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| Names | |
|---|---|
| Preferred IUPAC name Decanedioic acid | |
| Other names 1,8-Octanedicarboxylic acid Decane-1,10-dioic acid | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.003.496 |
| EC Number |
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| MeSH | C011107 |
| UNII | |
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| Properties | |
| C10H18O4 | |
| Molar mass | 202.250 g·mol−1 |
| Density | 1.209 g/cm3 |
| Melting point | 131 to 134.5 °C (267.8 to 274.1 °F; 404.1 to 407.6 K) |
| Boiling point | 294.4 °C (561.9 °F; 567.5 K) at 100 mmHg |
| 0.25 g/L[1] | |
| Acidity (pKa) | 4.720, 5.450[1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Sebacic acid is a naturally occurringdicarboxylic acid with the chemical formulaHO2C(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 ofcastor oil.[2]
In the industrial setting, sebacic acid and its homologues such asazelaic acid can be used as a monomer fornylon 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.
Sebacic acid is produced fromcastor oil by cleavage ofricinoleic acid, which is obtained from castor oil.Octanol andglycerin are byproducts.[2]
It can also be obtained fromdecalin via the ahydroperoxide, which rearranges to give a hydroxycyclodecanone, which dehydrates to give cyclodecenone, a precursor to sebacic acid.[3]
Sebacic acid has also been produced commercially byKolbe electrolysis ofadipic acid.[4]
Sebum is a secretion by skinsebaceous glands. It is awaxy set oflipids composed oftriglycerides (≈41%),wax esters (≈26%),squalene (≈12%), andfree fatty acids (≈16%).[6][7] Included in the free fatty acid secretions in sebum arepolyunsaturated 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, astructural analog of5-oxo-eicosatetraenoic acid and like this oxo-eicosatetraenoic acid is an exceptionally potent activator ofeosinophils,monocytes, and other pro-inflammatory cells from humans and other species. This action is mediated by theOXER1 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.[8]
| Authority control databases: National |
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