Sebacic acid
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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)
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| MeSH | C011107 |
PubChem CID
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula Page Module:Chem2/styles.css has no content.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.[2]
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.
Production 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.[2]
It can also be obtained from decalin via the a hydroperoxide, which rearranges to give a hydroxycyclodecanone, which dehydrates to give cyclodecenone, a precursor to sebacic acid.[3]
Sebacic acid has also been produced commercially by Kolbe electrolysis of adipic acid.[4]
1,10-Decanediol is synthesized by reduction of diethyl sebacate, e.g. with sodium/ethanol.[6]
Potential 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%).[7][8] 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., Template:Chem name, 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.[9]
References
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- ^ a b Page Module:Citation/CS1/styles.css has no content.Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 °C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.
- ^ a b Script error: No such module "Template wrapper".
- ^ Script error: No such module "Template wrapper".
- ^ Page Module:Citation/CS1/styles.css has no content.Seko, Maomi; Yomiyama, Akira; Isoya, Toshiro (1979). "Development of Kolbe Electrosynthesis of Sebacic Acid". CEER, Chemical Economy & Engineering Review. 11 (9): 48-50.
- ^ Page Module:Citation/CS1/styles.css has no content.Blomquist, A. T.; Goldstein, Albert (1956). "1,2-Cyclodecanediol". Organic Syntheses. 36: 12. doi:10.15227/orgsyn.036.0012.
- ^ Page Module:Citation/CS1/styles.css has no content.R. H. Manske (1934). "Decamethylene Glycol". Organic Syntheses. 14: 20. doi:10.15227/orgsyn.014.0020.
- ^ Page Module:Citation/CS1/styles.css has no content.Thody, A. J.; Shuster, S. (1989). "Control and Function of Sebaceous Glands". Physiological Reviews. 69 (2): 383–416. doi:10.1152/physrev.1989.69.2.383. PMID 2648418.
- ^ Page Module:Citation/CS1/styles.css has no content.Cheng JB, Russell DW (September 2004). "Mammalian Wax Biosynthesis II: Expression cloning of wax synthase cDNAs encoding a member of the acyltransferase enzyme family" (PDF). The Journal of Biological Chemistry. 279 (36): 37798–807. doi:10.1074/jbc.M406226200. PMC 2743083. PMID 15220349. Archived from the original (PDF) on 2006-07-06. Retrieved 2020-08-03.
- ^ Page Module:Citation/CS1/styles.css has no content.Powell WS, Rokach J (March 2020). "Targeting the OXE receptor as a potential novel therapy for asthma". Biochemical Pharmacology. 179 113930. doi:10.1016/j.bcp.2020.113930. PMC 10656995. PMID 32240653. S2CID 214768793.
Template:Navbox linear saturated dicarboxylic acids
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