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Fatty acids
Punicic acid
Другие языки:

Punicic acid

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Punicic acid
Punicic acid
Names
Preferred IUPAC name
(9Z,11E,13Z)-Octadeca-9,11,13-trienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
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- ☒N
    Key: CUXYLFPMQMFGPL-BGDVVUGTSA-N ☒N
  • 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-
    Key: CUXYLFPMQMFGPL-BGDVVUGTBE
  • CCCC\C=C/C=C/C=C\CCCCCCCC(=O)O
Properties
C18H30O2
Molar mass 278.43 g/mol
Melting point 44 to 45 °C (111 to 113 °F; 317 to 318 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid, 18:3 cis-9, trans-11, cis-13. It is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil. It has also been found in the seed oils of snake gourd.

Punicic acid is a conjugated linolenic acid or CLnA; i.e. it has three conjugated double bonds. It is chemically similar to the conjugated linoleic acids, or CLA, which have two. It has also been classified as an "n-5" or "omega-5" polyunsaturated fatty acid. In lab rats, punicic acid was converted to the CLA rumenic acid (9Z11E-CLA).In vitro, it shows anti-invasive activity against prostate cancer cells. OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.

Punicic acid makes up around 65% of the fatty acids in pomegranate seed oil.

See also


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