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Revision as of 15:51, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 20:46, 22 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits Added bibcode. Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. 
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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 359765948
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⚫ | verifiedrevid = 428772087
| ImageFile = Sapienic acid.svg | ImageFile = Sapienic acid.svg
| ImageSize = 200px | ImageSize = 200px
| IUPACName = (''Z'')-6-Hexadecenoic acid | PIN = (6''Z'')-Hexadec-6-enoic acid
| OtherNames = ''cis''-6-Hexadecenoic acid; 16:1ω10 | OtherNames = ''cis''-6-Hexadecenoic acid<br/>16:1ω10<br>16:1n10 (]s)
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
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| CASNo = 17004-51-2 | CASNo = 17004-51-2
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⚫ | PubChem =
| UNII = 6460S1EJ28
| SMILES = O=C(O)CCCC\C=C/CCCCCCCC | SMILES = O=C(O)CCCC\C=C/CCCCCCCCC
⚫ | PubChem = 5312419
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| ChEBI = 76244
| KEGG = C21942
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| 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-
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| C=16 | H=30 | O=2 | C=16 | H=30 | O=2
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| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
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'''Sapienic acid''' (16:1, n-10, cis-6 hexadecenoic, or sapienate) is a ] that is a major component of human ]. Among hair-bearing animals, sapienic acid is unique to humans (thus ] is the root of its name). The equivalent fatty acid in mouse sebum is ].<ref>{{cite journal|last=Katsuta|first=Yuji|coauthors=Toshii Iida, Shinji Inomata and 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}}</ref> Sapienic acid has been implicated in the development of ],<ref>{{cite book|last=Webster|first=Guy F.|coauthors=Anthony V. Rawlings|title=Acne and Its Therapy|publisher=CRC Press|year=2007|series=Basic and clinical dermatology|volume=40|pages=311|isbn=0824729714}}</ref> and it may have potent ] activity.<ref>{{cite journal|last=Drake|first=David R.|coauthors=Kim A. Brogden, Deborah V. Dawson and 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}}</ref> '''Sapienic acid''' is a ] that is a major component of human ]. Unique to humans, it takes its scientific name from the root ''sapiens''. The equivalent fatty acid in mouse sebum is ].<ref>{{cite journal | vauthors = Katsuta Y, Iida T, Inomata S, Denda M | title = Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis | journal = The Journal of Investigative Dermatology | volume = 124 | issue = 5 | pages = 1008–13 | date = May 2005 | pmid = 15854043 | doi = 10.1111/j.0022-202X.2005.23682.x | publisher = Nature Publishing Group | doi-access = free }}</ref> Sapienic acid ]s, ]s, ], and ] are known as sapienates.


Deficient production of sapienic acid has been implicated in the development of ],<ref>{{cite journal | vauthors = Takigawa H, Nakagawa H, Kuzukawa M, Mori H, Imokawa G | title = Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus | journal = Dermatology | volume = 211 | issue = 3 | pages = 240–8 | date = 2005 | pmid = 16205069 | doi = 10.1159/000087018 | s2cid = 1574784 | url = https://www.karger.com/Article/FullText/87018 }}</ref> and sapienic acid has potent ] activity against pathogens like ''].''<ref>{{cite book|last=Webster|first=Guy F.|title=Acne and Its Therapy|author2=Anthony V. Rawlings|publisher=CRC Press|year=2007|isbn=978-0-8247-2971-4|series=Basic and clinical dermatology|volume=40|pages=311}}</ref><ref>{{cite journal | vauthors = Neumann Y, Ohlsen K, Donat S, Engelmann S, Kusch H, Albrecht D, Cartron M, Hurd A, Foster SJ | display-authors = 6 | title = The effect of skin fatty acids on Staphylococcus aureus | journal = Archives of Microbiology | volume = 197 | issue = 2 | pages = 245–67 | date = March 2015 | pmid = 25325933 | pmc = 4326651 | doi = 10.1007/s00203-014-1048-1 | bibcode = 2015ArMic.197..245N | url = }}</ref> Reduced ] intake has been linked to lower sapienic acid levels in sebum.<ref>{{cite journal | vauthors = Park HG, Kothapalli KS, Park WJ, DeAllie C, Liu L, Liang A, Lawrence P, Brenna JT | display-authors = 6 | title = Palmitic acid (16:0) competes with omega-6 linoleic and omega-3 ɑ-linolenic acids for FADS2 mediated Δ6-desaturation | journal = Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids | volume = 1861 | issue = 2 | pages = 91–97 | date = February 2016 | pmid = 26597785 | pmc = 4691389 | doi = 10.1016/j.bbalip.2015.11.007 | url = }}</ref>
⚫ Delta 6 ] of ] leads to the biosynthesis of sapienic acid. In other tissues ] is the target for delta 6 desaturase, but linoleic acid is degraded in ]s, allowing the enzyme to desaturate palmitic to sapienic acid.<ref>{{cite journal|last=Pappas|first=Apostolos|coauthors=Michael Anthonavage and 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}}</ref><ref>{{cite journal|last=Ge|first=Lan|coauthors=Joel S Gordon, Charleen Hsuan, Kurt Stenn and 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}}</ref> A two-carbon extension product of sapienic acid, ], is also present in sebum.


⚫ ] of ] leads to the biosynthesis of sapienic acid. In other tissues ] is the target for delta 6 desaturase, but linoleic acid is degraded in ]s, allowing the enzyme to desaturate palmitic to sapienic acid.<ref>{{cite journal | vauthors = Pappas A, Anthonavage M, Gordon JS | title = Metabolic fate and selective utilization of major fatty acids in human sebaceous gland | journal = The Journal of Investigative Dermatology | volume = 118 | issue = 1 | pages = 164–71 | date = January 2002 | pmid = 11851890 | doi = 10.1046/j.0022-202x.2001.01612.x | publisher = Nature Publishing Group | doi-access = free }}</ref><ref>{{cite journal | vauthors = Ge L, Gordon JS, Hsuan C, Stenn K, Prouty SM | title = Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity | journal = The Journal of Investigative Dermatology | volume = 120 | issue = 5 | pages = 707–14 | date = May 2003 | pmid = 12713571 | doi = 10.1046/j.1523-1747.2003.12123.x | publisher = Nature Publishing Group | doi-access = free }}</ref> A two-carbon extension product of sapienic acid, ], is also present in sebum.
==References==
Sapienic acid can lead to the decanal which is likely what mosquitoes use to identify human prey.<ref>{{Cite journal|url=https://www.biorxiv.org/content/10.1101/2020.11.01.363861v1.full.pdf|doi=10.1101/2020.11.01.363861|title=Chemical signatures of human odour generate a unique neural code in the brain of Aedes aegypti mosquitoes|year=2020|last1=Zhao|first1=Zhilei|last2=Zung|first2=Jessica L.|last3=Kriete|first3=Alexis L.|last4=Iqbal|first4=Azwad|last5=Younger|first5=Meg A.|last6=Matthews|first6=Benjamin J.|last7=Merhof|first7=Dorit|last8=Thiberge|first8=Stephan|last9=Strauch|first9=Martin|last10=McBride|first10=Carolyn S.|s2cid=226263862}}</ref>
⚫ {{reflist}}


==External links== == References ==
⚫ {{reflist}}
⚫ *, The Lipid Library


== External links ==
⚫ *, The Lipid Library


{{fatty acids}} {{fatty acids}}


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