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Sapienic acid

16:1ω10 16:1n10 (lipid numbers)

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. 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, and sapienic acid has potent antibacterial activity against pathogens like Staphylococcus aureus. Reduced omega-3 intake has been linked to lower sapienic acid levels in sebum.

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.

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

References

References

  1. (May 2005). "Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis". Nature Publishing Group.
  2. (2005). "Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus". Dermatology.
  3. Webster, Guy F.. (2007). "Acne and Its Therapy". CRC Press.
  4. (March 2015). "The effect of skin fatty acids on Staphylococcus aureus". Archives of Microbiology.
  5. (February 2016). "Palmitic acid (16:0) competes with omega-6 linoleic and omega-3 ɑ-linolenic acids for FADS2 mediated Δ6-desaturation". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids.
  6. (January 2002). "Metabolic fate and selective utilization of major fatty acids in human sebaceous gland". Nature Publishing Group.
  7. (May 2003). "Identification of the delta-6 desaturase of human sebaceous glands: expression and enzyme activity". Nature Publishing Group.
  8. (13 April 2010). "Reactions of ozone with human skin lipids: Sources of carbonyls, dicarbonyls, and hydroxycarbonyls in indoor air". Proceedings of the National Academy of Sciences.
  9. (26 May 2022). "Mosquito brains encode unique features of human odour to drive host seeking". Nature.
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