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
ChEBI	CHEBI:28592
ChemSpider	558800
Jmol interactive 3D	Image
PubChem	643684
UNII	I2D0F69854
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 Key: WBHHMMIMDMUBKC-QJWNTBNXSA-N 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/cm^3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid^[1] 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.

Production

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.^[2] The zinc salt is used in personal care products,^[3] such as deodorants.^[4]

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.^[5]

Biological activities

Ricinoleic acid exerts analgesic and anti-inflammatory effects.^[6]

Ricinoleic acid specifically activates the EP3 prostanoid receptor for prostaglandin E2.^[7]

Ricinoleic acid acts as a specific algicide for the control of blue-green algae.^[8]

See also

• Castor oil
• Ricinelaidic acid, the trans isomer of ricinoleic acid
• Ricinolein, the triglyceride of ricinoleic acid
• Sodium ricinoleate, the sodium salt of ricinoleic acid
• Polyglycerol polyricinoleate, a polymer of glycerol with ricinoleic acid side chains, used as an emulsifier in chocolate
• Undecylenic acid, a product of pyrolysis of ricinoleic acid
• Lesquerolic acid, a similar chemical, which could be described as ricinoleic acid with -CH₂-CH₂- group inserted between carboxyl group and the double bound.

References

1. Frank D. Gunstone, John L. Harwood, Albert J. Dijkstra (2007). The Lipid Handbook. 10: CRC Press. p. 1472. ISBN 1420009672.
2. James AT, Hadaway HC, Webb JP (May 1965). "The biosynthesis of ricinoleic acid". Biochem. J. 95: 448–52. PMC 1214342. PMID 14340094.
3. "zinc ricinoleate". Environmental Working Group.
4. Tom's of Maine - About Our Products
5. Rider, T.H. (November 1931). "The purification of sodium ricinoleate ". Journal of the American Chemical Society 53: 4130–4133. doi:10.1021/ja01362a031. Retrieved 5 February 2013.
6. Vieira C, Evangelista S, Cirillo R, Lippi A, Maggi CA, Manzini S (2000). "Effect of ricinoleic acid in acute and subchronic experimental models of inflammation". Mediators Inflamm. 9 (5): 223–8. doi:10.1080/09629350020025737. PMC 1781768. PMID 11200362.
7. Tunaru S, Althoff TF, Nüsing RM, Diener M, Offermanns S (2012). "Castor oil induces laxation and uterus contraction via ricinoleic acid activating prostaglandin EP3 receptors". Proc Natl Acad Sci USA 109 (23): 9179–9184. doi:10.1073/pnas.1201627109. PMC 3384204. PMID 22615395.
8. US 4398937, "Selective algaecides for control of cyanochloronta", published 1983