Sebacic acid is a naturally occurring dicarboxylic acid with the formula (CH2)8(CO2H)2. 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.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||202.250 g·mol−1|
|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|
|Acidity (pKa)||4.720, 5.450|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Potential medical significanceEdit
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 of which sebacic acid is a major component. 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-octadecaenoic acid (5-oxo-ODE). 5-Oxo-ODE is 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.
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