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 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.

Ricinoleic acid
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
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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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][5] 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.[6]

The zinc salt is used in personal care products such as deodorants.[7]

See also

References
  1. Frank D. Gunstone; John L. Harwood; Albert J. Dijkstra (2007). The Lipid Handbook. CRC Press. p. 1472. ISBN 978-1420009675.
  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. Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61. doi:10.15227/orgsyn.001.0061.
  6. Diamond, M. J.; Binder, R. G.; Applewhite, T. H. (1965). "Alkaline cleavage of hydroxy unsaturated fatty acids. I. Ricinoleic acid and lesquerolic acid". Journal of the American Oil Chemists' Society. 42 (10): 882–884. doi:10.1007/BF02541184. S2CID 85036911.
  7. Tom's of Maine - About Our Products
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