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 the seeds of castor plant (Ricinus communis L., Euphorbiaceae), the plant that produces ricin. It is also found in the sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the ricinolein.
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| Names | |
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| Preferred IUPAC name
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid | |
| Other names
(R)-12-Hydroxy-9-cis-octadecenoic acid
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.004.974 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C18H34O3 | |
| Molar mass | 298.461 g/mol |
| Appearance | Yellow viscous liquid |
| Density | 0.945 g/cm3 |
| Melting point | 5 °C (41 °F; 278 K) |
| Boiling point | 245 °C (473 °F; 518 K) |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Flash point | 228 °C (442 °F; 501 K) |
| Safety data sheet (SDS) | Fisher Scientific |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
editRicinoleic 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
editSebacic 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
edit- 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 bond.
- 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
edit- ^ Frank D. Gunstone; John L. Harwood; Albert J. Dijkstra (2007). The Lipid Handbook. CRC Press. p. 1472. ISBN 978-1-4200-0967-5.
- ^ 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.
- ^ Rider, T. H. (November 1931). "The Purification of Sodium Ricinoleate". Journal of the American Chemical Society. 53 (11): 4130–4133. doi:10.1021/ja01362a031.
- ^ Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523. ISBN 3-527-30673-0.
- ^ Roger Adams, C. S. Marvel (1921). "Methyl-n-hexylcarbinol". Organic Syntheses. 1: 61. doi:10.15227/orgsyn.001.0061.
- ^ 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.
- ^ Tom's of Maine – About Our Products