Sebacic acid: Difference between revisions
imported>Aadirulez8 m v2.05 - Auto / Fix errors for CW project (Template value ends with break) |
imported>InternetArchiveBot Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.9.5 |
||
| Line 5: | Line 5: | ||
| Name = Sebacic acid | | Name = Sebacic acid | ||
| ImageFile = Sebacic_acid.svg | | ImageFile = Sebacic_acid.svg | ||
| ImageClass = skin-invert | |||
| ImageSize = 260px | | ImageSize = 260px | ||
| ImageAlt = Skeletal formula of sebacic acid | | ImageAlt = Skeletal formula of sebacic acid | ||
| ImageFile1 = Sebacic acid 3D ball.png | | ImageFile1 = Sebacic acid 3D ball.png | ||
| ImageClass1 = bg-transparent | |||
| ImageSize1 = 250px | | ImageSize1 = 250px | ||
| ImageAlt1 = Ball-and-stick model of the sebacic acid molecule | | ImageAlt1 = Ball-and-stick model of the sebacic acid molecule | ||
| PIN = Decanedioic acid | | PIN = Decanedioic acid | ||
| OtherNames = 1,8-Octanedicarboxylic acid<br>Decane-1,10-dioic acid | | OtherNames = 1,8-Octanedicarboxylic acid<br />Decane-1,10-dioic acid | ||
|Section1={{Chembox Identifiers | |Section1={{Chembox Identifiers | ||
| CASNo_Ref = {{cascite|correct|CAS}} | | CASNo_Ref = {{cascite|correct|CAS}} | ||
| Line 61: | Line 63: | ||
==Potential medical significance== | ==Potential medical significance== | ||
Sebum is a secretion by skin [[sebaceous gland]]s. It is a [[wax|waxy]] set of [[lipids]] composed of [[triglycerides]] (≈41%), [[wax esters]] (≈26%), [[squalene]] (≈12%), and [[fatty acids#Free fatty acids|free fatty acids]] (≈16%).<ref name=THODY1989>{{cite journal |last1=Thody |first1=A. J. |first2=S. |last2=Shuster |title=Control and Function of Sebaceous Glands |journal=Physiological Reviews |volume=69 |issue=2 |year=1989 |pages=383–416 |doi= 10.1152/physrev.1989.69.2.383|pmid=2648418 }}</ref><ref name=CHENG2004>{{cite journal |vauthors=Cheng JB, Russell DW |title=Mammalian Wax Biosynthesis II: Expression cloning of wax synthase cDNAs encoding a member of the acyltransferase enzyme family |journal=The Journal of Biological Chemistry |volume=279 |issue=36 |pages=37798–807 |date=September 2004 |pmid=15220349 |pmc=2743083 |doi=10.1074/jbc.M406226200 |url=http://www4.utsouthwestern.edu/moleculargenetics/pdf/dr_cur_res/JBiolChem2004-II.pdf|doi-access=free }}</ref> Included in the free fatty acid secretions in sebum are [[polyunsaturated fatty acid]]s 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., {{chem name|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.<ref name="pmid32240653">{{cite journal | vauthors = Powell WS, Rokach J | title = Targeting the OXE receptor as a potential novel therapy for asthma | journal = Biochemical Pharmacology | | Sebum is a secretion by skin [[sebaceous gland]]s. It is a [[wax|waxy]] set of [[lipids]] composed of [[triglycerides]] (≈41%), [[wax esters]] (≈26%), [[squalene]] (≈12%), and [[fatty acids#Free fatty acids|free fatty acids]] (≈16%).<ref name=THODY1989>{{cite journal |last1=Thody |first1=A. J. |first2=S. |last2=Shuster |title=Control and Function of Sebaceous Glands |journal=Physiological Reviews |volume=69 |issue=2 |year=1989 |pages=383–416 |doi= 10.1152/physrev.1989.69.2.383|pmid=2648418 }}</ref><ref name=CHENG2004>{{cite journal |vauthors=Cheng JB, Russell DW |title=Mammalian Wax Biosynthesis II: Expression cloning of wax synthase cDNAs encoding a member of the acyltransferase enzyme family |journal=The Journal of Biological Chemistry |volume=279 |issue=36 |pages=37798–807 |date=September 2004 |pmid=15220349 |pmc=2743083 |doi=10.1074/jbc.M406226200 |url=http://www4.utsouthwestern.edu/moleculargenetics/pdf/dr_cur_res/JBiolChem2004-II.pdf |doi-access=free |archive-date=2006-07-06 |access-date=2020-08-03 |archive-url=https://web.archive.org/web/20060706075548/http://www4.utsouthwestern.edu/moleculargenetics/pdf/dr_cur_res/JBiolChem2004-II.pdf |url-status=dead }}</ref> Included in the free fatty acid secretions in sebum are [[polyunsaturated fatty acid]]s 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., {{chem name|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.<ref name="pmid32240653">{{cite journal | vauthors = Powell WS, Rokach J | title = Targeting the OXE receptor as a potential novel therapy for asthma | journal = Biochemical Pharmacology | article-number = 113930 | date = March 2020 | volume = 179 | pmid = 32240653 | doi = 10.1016/j.bcp.2020.113930 | s2cid = 214768793 | pmc = 10656995 }}</ref> | ||
==References== | ==References== | ||
Latest revision as of 10:17, 8 December 2025
<templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| MeSH | C011107 |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Density | 1.209 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
| Acidity (pKa) | 4.720, 5.450[1] |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula Template:Chem2. 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]
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., 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.[8]
References
<templatestyles src="Reflist/styles.css" />
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ a b Template:Ullmann
- ↑ Template:Ullmann
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
Script error: No such module "Check for unknown parameters".