9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester - CAS 42021-86-3

9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester (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 ethyl ester is a neutral, more lipid soluble form of the free acid.

Catalog Number: R021630

CAS Number: 42021-86-3

PubChem Substance ID:355140914

Molecular Formula: C20H34O2

Molecular Weight:306.49

Purity: ≥95%

* For research use only. Not for human or veterinary use.

Synonym

Synonymsα-ESA ethyl ester;Ethyl α-eleostearate

Property

Molecular Formula: C20H34O2
Molecular Weight306.49
Purity≥95%
Storage-20°C

Computed Descriptor

IUPAC Nameethyl (9Z,11E,13E)-octadeca-9,11,13-trienoate
InChIInChI=1S/C20H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h7-12H,3-6,13-19H2,1-2H3/b8-7+,10-9+,12-11-
InChIKeyYVGCHYVFHLTZIM-CPIUXLSQSA-N
SMILESCCCCC=CC=CC=CCCCCCCCC(=O)OCC