alpha-Eleostearic acid
| α-Eleostearic acid |
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(9Z,11E,13E)-Octadeca-9,11,13-trienoic acid
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| Identifiers |
| CAS number |
506-23-0 |
| ChemSpider |
4444560 Y |
| ChEBI |
CHEBI:10275 Y |
| Jmol-3D images |
Image 1 |
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O=C(O)CCCCCCC/C=C\C=C\C=C\CCCC
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InChI=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- Y
Key: CUXYLFPMQMFGPL-WPOADVJFSA-N Y
InChI=1/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-
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| Properties |
| Molecular formula |
C18H30O2 |
| Molar mass |
278.43 g/mol |
| Melting point |
48 °C[1]
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Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
| Infobox references |
α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated linolenic acid and one of the conformational isomers of octadecatrienoic acid. It is often called simply eleostearic acid although there is also a β-eleostearic acid (the all-trans or (9E,11E,13E) isomer)
The acid makes up approximately 80% of the fatty acids in tung oil and 60% of bitter gourd seed oil. Its high degree of unsaturation gives tung oil its properties as a drying oil.
Biochemical properties
In their pioneering work on essential fatty acids, Burr, Burr and Miller compared the nutritional properties of α-eleostearic acid (ELA) to that of its isomer alpha-linolenic acid (ALA). ALA relieved essential fatty acid deficiency; ELA did not.[1]
In rats, α-eleostearic acid is converted to a conjugated linoleic acid.[2]The compound has been found to induce programmed cell death of fat cells,[3] and of HL60 leukemia cells in vitro at a concentration of 20 μM.[4] Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent azoxymethane-induced colon carcinogenesis in rats.[5]
See also
References
- ^ a b Burr, G.O.; Burr, M.M.; Miller, E. (1932). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol. Chem. 97 (1): 1–9. http://www.jbc.org/cgi/reprint/97/1/1.pdf. Retrieved 2007-01-17.
- ^ Tsuzuki T, Kawakami Y, Abe R, et al. (1 August 2006). "Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid". J Nutr 136 (8): 2153–9.. PMID 16857834. http://jn.nutrition.org/cgi/content/abstract/136/8/2153. Retrieved 2007-01-17.
- ^ Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K (2002). "Regulation of apoptosis through arachidonate cascade in mammalian cells". Appl Biochem Biotechnol 102-103 (1-6): 239–50. doi:10.1385/ABAB:102-103:1-6:239. PMID 12396127.
- ^ Masuko Kobori, Mayumi Ohnishi-Kameyama, Yukari Akimoto, Chizuko Yukizaki and Mitsuru Yoshida (2008) α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd. Journal of Agricultural and Food Chemistry, volume 56, issue 22, pages 10515–10520. doi:10.1021/jf8020877
- ^ H. Kohno, Y. Yasui, R. Suzuki, M. Hosokawa, K. Miyashita, T. Tanaka (2004), Dietary seed oil rich in conjugated linolenic acid from bitter melon inhibits azoxymethane-induced rat colon carcinogenesis through elevation of colonic PPAR γ expression and alteration of lipid composition. International Journal of Cancer, volume 110, pages 896–901.