Punicic acid

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Punicic acid
Punicic acid
Names
IUPAC name
9Z,11E,13Z-octadeca-9,11,13-trienoic acid
Identifiers
544-72-9 YesY
ChEBI CHEBI:8638 N
ChemSpider 4444570 N
Jmol 3D model Interactive image
PubChem 5281126
  • 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).
N verify (what is YesYN ?)
Infobox references

Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid, 18:3 (n-5). It is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil. It is also found in the seed oils of snake gourd.[1]

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. In lab rats, it was found that punicic acid was converted to the CLA rumenic acid (9Z11E-CLA).[2] In vitro, it shows anticancer activity against prostate cancer cells.[3] OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.[4]

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

See also

References

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