Α-Eleostearic_acid
α-Eleostearic acid
Chemical compound
α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated fatty acid and one of the 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). Its high degree of unsaturation gives tung oil its properties as a drying oil.
| Names | |
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| Preferred IUPAC name
(9Z,11E,13E)-Octadeca-9,11,13-trienoic acid | |
| Identifiers | |
3D model (JSmol) |
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| 1726551 | |
| ChEBI | |
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| ECHA InfoCard | 100.007.300  |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H30O2 | |
| Molar mass | 278.43 g/mol |
| Melting point | 48 °C (118 °F; 321 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
α-Eleostearic acid is found in the oils extracted from seeds. Tung oil has 82% α-eleostearic acid. Bitter gourd seed oil has 60% α-eleostearic acid.
Eleo- is a prefix derived from the Greek word for olive, ἔλαιον.[6]
- 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. doi:10.1016/S0021-9258(18)76213-3. Archived from the original (PDF) on 2007-02-21. 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. doi:10.1093/jn/136.8.2153. PMID 16857834.
- Kobori M, Ohnishi-Kameyama M, Akimoto Y, Yukizaki C, Yoshida M (2008). "α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd". Journal of Agricultural and Food Chemistry. 56 (22): 10515–10520. doi:10.1021/jf8020877. PMID 18959405.
- Kohno H, Yasui Y, Suzuki R, Hosokawa M, Miyashita K, Tanaka T (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. 110 (6): 896–901. doi:10.1002/ijc.20179. PMID 15170673. S2CID 1817375.
- Senning A (2006-10-30). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. ISBN 978-0-08-048881-3.