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Sapienic acid

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Sapienic acid
Names
IUPAC name
(Z)-6-Hexadecenoic acid
Other names
cis-6-Hexadecenoic acid; 16:1ω10
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • O=C(O)CCCC\C=C/CCCCCCCCC
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).
☒N verify (what is checkY☒N ?)

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.[1] Sapienic acid has been implicated in the development of acne,[2] and it may have potent antibacterial activity.[3]

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.[4][5] A two-carbon extension product of sapienic acid, sebaleic acid, is also present in sebum.

References

  1. ^ Katsuta, Yuji; Toshii Iida; Shinji Inomata; Mitsuhiro Denda (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.
  2. ^ Webster, Guy F.; Anthony V. Rawlings (2007). Acne and Its Therapy. Basic and clinical dermatology. Vol. 40. CRC Press. p. 311. ISBN 978-0-8247-2971-4.
  3. ^ Drake, David R.; Kim A. Brogden; Deborah V. Dawson; Philip W. Wertz (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.
  4. ^ Pappas, Apostolos; Michael Anthonavage; Joel S Gordon (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.
  5. ^ Ge, Lan; Joel S Gordon; Charleen Hsuan; Kurt Stenn; Stephen M Prouty (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.

External links


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