sapienic acid

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{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 428772087

| ImageFile = Sapienic acid.svg

| ImageSize = 200px

| PIN = (6Z)-Hexadec-6-enoic acid

| OtherNames = cis-6-Hexadecenoic acid
16:1ω10
16:1n10 (lipid numbers)

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 17004-51-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6460S1EJ28

| SMILES = O=C(O)CCCC\C=C/CCCCCCCCC

| PubChem = 5312419

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 76244

| KEGG = C21942

| 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

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|Section3={{Chembox Hazards

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Sapienic acid is a fatty acid that is a major component of human sebum. Unique to humans, it takes its scientific name from the root sapiens. The equivalent fatty acid in mouse sebum is palmitoleic acid.{{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 }} Sapienic acid salts, esters, anion, and conjugate base are known as sapienates.

Deficient production of sapienic acid has been implicated in the development of atopic dermatitis,{{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 | url-access = subscription }} and sapienic acid has potent antibacterial activity against pathogens like Staphylococcus aureus.{{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}}{{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 = }} Reduced omega-3 intake has been linked to lower sapienic acid levels in sebum.{{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 = }}

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.{{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 }}{{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 }} A two-carbon extension product of sapienic acid, sebaleic acid, is also present in sebum.

Decanal, which can be formed through the breakdown of sapienic acid,{{cite journal |last1=Wisthaler |first1=Armin |last2=Weschler |first2=Charles J. |title=Reactions of ozone with human skin lipids: Sources of carbonyls, dicarbonyls, and hydroxycarbonyls in indoor air |journal=Proceedings of the National Academy of Sciences |date=13 April 2010 |volume=107 |issue=15 |pages=6568–6575 |doi=10.1073/pnas.0904498106 |pmid=19706436 |url=https://pmc.ncbi.nlm.nih.gov/articles/PMC2872416/ |access-date=26 May 2025}} is likely what mosquitoes use to identify human prey.{{cite journal |last1=Zhao |first1=Zhilei |last2=Zung |first2=Jessica L. |last3=Hinze |first3=Annika |last4=Kriete |first4=Alexis L. |last5=Iqbal |first5=Azwad |last6=Younger |first6=Meg A. |last7=Matthews |first7=Benjamin J. |last8=Merhof |first8=Dorit |last9=Thiberge |first9=Stephan |last10=Ignell |first10=Rickard |last11=Strauch |first11=Martin |last12=McBride |first12=Carolyn S. |title=Mosquito brains encode unique features of human odour to drive host seeking |journal=Nature |date=26 May 2022 |volume=605 |issue=7911 |pages=706–712 |doi=10.1038/s41586-022-04675-4 |pmid=35508661 |url=https://pubmed.ncbi.nlm.nih.gov/35508661/ |access-date=26 May 2025}}