Name: 9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester
Rating: 5 (10 reviews)

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HIT ID:HIT214321361
Cas No:42021-86-3
常用名:9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester
常用名:9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester
IUPAC:ethyl (9Z,11E,13E)-octadeca-9,11,13-trienoate
IUPAC:ethyl (9Z,11E,13E)-octadeca-9,11,13-trienoate
InChI key:YVGCHYVFHLTZIM-CPIUXLSQSA-N

分子式:C20H34O2
分子量:306.49
氢键供体数 (HBD):
氢键受体数 (HBA):
LogP:
SMILES:CCCC\C=C\C=C\C=C/CCCCCCCC(=O)OCC
SMILES:CCCC\C=C\C=C\C=C/CCCCCCCC(=O)OCC

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.

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