Stable analogs of 13‑hydroxy-9,10-trans-epoxy-(11E)-octadecenoate (13,9-HEL), an oxidized derivative of linoleic acid implicated in the epidermal skin barrier.
Hydroxy-epoxy- and trihydroxy derivatives of linoleic acid are proposed to play an essential function in formation of the mammalian skin permeability barrier, which could account for the essential nature of its precursor, linoleic acid. Recent literature suggests that a specific oxidized enone derivative of LA esterified in ceramides facilitates binding to proteins, potentially serving a structural role in formation of the epidermal skin barrier. However, it is still to be established if other linoleic acid derivatives are also required for skin barrier formation, and whether the essential role is performed exclusively by an esterified, structural lipid or as an unesterified, labile signaling lipid, or by some combination of these derivatives. Progress in this domain is limited by lack of availability of hydroxy‑epoxy-and trihydroxy- and octadecenoate derivatives of linoleic acid and related compounds, and challenges in maintaining them in the unesterified lipid pool. Here we describe methods for the total synthesis of hydroxy‑epoxy-octadecenoate derivatives of linoleic acid (HEL
Published In/Presented At
Keyes, G. S., Maiden, K., & Ramsden, C. E. (2021). Stable analogs of 13‑hydroxy-9,10-trans-epoxy-(11E)-octadecenoate (13,9-HEL), an oxidized derivative of linoleic acid implicated in the epidermal skin barrier. Prostaglandins, leukotrienes, and essential fatty acids, 174, 102357. https://doi.org/10.1016/j.plefa.2021.102357
Medicine and Health Sciences
Department of Obstetrics and Gynecology, Department of Obstetrics and Gynecology Residents, Fellows and Residents