Ricinoleic acid

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

Names
IUPAC name (9Z,12R)-12-Hydroxyoctadec-9-enoic acid
Other names (R)-12-Hydroxy-9-cis-octadecenoic acid
Identifiers
CAS Number	141-22-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28592
ChemSpider	558800
ECHA InfoCard	100.004.974
KEGG	C08365
PubChem CID	643684
UNII	I2D0F69854
CompTox Dashboard (EPA)	DTXSID0041567
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

Production

Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil.[2]

The first attempts to prepare ricinoleic acid were made by Friedrich Krafft in 1888.[3]

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.[4]

The zinc salt is used in personal care products such as deodorants.[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 cyanobacteria (formerly called blue-green algae).[8]

See also

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

References

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 (2): 448–52. doi:10.1042/bj0950448. PMC 1214342. PMID 14340094.
3. Rider, T. H. (November 1931). "The Purification of Sodium Ricinoleate". Journal of the American Chemical Society. 53 (11): 4130–4133. doi:10.1021/ja01362a031.
4. Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.
5. Tom's of Maine - About Our Products
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. Bibcode:2012PNAS..109.9179T. doi:10.1073/pnas.1201627109. PMC 3384204. PMID 22615395.
8. US 4398937, "Selective algaecides for control of cyanochloronta", published 1983