9(Z),11(E),13(E)-Octadecatrienoic Acid
Item № 10008349
CAS № 506-23-0
Purity ≥95%
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1 mg $45.00 $0.00
5 mg $203.00 $0.00
10 mg $360.00 $0.00

Pricing updated 2015-09-04. Prices are subject to change without notice.

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Description
Synonyms
  • α-ESA
  • α-Eleostearic Acid

9(Z),11(E),13(E)-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.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

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Technical Information
Formal Name 9Z,​11E,​13E-​octadecatrienoic acid
CAS Number 506-23-0
Synonyms
  • α-ESA
  • α-Eleostearic Acid
Molecular Formula C18H30O2
Formula Weight 278.4
Purity ≥95%
Formulation A solution in methanol
λmax 270 nm
SMILES CCCC/C=C/C=C/C=C\CCCCCCCC(O)​=O
InChI Code ​1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)​20/h5-10H,2-4,11-17H2,1H3,(H,19,20)​/b6-5+,8-7+,10-9-
InChI Key CUXYLFPMQMFGPL-WPOADVJFSA-N

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -80°C
Shipping Wet ice in continental US; may vary elsewhere
Stability 1 year
Product Downloads & Resources
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Download Product Insert 96 Kb PDF

Download Safety Data Sheet (SDS) 33 Kb PDF

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Additional Information

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Inserts
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References & Background Reading
Product Description 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).

Background Reading

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).

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).

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).

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