Sapienic acid

Sapienic acid
IUPAC name

(Z)-6-Hexadecenoic acid
Other names

cis-6-Hexadecenoic acid; 16:1ω10
Identifiers
CAS number 17004-51-2
Jmol-3D images Image 1
Properties
Molecular formula C16H30O2
Molar mass 254.41 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. 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.[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 and Mitsuhiro Denda (2005). "Unsaturated Fatty Acids Induce Calcium Influx into Keratinocytes and Cause Abnormal Differentiation of Epidermis". Journal of Investigative Dermatology (Nature Publishing Group) 124 (5): 1008–1013. doi:10.1111/j.0022-202X.2005.23682.x. PMID 15854043. http://www.nature.com/jid/journal/v124/n5/full/5602810a.html. 
  2. ^ Webster, Guy F.; Anthony V. Rawlings (2007). Acne and Its Therapy. Basic and clinical dermatology. 40. CRC Press. pp. 311. ISBN 0824729714. 
  3. ^ Drake, David R.; Kim A. Brogden, Deborah V. Dawson and Philip W. Wertz (January 2008). "Antimicrobial lipids at the skin surface". Journal of Lipid Research (American Society for Biochemistry and Molecular Biology) 49 (1): 4–11. doi:10.1194/jlr.R700016-JLR200. ISSN 1539-7262. PMID 17906220. http://www.jlr.org/cgi/content/full/49/1/4. 
  4. ^ Pappas, Apostolos; Michael Anthonavage and Joel S Gordon (2002). "Metabolic Fate and Selective Utilization of Major Fatty Acids in Human Sebaceous Gland". Journal of Investigative Dermatology (Nature Publishing Group) 118 (1): 164–171. doi:10.1046/j.0022-202x.2001.01612.x. ISSN 1523-1747. PMID 11851890. http://www.nature.com/jid/journal/v118/n1/full/5601374a.html. 
  5. ^ Ge, Lan; Joel S Gordon, Charleen Hsuan, Kurt Stenn and Stephen M Prouty (2003). "Identification of the Delta-6 Desaturase of Human Sebaceous Glands: Expression and Enzyme Activity". Journal of Investigative Dermatology (Nature Publishing Group) 120 (5): 707–714. doi:10.1046/j.1523-1747.2003.12123.x. ISSN 1523-1747. PMID 12713571. http://www.nature.com/jid/journal/v120/n5/full/5601793a.html. 

External links

Saturated
VFA: Acetic (C2) · Propionic (C3) · Butyric (C4) · Valeric (C5) · Caproic (C6) · Enanthic (C7) · Caprylic (C8) · Pelargonic (C9) · Capric (C10) · Undecylic (C11) · Lauric (C12) · Tridecylic (C13) · Myristic (C14) · Pentadecanoic (C15) · Palmitic (C16) · Margaric (C17) · Stearic (C18) · Nonadecylic (C19) · Arachidic (C20) · Heneicosylic (C21) · Behenic (C22) · Tricosylic (C23) · Lignoceric (C24) · Pentacosylic (C25) · Cerotic (C26) · Heptacosylic (C27) · Montanic (C28) · Nonacosylic (C29) · Melissic (C30) · Hentriacontylic (C31) · Lacceroic (C32) · Psyllic (C33) · Geddic (C34) · Ceroplastic (C35) · Hexatriacontylic (C36)
n−3 Unsaturated
n−6 Unsaturated
n−9 Unsaturated
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i