9Z,11E,13E-Octadecatrienoic Acid ethyl esterA conjugated polyunsaturated fatty acid

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

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Synonym: α-ESA ethyl ester; Ethyl α-eleostearate
Application: A conjugated polyunsaturated fatty acid
CAS Number: 42021-86-3
Molecular Weight: 306.5
Molecular Formula: C20H34O2
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* Refer to Certificate of Analysis for lot specific data (including water content).
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A conjugated polyunsaturated fatty acid commonly found in plant seed oil which accounts for about 70% in tung oil and 60% of the total fatty acid composition of bitter gourd seed 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.


References

1 Yasui, Y., Hosokawa, M., Sahara, T., et al. Bitter gourd seed fatty acid rich in 9c,11t,13t-conjugated linolenic acid induces apoptosis and up-regulates the GADD45, p53 and PPARγ in human colon cancer caco-2 cells. Prostaglandins Leukot Essent Fatty Acids 75 113-119 (2005). 2 Tsuzuki, T., Tokuyama, Y., Igarashi, M., et al. Tumor growth suppression by a α-eleostearic acid, linolenic acid isomer with a conjugated triene system, via lipid peroxidation. Carcinogenesis 25(8) 1417-1425 (2004). 3 Mizushina, Y., Tsuzuki, T., Eitsuka, T., et al. Inhibitory action of conjugated C18-fatty acids on DNA polymerases and DNA topoisomerases. Lipids 39(10) 977-983 (2004).

Formulation :
A solution in ethanol
Physical State :
Liquid
Solubility :
Soluble in DMSO (~30 mg/ml), DMF (~30 mg/ml), and ethanol. Insoluble in water.
Storage :
Store at -20° C
Boiling Point :
78° C
IC50 :
Apoptosis was induced via lipid peroxidation: EC5050 = 20 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
MDL Number :
MFCD12912283
SMILES :
CCCC/C=C/C=C/C=C\\CCCCCCCC(=O)OCC

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Certificate of Analysis

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