Methyl γ-linolenate - ≥98% , CAS No.16326-32-2

CAS: 16326-32-2 Cat. No.: M104529 Molecular Weight: 292.46 EC Number: 680-551-7

GRADE & PURITY ≥98%

Synonyms

methyl GLA | Methyl (Z,Z,Z)-6,9,12-octadecatrienoate | gamma-Linolenic acid methyl ester | methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate | (6Z,9Z,12Z)-Methyl octadeca-6,9,12-trienoate | Methyl gamma-linolenate | Fame 18:3n-6

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Application

Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Overview

γ-Linolenic Acid methyl ester (Methyl GLA) is an esterified version of γ-Linolenic Acid (GLA), which is an ω-6 fatty acid, serves as melanoma cell proliferation inhibitors. γ-Linolenic Acid methyl ester inhibits ADP-induced blood platelet aggregation and induces apoptosis.

Specifications

Synonyms

methyl GLA | Methyl (Z, Z, Z)-6, 9, 12-octadecatrienoate | gamma-Linolenic acid methyl ester | methyl (6Z, 9Z, 12Z)-octadeca-6, 9, 12-trienoate | (6Z, 9Z, 12Z)-Methyl octadeca-6, 9, 12-trienoate | Methyl gamma-linolenate | Fame 18:3n-6

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Methyl γ-linolenate (C18:6, 9, 12) differs from methyl α-linolenate (C18:9, 12, 15) in the positions of the double bonds. Methyl γ-linolenate may be used in nutritional studies regarding weight regain and as a possible tumor suppression agent.

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCC=CCC=CCC=CCCCCC(=O)OC
• IUPAC Name: methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
• InChIKey: JFRWATCOFCPIBM-JPFHKJGASA-N
• INCHI: 1S/C19H32O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19(20)21-2/h7-8,10-11,13-14H,3-6,9,12,15-18H2,1-2H3/b8-7-,11-10-,14-13-
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)OC
• WGK Germany: 3
• Molecular Weight: 292.46
• Reaxy-Rn: 27162437
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27162437&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Lineolic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Lineolic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Lineolic acids and derivatives
• Alternative Parents: Fatty acid methyl esters Methyl esters Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Octadecanoid - Fatty acid methyl ester - Fatty acid ester - Methyl ester - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: Light & Air & Heat sensitive
• Refractive Index: 1.476
• Flash Point(°C): 62℃
• Boil Point(°C): 162 °C/0.5 mmHg (lit.)
• Molecular Weight: 292.500 g/mol
• XLogP3: 6.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 292.24 Da
• Monoisotopic Mass: 292.24 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 314.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 3
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 3
• Covalently-Bonded Unit Count: 1

References

1. Jinghan Cui, Wenjie Yu, Qifang Sun, Qiuning Wang, Jinwang Li, Xiali Guo, Yanling Song, Yan Li, Liping Luo.  (2025)  Response of quality differences of winter wheat from different origins to meteorological factors based on metabolomics.  FOOD CHEMISTRY,      [PMID:41391413] [10.1016/j.foodchem.2025.147539]