Ricinoleic acid

Ricinoleic acid

Names
IUPAC name (9Z,12R)-12-Hydroxyoctadec-9-enoic acid
Other names R12-Hydroxy-9-cis-octadecenoic acid
Identifiers
CAS Number	141-22-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28592 Y
ChemSpider	558800 Y
ECHA InfoCard	100.004.974
KEGG	C08365 N
PubChem	643684
UNII	I2D0F69854 Y
InChI InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1 Y Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N Y InChI=1/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1 Key: WBHHMMIMDMUBKC-QJWNTBNXBT
SMILES O=C(O)CCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
Chemical formula	C18H34O3
Molar mass	298.461 g/mol
Density	0.945 g/cm3
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

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil. The zinc salt is used in personal care products, such as deodorants.

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.

Ricinoleic acid exerts analgesic and anti-inflammatory effects.

Ricinoleic acid specifically activates the EP3 prostanoid receptor for prostaglandin E2.

Ricinoleic acid acts as a specific algicide for the control of blue-green algae.