Sebacic acid

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Sebacic acid
Sebacic acid.svg
Sebacic acid 3D ball.png
Names
Preferred IUPAC name
Decanedioic acid
Other names
1,8-Octanedicarboxylic acid
Decane-1,10-dioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.496 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-845-5
MeSH C011107
PubChem CID
UNII
  • 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) X mark.svgN
    Key: CXMXRPHRNRROMY-UHFFFAOYSA-N X mark.svgN
  • 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
  • OC(=O)CCCCCCCCC(=O)O
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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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]

Contents

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 tertiary hydroperoxide, which gives cyclodecenone, a precursor to sebacic acid. [3]

Sebacic acid has also been produced commercially by Kolbe electrolysis of adipic acid. [4]

Conversion of dimethyl ester of sebacic acid to cyclodecanediol by acyloin condensation followed by hydrogenation using a copper chromite catalyst. Me2sabacateTocycloC10diol.svg
Conversion of dimethyl ester of sebacic acid to cyclodecanediol by acyloin condensation followed by hydrogenation using a copper chromite catalyst.

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%). [6] [7] 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. [8]

Related Research Articles

<span class="mw-page-title-main">Wax</span> Class of organic compounds which are malleable at room temperature

Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in nonpolar organic solvents such as hexane, benzene and chloroform. Natural waxes of different types are produced by plants and animals and occur in petroleum.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Tallow</span> Rendered form of beef or mutton fat

Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides.

<span class="mw-page-title-main">Stearin</span> Chemical compound

Stearin, or tristearin, or glyceryl tristearate is an odourless, white powder. It is a triglyceride derived from three units of stearic acid. Most triglycerides are derived from at least two and more commonly three different fatty acids. Like other triglycerides, stearin can crystallise in three polymorphs. For stearin, these melt at 54 (α-form), 65, and 72.5 °C (β-form).

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C (156.9 °F) °C and a pKa of 4.50.

<span class="mw-page-title-main">Acenaphthene</span> Chemical compound

Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound.

Dodecanol, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in shampoos. Dodecanol is tasteless, colorless, and has a floral odor.

In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups. The general molecular formula for dicarboxylic acids can be written as HO2C−R−CO2H, where R can be aliphatic or aromatic. In general, dicarboxylic acids show similar chemical behavior and reactivity to monocarboxylic acids.

<span class="mw-page-title-main">Azelaic acid</span> Organic chemical compound

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. AzA inhibits tyrosinase.

<span class="mw-page-title-main">Jojoba oil</span> Oil extracted from jojoba seeds

Jojoba oil is the liquid produced in the seed of the Simmondsia chinensis (jojoba) plant, a shrub, which is native to southern Arizona, southern California, and northwestern Mexico. The oil makes up approximately 50% of the jojoba seed by weight. The terms "jojoba oil" and "jojoba wax" are often used interchangeably because the wax visually appears to be a mobile oil, but as a wax it is composed almost entirely (~97%) of mono-esters of long-chain fatty acids (wax ester) and alcohols, accompanied by only a tiny fraction of triglyceride esters. This composition accounts for its extreme shelf-life stability and extraordinary resistance to high temperatures, compared with true vegetable oils.

Higher alkanes are alkanes having nine or more carbon atoms. Nonane is the lightest alkane to have a flash point above 25 °C, and is not classified as dangerously flammable.

Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.

Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

<span class="mw-page-title-main">Ricinoleic acid</span> Chemical compound

Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid, is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of castor plant, the plant that produces ricin. It is also found in the sclerotium of ergot. About 90% of the fatty acid content in castor oil is the ricinolein.

A feed additive is an additive of extra nutrient or drug for livestock. Such additives include vitamins, amino acids, fatty acids, minerals, pharmaceutical, fungal products and steroidal compounds. The additives might impact feed presentation, hygiene, digestibility, or effect on intestinal health.

Lithium stearate is a chemical compound with the formula LiO2C(CH2)16CH3. It is formally classified as a soap (a salt of a fatty acid). Lithium stearate is a white soft solid, prepared by the reaction of lithium hydroxide and stearic acid.

Lithium 12-hydroxystearate (C18H35LiO3) is a chemical compound classified as a lithium soap. In chemistry, "soap" refers to salts of fatty acids. Lithium 12-hydroxystearate is a white solid. Lithium soaps are key component of many lubricating greases.

A metallic soap is a metallic salt of a fatty acid. Theoretically, soaps can be made of any metal, although not all enjoy practical uses. Varying the metal can strongly affect the properties of the compound, particularly its solubility.

<span class="mw-page-title-main">2-Octanol</span> Chemical compound

2-Octanol is an organic compound with the chemical formula CH3CH(OH)(CH2)5CH3. It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is chiral.

Brassylic acid is an organic compound with chemical formula (CH2)11(CO2H)2. A white solid, it is the C13-dicarboxylic acid. It is prepared by oxidation of erucic acid, which is abundant in some seed oils. Pelargonic acid is the coproduct. In the industrial setting, brassylic acid is used to produce specialty nylons, e.g. nylon 1313.

References

  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.
  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. ISBN   3527306730.
  3. ↑ Griesbaum, Karl; Behr, Arno; Biedenkapp, Dieter; Voges, Heinz-Werner; Garbe, Dorothea; Paetz, Christian; Collin, Gerd; Mayer, Dieter; Höke, Hartmut (2000). "Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_227. ISBN   3527306730.
  4. ↑ Seko, Maomi; Yomiyama, Akira; Isoya, Toshiro (1979). "Development of Kolbe Electrosynthesis of Sebacic Acid". CEER, Chemical Economy & Engineering Review. 11 (9): 48-50.
  5. ↑ Blomquist, A. T.; Goldstein, Albert (1956). "1,2-Cyclodecanediol". Organic Syntheses. 36: 12. doi:10.15227/orgsyn.036.0012.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
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