Ricinoleic acid

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Ricinoleic acid
Ricinoleic acid.svg
IUPAC name
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid
Other names
(R)-12-Hydroxy-9-cis-octadecenoic acid
3D model (JSmol)
ECHA InfoCard 100.004.974
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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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.


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 such as deodorants.[3]

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.[4]

Biological activities[edit]

Ricinoleic acid exerts analgesic and anti-inflammatory effects.[5]

Ricinoleic acid specifically activates the EP3 prostanoid receptor for prostaglandin E2.[6]

Ricinoleic acid acts as a specific algicide for the control of cyanobacteria (formerly called blue-green algae).[7]

See also[edit]


  1. ^ Frank D. Gunstone; John L. Harwood; Albert J. Dijkstra (2007). The Lipid Handbook. 10: CRC Press. p. 1472. ISBN 978-1420009675.CS1 maint: location (link)
  2. ^ James AT, Hadaway HC, Webb JP (May 1965). "The biosynthesis of ricinoleic acid". Biochem. J. 95: 448–52. PMC 1214342. PMID 14340094.
  3. ^ Tom's of Maine - About Our Products
  4. ^ Rider, T.H. (November 1931). "The purification of sodium ricinoleate ". Journal of the American Chemical Society. 53 (11): 4130–4133. doi:10.1021/ja01362a031.
  5. ^ 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.
  6. ^ 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.
  7. ^ US 4398937, "Selective algaecides for control of cyanochloronta", published 1983