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
CAS Number	17004-51-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:76244 N
ChemSpider	4471844 N
KEGG	C21942
PubChem CID	5312419
UNII	6460S1EJ28 Y
CompTox Dashboard (EPA)	DTXSID50904584
InChI 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
SMILES O=C(O)CCCC\C=C/CCCCCCCCC
Properties
Chemical formula	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). N verify (what is YN ?) 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.

Decanal, which can be formed through the breakdown of sapienic acid,^[8] is likely what mosquitoes use to identify human prey.^[9]