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Ricinoleic acid

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Ricinoleic acid
Ricinoleic acid.svg
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
ECHA InfoCard 100.004.974
KEGG
PubChem CID
UNII
  • 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 checkY
    Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N checkY
  • 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
  • O=C(O)CCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
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).
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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 castor plant (Ricinus communis L., Euphorbiaceae) seeds and is also found in the sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.

Production

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.

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

Use

Sebacic acid ((CH2)8(CO2H)2), which is used in preparing certain nylons, is produced by cleavage of ricinoleic acid. The coproduct is 2-octanol. The mechanism of the base-induced cleavage is proposed to proceed by initial dehydrogenation of the secondary alcohol, affording the ketone. The resulting α,β-unsaturated ketone undergoes retroaldol reaction, resulting in lysis of the C-C bond.

The zinc salt is used in personal care products such as deodorants.

See also


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