Alpha-Parinaric acid

α-Parinaric acid

Names
IUPAC name (9Z,11E,13E,15Z)-octadeca-9,11,13,15-tetraenoic acid
Other names cis-parinaric acid α-parinaric acid
Identifiers
CAS Number	18427-44-6 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:32409 Y
ChemSpider	4574382 Y
PubChem CID	5460995
InChI InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-10H,2,11-17H2,1H3,(H,19,20)/b4-3-,6-5+,8-7+,10-9- Y Key: IJTNSXPMYKJZPR-ZSCYQOFPSA-N Y InChI=1/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-10H,2,11-17H2,1H3,(H,19,20)/b4-3-,6-5+,8-7+,10-9- Key: IJTNSXPMYKJZPR-ZSCYQOFPBE
SMILES O=C(O)CCCCCCC/C=C\C=C\C=C\C=C/CC
Properties
Chemical formula	C18H28O2
Molar mass	276.41372
Melting point	85 to 86 °C (185 to 187 °F; 358 to 359 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

α-Parinaric acid is a conjugated polyunsaturated fatty acid. Discovered by Tsujimoto and Koyanagi in 1933, it contains 18 carbon atoms and 4 conjugated double bonds. The repeating single bond-double bond structure of α-parinaric acid distinguishes it structurally and chemically from the usual "methylene-interrupted" arrangement of polyunsaturated fatty acids that have double-bonds and single bonds separated by a methylene unit (−CH₂−). Because of the fluorescent properties conferred by the alternating double bonds, α-parinaric acid is commonly used as a molecular probe in the study of biomembranes.

α-Parinaric acid occurs naturally in the seeds of the makita tree (Parinari laurina), a tree found in Fiji and other Pacific islands. Makita seeds contain about 46% α-parinaric acid, 34% α-eleostearic acid as major components, with lesser amounts of saturated fatty acids, oleic acid and linoleic acid. α-Parinaric acid is also found in the seed oil of Impatiens balsamina, a member of the family Balsaminaceae. The major fatty acids of Impatiens balsamina are 4.7% palmitic acid, 5.8% stearic acid, 2.8% arachidic acid, 18.3% oleic acid, 9.2% linoleic acid, 30.1% linolenic acid and 29.1% α-parinaric acid. It is also present in the fungus Clavulina cristata, and the plant Sebastiana brasiliensis (family Euphorbiaceae).