esterified version of the free acid which is less water soluble but more amenable for the formulation of GLA-containing diets and dietary supplements. 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 of 1 μM. GLA produces 53% inhibition at a 1 mg/kg dose in an in vivo model of LTB4-induced bronchoconstriction.
• Uses: Methyl γ-linolenate may be used as an analytical standard for the determination of aldehydes such as pentanal and hexanal via peroxidation, further analyzed by gas chromatography technique. It may also be used as an analytical reference standard for the quantification of the analyte in serum lipid extract and Arthrospira (Spirulina) platensis using the gas-chromatography technique.

Technology Process of Methyl gamma-linolenate

There total 16 articles about Methyl 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: 65.0%

Octadeca-6,9,12-triinsaeure-methylester (16326-31-1) → methyl linoleate (16326-32-2)

Guidance literature:

With hydrogen; ethylenediamine; P-2 Ni; In ethanol;

DOI:10.1055/s-1998-2104

Reference yield:

methanol (67-56-1) → methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) + methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) + methyl linoleate (16326-32-2) + methyl arachidonate (2566-89-4) + (Z)-9-hexadecenoic acid methyl ester (1120-25-8,3913-63-1) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + (11Z)-11-icosenoic acid methyl ester (2390-09-2,3946-08-5) + methyl linolenate (301-00-8) + methyl n-dodecanoate (111-82-0) + methyl myristoate (124-10-7) + pentadecanoic acid methyl ester (7132-64-1) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) + (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) + cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester (13487-42-8) + myristoleic acid methyl ester (56219-06-8) + cis,trans-9,11-methyloctadecadienoate (35042-75-2)

Guidance literature:

With potassium hydroxide; water; In methanol; at 55 ℃; for 1.5h;

methanol; With sulfuric acid; In water; at 20 - 55 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

methanol (67-56-1) + sodium methylate (124-41-4) → methyl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate (108698-02-8) + methyl vaccenate (1937-63-9,52380-33-3,6198-58-9) + methyl linoleate (16326-32-2) + methyl arachidonate (2566-89-4) + (Z)-9-hexadecenoic acid methyl ester (1120-25-8,3913-63-1) + Methyl oleate (112-62-9) + Methyl linoleate (112-63-0) + (11Z)-11-icosenoic acid methyl ester (2390-09-2,3946-08-5) + methyl linolenate (301-00-8) + methyl n-dodecanoate (111-82-0) + methyl myristoate (124-10-7) + pentadecanoic acid methyl ester (7132-64-1) + hexadecanoic acid methyl ester (112-39-0) + methyl margarate (1731-92-6) + Methyl stearate (112-61-8) + methyl arachidate (1120-28-1) + behenic acid methyl ester (929-77-1) + all-cis-8,11,14-eicosatrienoic acid methyl ester (21061-10-9) + (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-icosapentaenoic acid methyl ester (2734-47-6) + cis,cis,cis,cis-Docosa-7,10,13,16-tetraensaeuremethylester (13487-42-8) + myristoleic acid methyl ester (56219-06-8) + cis,trans-9,11-methyloctadecadienoate (35042-75-2)

Guidance literature:

at 55 ℃; for 1.5h; Product distribution / selectivity;

upstream raw materials:

all-cis-6,9,12-octadecatrienoic acid

Octadeca-6,9,12-triinsaeure-methylester

diazomethane

5-bromopentanoic acid

Downstream raw materials:

all-cis-6,9,12-octadecatrienoic acid

Refernces

• 1、 Harada, Ken-Ichi,Suomalainen, Mette,Uchida, Hideaki,Masui, Hiroaki,Ohmura, Kuniyo,Kiviranta, Jari,Niku-Paavola, Marja-Leena,Ikemoto, Takaya. "Insecticidal compounds against mosquito larvae from Oscillatoria agardhii strain 27". . p. 114 - 119. Retrieved 2007/10/03.