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.[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.
It can also be obtained from decalin via the tertiary hydroperoxide, which gives cyclodecenone, a precursor to sebacic acid.[3]
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%).[4][5] 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.[6]
Referencesedit
^ abBretti, 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.
^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.
^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. PMC2743083. PMID 15220349.
^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. PMID 32240653. S2CID 214768793.
November 23, 2023
sebacic, acid, naturally, occurring, dicarboxylic, acid, with, chemical, formula, ho2c, 8co2h, white, flake, powdered, solid, sebaceus, latin, tallow, candle, sebum, latin, tallow, refers, manufacture, candles, derivative, castor, namespreferred, iupac, name, . 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 2 Sebacic acid NamesPreferred IUPAC name Decanedioic acidOther names 1 8 Octanedicarboxylic acidDecane 1 10 dioic acidIdentifiersCAS Number 111 20 6 Y3D model JSmol Interactive imageChEBI CHEBI 41865 YChemSpider 5004 YECHA InfoCard 100 003 496EC Number 203 845 5MeSH C011107PubChem CID 5192UNII 97AN39ICTC YCompTox Dashboard EPA DTXSID7026867InChI InChI 1S C10H18O4 c11 9 12 7 5 3 1 2 4 6 8 10 13 14 h1 8H2 H 11 12 H 13 14 NKey CXMXRPHRNRROMY UHFFFAOYSA N NInChI 1 C10H18O4 c11 9 12 7 5 3 1 2 4 6 8 10 13 14 h1 8H2 H 11 12 H 13 14 Key CXMXRPHRNRROMY UHFFFAOYAESMILES OC O CCCCCCCCC O OPropertiesChemical formula C 10H 18O 4Molar mass 202 250 g mol 1Density 1 209 g cm3Melting 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 mmHgSolubility in water 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 N verify what is Y N Infobox references 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 editSebacic acid is produced from castor oil by cleavage of ricinoleic acid which is obtained from castor oil Octanol amp glycerin is a byproduct 2 It can also be obtained from decalin via the tertiary hydroperoxide which gives cyclodecenone a precursor to sebacic acid 3 Potential medical significance editSebum 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 4 5 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 6 References edit a b 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 Cornils Boy Lappe Peter 2000 Dicarboxylic Acids Aliphatic Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a08 523 Griesbaum Karl Behr Arno Biedenkapp Dieter Voges Heinz Werner Garbe Dorothea Paetz Christian Collin Gerd Mayer Dieter Hoke 2000 Hydrocarbons Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a13 227 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 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 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 PMID 32240653 S2CID 214768793 Retrieved from https en wikipedia org w index php title Sebacic acid amp oldid 1170851165, wikipedia, wiki, book, books, library,
