9Z,11E,13E-Octadecatrienoic Acid methyl ester - ≥98%, 10mg/ml in ethanol , CAS No.4175-47-7

CAS: 4175-47-7 Cat. No.: Z342825 Molecular Weight: 292.5 PubChem CID: 21718552

GRADE & PURITY ≥98%, 10mg/ml in ethanol

Synonyms

9(Z),11(E),13(E)-Octadecatrienoic acid methyl ester | 9Z,11E,13E-Octadecatrienoic Acid methyl ester | METHYL 9-CIS,11,13-TRANS-OCTADECATRIENOATE | HMS3650A18 | SCHEMBL16869366 | ELEOSTEARIC ACID, METHYL ESTER | Q27259120 | SR-01000946261-1 | Methyl 9(Z),1

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

9Z,11E,13E-octadecatrienoic acid (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ.In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 µM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 µM for different isoforms of the enzymes. α-ESA methyl ester is a neutral, more lipid soluble form of the free acid.

Specifications

Synonyms

9(Z), 11(E), 13(E)-Octadecatrienoic acid methyl ester | 9Z, 11E, 13E-Octadecatrienoic Acid methyl ester | METHYL 9-CIS, 11, 13-TRANS-OCTADECATRIENOATE | HMS3650A18 | SCHEMBL16869366 | ELEOSTEARIC ACID, METHYL ESTER | Q27259120 | SR-01000946261-1 | Methyl 9(Z), 1

Specifications & Purity

≥98%, 10mg/ml in ethanol

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

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

Note

Packaging specifications based on solute content

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCC=CC=CC=CCCCCCCCC(=O)OC
• IUPAC Name: methyl (9Z,11E,13E)-octadeca-9,11,13-trienoate
• InChIKey: KOJYENXGDXRGDK-ZUGARUELSA-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/h6-11H,3-5,12-18H2,1-2H3/b7-6+,9-8+,11-10-
• Isomeric SMILES: CCCC/C=C/C=C/C=C\CCCCCCCC(=O)OC
• PubChem CID: 21718552
• Molecular Weight: 292.5

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

• Boil Point(°C): 78° C
• Molecular Weight: 292.500 g/mol
• XLogP3: 6.700
• 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. Jinrui Guo, Yaozong Duan, Fashe Li, Huicong Zhang, Fangguan Tan, Xinhua Qian, Hua Wang.  (2025)  Effects of fuel oxidation on the emission characteristics and formation mechanism of aldehydes from biodiesel combustion: Experimental and simulation analysis.  JOURNAL OF THE ENERGY INSTITUTE,      [PMID:] [10.1016/j.joei.2025.102289]