Α-Eleostearic acid
18-Carbon polyunsaturated fatty acid
From Wikipedia, the free encyclopedia
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.
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| 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 | |
| ChemSpider | |
| 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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Biochemical properties
In their pioneering work on essential fatty acids, George Burr, Mildred Burr and Elmer Miller compared the nutritional properties of α-eleostearic acid (ESA) to that of its isomer alpha-linolenic acid (ALA). ALA relieved essential fatty acid deficiency; ESA 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]
Sources
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.
Etymology
Eleo- is a prefix derived from the Greek word for olive, ἔλαιον.[6]