Sebacic acid

Sebacic acid
Names
	Preferred IUPAC name Decanedioic acid
	Other names 1,8-Octanedicarboxylic acid; Decane-1,10-dioic acid;
Identifiers
CAS Number	111-20-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:41865 ;
ChemSpider	5004 ;
ECHA InfoCard	100.003.496
EC Number	203-845-5;
MeSH	C011107
PubChem CID	5192;
UNII	97AN39ICTC ;
CompTox Dashboard (EPA)	DTXSID7026867 ;
	InChI 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) Key: CXMXRPHRNRROMY-UHFFFAOYSA-N ; InChI=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-UHFFFAOYAE;
	SMILES OC(=O)CCCCCCCCC(=O)O;
Properties
Chemical formula	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
Solubility in water	0.25 g/L
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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	Infobox references

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical 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.^[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.

Production

Sebacic acid is produced from castor oil by cleavage of ricinoleic acid, which is obtained from castor oil. Octanol & 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

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 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, 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

1 2 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.
1 2 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; Höke (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.

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[pka-1] 1 2 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.

[Ullmanns-2] 1 2 Cornils, Boy; Lappe, Peter (2000). "Dicarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a08_523.

[Ull-3] Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227.

[THODY1989-4] 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.

[CHENG2004-5] 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.

[pmid32240653-6] 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.

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