9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester

Cayman Chemical Item Number 10008350

α-ESA ethyl ester; Ethyl α-eleostearate (CAS 42021-86-3)

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Description

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.1 α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats.2 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.1 In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 µM.2 It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 µM for different isoforms of the enzymes.3 α-ESA ethyl ester is a neutral, more lipid soluble form of the free acid.

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).

Synonyms
  • α-ESA ethyl ester
  • Ethyl α-eleostearate
Formal Name 9Z,​11E,​13E-​octadecatrienoic acid,​ ethyl ester
CAS Number 42021-86-3
Molecular Formula C20H34O2
Formula Weight 306.5
Formulation A solution in ethanol
Purity ≥98%
λmax 261, 270, 281 nm
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CCCC/C=C/C=C/C=C\CCCCCCCC(OCC)​=O
InCHI Code
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​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-
InCHI Key
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YVGCHYVFHLTZIM-CPIUXLSQSA-N

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Size Price Quantity Subtotal
1 mg $45.00 $0.00
5 mg $203.00 $0.00
10 mg $360.00 $0.00
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9(Z),11(E),13(E)-Octadecatrienoic Acid methyl ester

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