| 词条 | Sapienic acid |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 428772087 | ImageFile = Sapienic acid.svg | ImageSize = 200px | IUPACName = (Z)-6-Hexadecenoic acid | OtherNames = cis-6-Hexadecenoic acid; 16:1ω10 |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|??}} | CASNo = 17004-51-2 | SMILES = O=C(O)CCCC\\C=C/CCCCCCCCC | PubChem = 5312419 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 76244 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4471844 | InChI = 1/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10- | InChIKey = NNNVXFKZMRGJPM-KHPPLWFEBD | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h10-11H,2-9,12-15H2,1H3,(H,17,18)/b11-10- | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = NNNVXFKZMRGJPM-KHPPLWFESA-N }} |Section2={{Chembox Properties | C=16 | H=30 | O=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}Sapienic acid (16:1, n-10, cis-6 hexadecenoic, or sapienate) is a fatty acid that is a major component of human sebum. Sapienic acid is a sebum fatty acid that is unique to humans (from whose scientific name it takes the root sapiens). The equivalent fatty acid in mouse sebum is palmitoleic acid.[1] Sapienic acid has been implicated in the development of acne,[2] and it may have potent antibacterial activity.[3] Delta-6-desaturation of palmitic acid leads to the biosynthesis of sapienic acid. In other tissues linoleic acid is the target for delta 6 desaturase, but linoleic acid is degraded in sebaceous cells, allowing the enzyme to desaturate palmitic to sapienic acid.[4][5] A two-carbon extension product of sapienic acid, sebaleic acid, is also present in sebum. References1. ^{{cite journal|last=Katsuta|first=Yuji |author2=Toshii Iida |author3=Shinji Inomata |author4=Mitsuhiro Denda|year=2005|title=Unsaturated Fatty Acids Induce Calcium Influx into Keratinocytes and Cause Abnormal Differentiation of Epidermis|journal=Journal of Investigative Dermatology|publisher=Nature Publishing Group|volume=124|pages=1008–1013|url=http://www.nature.com/jid/journal/v124/n5/full/5602810a.html|doi=10.1111/j.0022-202X.2005.23682.x|pmid=15854043|issue=5}} 2. ^{{cite book|last=Webster|first=Guy F.|author2=Anthony V. Rawlings |title=Acne and Its Therapy|publisher=CRC Press|year=2007|series=Basic and clinical dermatology|volume=40|pages=311|isbn=0-8247-2971-4}} 3. ^{{cite journal|last=Drake|first=David R. |author2=Kim A. Brogden |author3=Deborah V. Dawson |author4=Philip W. Wertz|date=January 2008|title=Antimicrobial lipids at the skin surface|journal=Journal of Lipid Research|publisher=American Society for Biochemistry and Molecular Biology|volume=49|pages=4–11|issn=1539-7262|url=http://www.jlr.org/cgi/content/full/49/1/4|pmid=17906220|doi=10.1194/jlr.R700016-JLR200|issue=1}} 4. ^{{cite journal|last=Pappas|first=Apostolos |author2=Michael Anthonavage |author3=Joel S Gordon|year=2002|title=Metabolic Fate and Selective Utilization of Major Fatty Acids in Human Sebaceous Gland|journal=Journal of Investigative Dermatology|publisher=Nature Publishing Group|volume=118|pages=164–171|issn=1523-1747|url=http://www.nature.com/jid/journal/v118/n1/full/5601374a.html|doi=10.1046/j.0022-202x.2001.01612.x|pmid=11851890|issue=1}} 5. ^{{cite journal|last=Ge|first=Lan |author2=Joel S Gordon |author3=Charleen Hsuan |author4=Kurt Stenn |author5=Stephen M Prouty|year=2003|title=Identification of the Delta-6 Desaturase of Human Sebaceous Glands: Expression and Enzyme Activity|journal=Journal of Investigative Dermatology|publisher=Nature Publishing Group|volume=120|pages=707–714|issn=1523-1747|url=http://www.nature.com/jid/journal/v120/n5/full/5601793a.html|doi=10.1046/j.1523-1747.2003.12123.x|pmid=12713571|issue=5}} External links
2 : Fatty acids|Alkenoic acids |
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