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Fatty acids
15,16-Dihydroxy-alpha-eleostearic acid
Другие языки:

    15,16-Dihydroxy-alpha-eleostearic acid

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    15,16-Dihydroxy-α-eleostearic acid
    15,16-Dihydroxy-alpha-eleostearic acid.svg
    Names
    Preferred IUPAC name
    (9Z,11E,13E)-15,16-Dihydroxyoctadeca-9,11,13-trienoic acid
    Identifiers
    3D model (JSmol)
    ChemSpider
    PubChem CID
    • InChI=1S/C18H30O4/c1-2-16(19)17(20)14-12-10-8-6-4-3-5-7-9-11-13-15-18(21)22/h4,6,8,10,12,14,16-17,19-20H,2-3,5,7,9,11,13,15H2,1H3,(H,21,22)/b6-4-,10-8+,14-12+
      Key: OBMDTPZEEDLBKM-ZMLXCLEUSA-N
    • OC(CCCCCCC/C=C\C=C\C=C\C(O)C(O)CC)=O
    Properties
    C18H30O4
    Molar mass 310.434 g·mol−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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    15,16-Dihydroxy-α-eleostearic acid, or 15,16-Dihydroxy-(9Z,11E,13E)-9,11,13-octadecatrienoic acid, is an organic compound with formula C
    18    H
    30    O
    4    , or H3C-CH2-(-CH(OH)-)2(-CH=CH-)3-(-CH2-)7-(C=O)OH. It can be seen as derived from α-eleostearic acid by the replacement of two hydrogen atoms by two hydroxyl (OH) groups.

    The compound is found in the pulp and seeds of bitter melons (the fruits of Momordica charantia). It has been found to induce apoptosis in HL60 leukemia cells in vitro at a concentration of 160 μM, although it is less potent in this regard than the unsubstituted α-eleostearic acid (also found in the seed oil). While α-eleostearic acid has been found to prevent carcinogenesis in rats, this derivative does not seem to have that effect.

    The compound can be extracted from the fruit with ethanol, and is soluble in ethyl acetate but not in water or acetone.

    See also


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