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| Names | |
|---|---|
| IUPAC name (Z)-6-Hexadecenoic acid | |
| Other names cis-6-Hexadecenoic acid; 16:1ω10 | |
| Identifiers | |
| CAS Number | |
| 3D model (JSmol) | |
| CompTox Dashboard (EPA) | |
SMILES
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| Properties | |
| Chemical formula | C16H30O2 |
| Molar mass | 254.414 g·mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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Sapienic acid (16:1, n-10, cis-6 hexadecenoic, or sapienate) is a fatty acid that is a major component of human sebum. Among hair-bearing animals, sapienic acid is unique to humans (thus sapien is the root of its name). 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.
References
- Katsuta, Yuji (2005). "Unsaturated Fatty Acids Induce Calcium Influx into Keratinocytes and Cause Abnormal Differentiation of Epidermis". Journal of Investigative Dermatology. 124 (5). Nature Publishing Group: 1008–1013. doi:10.1111/j.0022-202X.2005.23682.x. PMID 15854043.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - Webster, Guy F. (2007). Acne and Its Therapy. Basic and clinical dermatology. Vol. 40. CRC Press. p. 311. ISBN 0824729714.
{{cite book}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - Drake, David R. (January 2008). "Antimicrobial lipids at the skin surface". Journal of Lipid Research. 49 (1). American Society for Biochemistry and Molecular Biology: 4–11. doi:10.1194/jlr.R700016-JLR200. ISSN 1539-7262. PMID 17906220.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help)CS1 maint: unflagged free DOI (link) - Pappas, Apostolos (2002). "Metabolic Fate and Selective Utilization of Major Fatty Acids in Human Sebaceous Gland". Journal of Investigative Dermatology. 118 (1). Nature Publishing Group: 164–171. doi:10.1046/j.0022-202x.2001.01612.x. ISSN 1523-1747. PMID 11851890.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - Ge, Lan (2003). "Identification of the Delta-6 Desaturase of Human Sebaceous Glands: Expression and Enzyme Activity". Journal of Investigative Dermatology. 120 (5). Nature Publishing Group: 707–714. doi:10.1046/j.1523-1747.2003.12123.x. ISSN 1523-1747. PMID 12713571.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help)
External links
- Waxes, The Lipid Library