 | |
| Names | |
|---|---|
| Preferred IUPAC name (9Z,12R)-12-Hydroxyoctadec-9-enoic acid | |
| Other names (R)-12-Hydroxy-9-cis-octadecenoic acid | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.004.974 |
| KEGG |
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| UNII | |
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| Properties | |
| C18H34O3 | |
| Molar mass | 298.461 g/mol |
| Appearance | Yellow viscous liquid |
| Density | 0.945 g/cm3 |
| Melting point | 5 °C (41 °F; 278 K) |
| Boiling point | 245 °C (473 °F; 518 K) |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 228 °C (442 °F; 501 K) |
| Safety data sheet (SDS) | Fisher Scientific |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is afatty acid. It is anunsaturatedomega-9 fatty acid[1] and ahydroxy acid. It is a major component of the seed oil obtained from the seeds ofcastor plant (Ricinus communis L.,Euphorbiaceae), the plant that producesricin. It is also found in thesclerotium ofergot (Claviceps purpurea Tul.,Clavicipitaceae). About 90% of the fatty acid content incastor oil is thericinolein.
Ricinoleic acid is manufactured for industries bysaponification orfractional distillation ofhydrolyzed castor oil.[2]
The first attempts to prepare ricinoleic acid were made byFriedrich Krafft in 1888.[3]
Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certainnylons, is produced by cleavage of ricinoleic acid. The coproduct is2-octanol.[4][5] The mechanism of the base-induced cleavage is proposed to proceed by initial dehydrogenation of the secondary alcohol, affording the ketone. The resultingα,β-unsaturated ketone undergoesretroaldol reaction, resulting in lysis of the C-C bond.[6]
Thezinc salt is used in personal care products such asdeodorants.[7]
