Sebacic acid
Chemical compound
Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil.
In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used as a monomer for nylon 610, plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc.
It can be used as a surfactant in the lubricating oil industry to increase the antirust properties of lubricating oils on metals.
01Production and reactions
Sebacic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. Octanol and glycerin are byproducts.
It can also be obtained from decalin via a hydroperoxide, which rearranges to give a hydroxycyclodecanone, which dehydrates to give cyclodecenone, a precursor to sebacic acid.
Sebacic acid has also been produced commercially by Kolbe electrolysis of adipic acid.
1,10-Decanediol is synthesized by reduction of diethyl sebacate, e.g. with sodium/ethanol.
02Potential medical significance
Sebum is a secretion by skin sebaceous glands. It is a waxy set of lipids composed of triglycerides (≈41%), wax esters (≈26%), squalene (≈12%), and free fatty acids (≈16%). Included in the free fatty acid secretions in sebum are polyunsaturated fatty acids and sebacic acid. Sebacic acid is also found in other lipids that coat the skin surface. Human neutrophils can convert sebacic acid to its 5-oxo analog, i.e., 5-oxo-6E,8Z-octadecenoic acid, a structural analog of 5-oxo-eicosatetraenoic acid and like this oxo-eicosatetraenoic acid is an exceptionally potent activator of eosinophils, monocytes, and other pro-inflammatory cells from humans and other species. This action is mediated by the OXER1 receptor on these cells. It is suggested that sebacic acid is converted to its 5-oxo analog during, and thereby stimulates pro-inflammatory cells to contribute to the worsening of, various inflammatory skin conditions.
Sources and credits
This article is adapted from the Wikipedia article “Sebacic acid”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Sebacic acid 3D ball.png by Jynto (talk), CC0
- Me2sabacateTocycloC10diol.svg by Smokefoot, CC BY 4.0
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