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Sapienic acid

Sapienic acid
Names
Preferred IUPAC name
(6Z)-Hexadec-6-enoic acid
Other names
cis-6-Hexadecenoic acid
16:1ω10
16:1n10 (lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=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- ☒N
    Key: NNNVXFKZMRGJPM-KHPPLWFESA-N ☒N
  • 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-
    Key: NNNVXFKZMRGJPM-KHPPLWFEBD
  • O=C(O)CCCC\C=C/CCCCCCCCC
Properties
C16H30O2
Molar mass 254.414 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1] 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,[2] and sapienic acid has potent antibacterial activity against pathogens like Staphylococcus aureus.[3][4] Reduced omega-3 intake has been linked to lower sapienic acid levels in sebum.[5]

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.[6][7] A two-carbon extension product of sapienic acid, sebaleic acid, is also present in sebum. Sapienic acid can lead to the decanal which is likely what mosquitoes use to identify human prey.[8]

References

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  1. ^ Katsuta Y, Iida T, Inomata S, Denda M (May 2005). "Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis". The Journal of Investigative Dermatology. 124 (5). Nature Publishing Group: 1008–13. doi:10.1111/j.0022-202X.2005.23682.x. PMID 15854043.
  2. ^ Takigawa H, Nakagawa H, Kuzukawa M, Mori H, Imokawa G (2005). "Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus". Dermatology. 211 (3): 240–8. doi:10.1159/000087018. PMID 16205069. S2CID 1574784.
  3. ^ Webster GF, Anthony V. Rawlings (2007). Acne and Its Therapy. Basic and clinical dermatology. Vol. 40. CRC Press. p. 311. ISBN 978-0-8247-2971-4.
  4. ^ Neumann Y, Ohlsen K, Donat S, Engelmann S, Kusch H, Albrecht D, et al. (March 2015). "The effect of skin fatty acids on Staphylococcus aureus". Archives of Microbiology. 197 (2): 245–67. Bibcode:2015ArMic.197..245N. doi:10.1007/s00203-014-1048-1. PMC 4326651. PMID 25325933.
  5. ^ Park HG, Kothapalli KS, Park WJ, DeAllie C, Liu L, Liang A, et al. (February 2016). "Palmitic acid (16:0) competes with omega-6 linoleic and omega-3 ɑ-linolenic acids for FADS2 mediated Δ6-desaturation". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1861 (2): 91–97. doi:10.1016/j.bbalip.2015.11.007. PMC 4691389. PMID 26597785.
  6. ^ Pappas A, Anthonavage M, Gordon JS (January 2002). "Metabolic fate and selective utilization of major fatty acids in human sebaceous gland". The Journal of Investigative Dermatology. 118 (1). Nature Publishing Group: 164–71. doi:10.1046/j.0022-202x.2001.01612.x. PMID 11851890.
  7. ^ Ge L, Gordon JS, Hsuan C, Stenn K, Prouty SM (May 2003). "Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity". The Journal of Investigative Dermatology. 120 (5). Nature Publishing Group: 707–14. doi:10.1046/j.1523-1747.2003.12123.x. PMID 12713571.
  8. ^ Zhao Z, Zung JL, Kriete AL, Iqbal A, Younger MA, Matthews BJ, Merhof D, Thiberge S, Strauch M, McBride CS (2020). "Chemical signatures of human odour generate a unique neural code in the brain of Aedes aegypti mosquitoes" (PDF). doi:10.1101/2020.11.01.363861. S2CID 226263862. {{cite journal}}: Cite journal requires |journal= (help)
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