7189. Petroselinic Acid

Nomenclature

CAS number: 593-39-5
(6Z)-6-Octadecenoic acid; cis-6-Octadecenoic acid; petroselic acid; cis-5-heptadecylene-1-carboxylic acid; cis6-octadecylenic acid.
C18H34O2; mol wt 282.46.
C 76.54%, H 12.13%, O 11.33%.

Description and references

Isoln from parsley seed oil, the oil extracted from dried ripe seed of Petroselinum hortense Hoffm., Umbelliferae: Fore et al., J. Am. Oil Chem. Soc. 37, 490 (1960).

Chemical structure

Properties

Leaflets from petr ether, mp 29.5-30.1°. bp18 237-238°; d440 0.8700. nD40 1.4533. Low temp solubilities: Heptane at -10° = 0.50 g/100 g solution; methanol at -20° = 0.48 g/100 g; ethyl acetate at -20° = 0.73 g/100 g; ether at -20° = 3.52 g/100 g. Ozonolysis yields 85% of adipic acid. Neutralization equivalent: 282.45; iodine value 89.87%.

Derivative

Methyl ester.

Nomenclature

CAS number: 2777-58-4
C19H36O2; mol wt 296.49.
C 76.97%, H 12.24%, O 10.79%.

Properties

Liq, d420 0.8767; nD20 1.4501; bp10 208-210°.

Derivative

Glyceryl triester.

Nomenclature

CAS number: 3296-43-3
Glyceryl tripetroselinate; tripetroselin.
C57H104O6; mol wt 885.43.
C 77.32%, H 11.84%, O 10.84%.

Properties

Solidifies at 16.5°. nD40 1.4619.

Derivative

Amide.

Nomenclature

CAS number: 24222-02-4
Petroselinamide.
C18H35NO; mol wt 281.48.
C 76.81%, H 12.53%, N 4.98%, O 5.68%.

Properties

Needles, mp 76°.