8211. Ricinoleic Acid

Nomenclature

CAS number: 141-22-0
(9Z,12R)-12-Hydroxy-9-octadecenoic acid; d-12-hydroxyoleic acid.
C18H34O3; mol wt 298.46.
C 72.44%, H 11.48%, O 16.08%.

Description and references

Found primarily in oils from the seeds of Ricinus spp, Euphorbiaceae. Accounts for about 90% of the triglyceride fatty acids of castor oil, and up to about 40% of the glyceride fatty acids of ergot oil. Bibliography on its isoln: Ralston, Fatty Acids (New York, 1948) p 189. Also isolated from Linum mucronatum (flax), Linaceae: Kleiman, Spencer, Lipids 6, 962 (1971). Structure: Goldsobel, Ber. 27, 3121 (1894). Mechanism of biosynthesis: Morris, Biochem. Biophys. Res. Commun. 29, 311 (1967).

Chemical structure

Properties

Liquid. d427.4 0.940; mp 5.5°; bp10 245°. [α]D22 +6.67°; [α]D26 +7.15° (c = 5 in acetone). nD20 1.4716. Neutralization value 187.98; iodine value 85.05. Sol in alcohol, acetone, ether, chloroform (cf. the solubilities of castor oil).

Derivative

Acid sulfate.

Nomenclature

CAS number: 36634-48-7
Ricinolsulfuric acid.
C18H34O6S; mol wt 378.52.
C 57.12%, H 9.05%, O 25.36%, S 8.47%.

Properties

Obtained by the action of chlorosulfonic acid. Viscous brown liquid with weak blue fluorescence. Sol in water (about 10%), alcohol, ether, chloroform.

Derivative

Sodium salt.

Nomenclature

CAS number: 5323-95-5
Sodium ricinoleate; Soricin; Colidosan.
C18H33NaO3; mol wt 320.44.
C 67.47%, H 10.38%, Na 7.17%, O 14.98%.

Properties

Sodium salts of the fatty acids from castor oil. White or slightly yellow, odorless or almost odorless powder. Sol in water or alcohol. The aq soln is alkaline.

Use

In textile finishing; sometimes added to Turkey red oil, dry-cleaning soaps.

Therapeutic Category

Has been used in contraceptive jellies. The sodium salt has been used as sclerosing agent.

Keywords

Sodium Ricinoleate: Sclerosing Agent