Ricinoleic acid

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Ricinoleic acid
Ricinoleic acid.svg
Identifiers
CAS number 141-22-0 YesY
PubChem 643684
ChemSpider 558800 YesY
UNII I2D0F69854 YesY
ChEBI CHEBI:28592 YesY
Jmol-3D images Image 1
Properties
Molecular formula C18H34O3
Molar mass 298.461 g/mol
Except where noted otherwise, 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] 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.[2]

Production[edit]

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.[3] The zinc salt is used in personal care products,[4] such as deodorants.[5]

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.[6]

Biological activities[edit]

Ricinoleic acid exerts analgesic and anti-inflammatory effects.[7]

Ricinoleic acid specifically activates the EP3 prostanoid receptor for prostaglandin E2.[8]

Ricinoleic acid acts as a specific algicide for the control of blue-green algae.[9]

See also[edit]

References[edit]

  1. ^ Frank D. Gunstone, John L. Harwood, Albert J. Dijkstra (2007). The Lipid Handbook. 10: CRC Press. p. 1472. ISBN 1420009672. 
  2. ^ "Castor Oil Uses". Retrieved 23 July 2014. 
  3. ^ James AT, Hadaway HC, Webb JP (May 1965). "The biosynthesis of ricinoleic acid". Biochem. J. 95: 448–52. PMC 1214342. PMID 14340094. 
  4. ^ "zinc ricinoleate". Environmental Working Group. 
  5. ^ Tom's of Maine - About Our Products
  6. ^ 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. 
  7. ^ 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. 
  8. ^ 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. 
  9. ^ US 4398937, "Selective algaecides for control of cyanochloronta", published 1983