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Names | |
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Preferred IUPAC name
(6Z)-Hexadec-6-enoic acid | |
Other names | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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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]