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Fatty acids
Alpha-Eleostearic acid
Другие языки:

Alpha-Eleostearic acid

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α-Eleostearic acid
α-Eleostearic acid
Names
Preferred IUPAC name
(9Z,11E,13E)-Octadeca-9,11,13-trienoic acid
Identifiers
3D model (JSmol)
1726551
ChEBI
ChemSpider
ECHA InfoCard 100.007.300
EC Number
  • 208-029-2
KEGG
PubChem CID
UNII
  • 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- checkY
    Key: CUXYLFPMQMFGPL-WPOADVJFSA-N checkY
  • 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-
  • O=C(O)CCCCCCC/C=C\C=C\C=C\CCCC
Properties
C18H30O2
Molar mass 278.43 g/mol
Melting point 48 °C (118 °F; 321 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

Biochemical properties

α-Eleostearic acid makes up about 60% of the fatty acids from bitter gourd oil.

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.

In rats, α-eleostearic acid is converted to a conjugated linoleic acid. The compound has been found to induce programmed cell death of fat cells, and of HL60 leukemia cells in vitro at a concentration of 20 μM. Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent azoxymethane-induced colon carcinogenesis in rats.

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.

See also


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