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Sapienic acid: Difference between revisions

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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 06:36, 20 January 2025 edit undo193.233.107.15 (talk)No edit summary 
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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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| 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-
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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 ] 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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