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Sapienic acid

Sapienic acid
Sapienic acid.svg
Names
IUPAC name
(Z)-6-Hexadecenoic acid
Other names
cis-6-Hexadecenoic acid; 16:1ω10
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
Properties
C16H30O2
Molar mass 254.41 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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Infobox references

Sapienic acid (16:1, n-10, cis-6 hexadecenoic, or sapienate) is a fatty acid that is a major component of human sebum. Sapienic acid is a sebum fatty acid that is unique to humans (from whose scientific name it takes the root sapiens). The equivalent fatty acid in mouse sebum is palmitoleic acid. Sapienic acid has been implicated in the development of acne, and it may have potent antibacterial activity.

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



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