cis-6-Hexadecenoic Acid-d19 (Synonyms: C16:1(6Z)-d19, C16:1Δ6-d19, C16:1ω10c-d19, Sapienic Acid-d19)

cis-6-Hexadecenoic acid-d19 is intended for use as an internal standard for the quantification of cis-6-hexadecenoic acid by GC- or LC-MS. cis-6-Hexadecenoic acid is a monounsaturated fatty acid and is one of the primary fatty acids in human skin.1 cis-6-Hexadecenoic acid levels are increased in isolated sebum from the face and back of patients with acne.2 In contrast, levels are decreased in the non-lesional skin and isolated sebum of atopic dermatitis patients, which correlates with an increase in S. aureus in the sebum.1 It is active against S. aureus in vitro when used at a concentration of 5 μg/ml at pH 5.5.3 cis-6-Hexadecenoic acid disrupts membrane integrity, the proton motive force, increases membrane fluidity, and inhibits the electron transport chain in S. aureus.

References
1. Takigawa, H., Nakagawa, H., Kuzukawa, M., et al. 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 211(3), 240-248 (2005).
2. Li, W.-H., Zhang, Q., Flach, C.R., et al. In vitro modeling of unsaturated free fatty acid-mediated tissue impairments seen in acne lesions. Arch. Dermatol. Res. 309(7), 529-540 (2017).
3. Cartron, M.L., England, S.R., Chiriac, A.I., et al. Bactericidal activity of the human skin fatty acid cis-6-hexadecanoic acid on Staphylococcus aureus. Antimicrob. Agents Chemother. 58(7), 3599-3609 (2014).