Chemistry:Sapienic acid
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| Names | |
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| Preferred IUPAC name
(6Z)-Hexadec-6-enoic acid | |
| Other names
cis-6-Hexadecenoic acid
16:1ω10 16:1n10 (lipid numbers) | |
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3D model (JSmol)
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| 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). | |
 verify (what is   ?)
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| Infobox references | |
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
- ↑ "Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis". The Journal of Investigative Dermatology (Nature Publishing Group) 124 (5): 1008–13. May 2005. doi:10.1111/j.0022-202X.2005.23682.x. PMID 15854043.
- ↑ "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. 2005. doi:10.1159/000087018. PMID 16205069. https://www.karger.com/Article/FullText/87018.
- ↑ Webster, Guy F.; Anthony V. Rawlings (2007). Acne and Its Therapy. Basic and clinical dermatology. 40. CRC Press. pp. 311. ISBN 978-0-8247-2971-4.
- ↑ "The effect of skin fatty acids on Staphylococcus aureus". Archives of Microbiology 197 (2): 245–67. March 2015. doi:10.1007/s00203-014-1048-1. PMID 25325933. Bibcode: 2015ArMic.197..245N.
- ↑ "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. February 2016. doi:10.1016/j.bbalip.2015.11.007. PMID 26597785.
- ↑ "Metabolic fate and selective utilization of major fatty acids in human sebaceous gland". The Journal of Investigative Dermatology (Nature Publishing Group) 118 (1): 164–71. January 2002. doi:10.1046/j.0022-202x.2001.01612.x. PMID 11851890.
- ↑ "Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity". The Journal of Investigative Dermatology (Nature Publishing Group) 120 (5): 707–14. May 2003. doi:10.1046/j.1523-1747.2003.12123.x. PMID 12713571.
- ↑ Zhao, Zhilei; Zung, Jessica L.; Kriete, Alexis L.; Iqbal, Azwad; Younger, Meg A.; Matthews, Benjamin J.; Merhof, Dorit; Thiberge, Stephan et al. (2020). Chemical signatures of human odour generate a unique neural code in the brain of Aedes aegypti mosquitoes. doi:10.1101/2020.11.01.363861. https://www.biorxiv.org/content/10.1101/2020.11.01.363861v1.full.pdf.
External links
- Waxes, The Lipid Library
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