title: Synthesis and characterization of O-acylated-ω-hydroxy fatty acids as skin-protecting barrier lipids.
abstract: A series of O-acylated-ω-hydroxy fatty acids (Acyl acids) of up to 34 carbons were synthesized and characterized through DSC, FTIR and Langmuir isotherm measurements to identify potential replacements to petrolatum, a highly used occlusive technology that if unrefined, it can potentially be classified as carcinogenic. Fourier transform infrared spectroscopy studies demonstrated that long acyl acids engender orthorhombic packing; packing behavior that is predominant in the lipid matrix of healthy stratum corneum, the outmost layer of the skin. In addition, Differential Scanning Calorimetry (DSC) and Langmuir isotherm studies suggested that the length of the hydrocarbon chain and the position of the ester bond influence the molecular organization of the acyl acids. For instance, 16-(tetradecanoyloxy)hexadecanoic acid (30 carbons) displayed a higher melting point (mp=68°C) than 10-(stearoyloxy)decanoic acid (28 carbons; mp=63°C) and 10-(tetradecanoyloxy)decanoic acid (24 carbons; mp=55°C) according to DSC. Moreover, Langmuir isotherm studies showed that mixtures of acyl acid with distearoylphosphatidylcholine improved packing behavior. Finally, Water Vapor Transmission Rate (WVTR) measurements showed that the compounds in fact decrease WVTR compared to untreated control (P<0.001) which demonstrates the potential of these ingredients as occlusive technologies to combat skin barrier diseases.
authors.affiliation: Department of Engineering, Aarhus University, Aarhus, Denmark.
authors.forename: B
authors.initials: B
authors.lastname: Pérez
authors.affiliation: Department of Engineering, Aarhus University, Aarhus, Denmark.
authors.forename: S E
authors.initials: SE
authors.lastname: Dahlgaard
authors.affiliation: New Product Research, GlaxoSmithKline Consumer Healthcare, Research Triangle Park, NC, 27709, USA.
authors.forename: P
authors.initials: P
authors.lastname: Bulsara
authors.affiliation: AVR Consulting Ltd, Northwich, Cheshire CW9 8FH, United Kingdom.
authors.forename: A V
authors.initials: AV
authors.lastname: Rawlings
authors.affiliation: Department of Chemistry, Aarhus University, Aarhus, Denmark; Interdisciplinary Nanoscience Center, Aarhus University, Aarhus, Denmark.
authors.forename: M M
authors.initials: MM
authors.lastname: Jensen
authors.affiliation: Interdisciplinary Nanoscience Center, Aarhus University, Aarhus, Denmark.
authors.forename: M
authors.initials: M
authors.lastname: Dong
authors.affiliation: Department of Chemistry, Aarhus University, Aarhus, Denmark; Interdisciplinary Nanoscience Center, Aarhus University, Aarhus, Denmark.
authors.forename: M
authors.initials: M
authors.lastname: Glasius
authors.affiliation: New Product Research, GlaxoSmithKline Consumer Healthcare, Research Triangle Park, NC, 27709, USA.
authors.forename: M J
authors.initials: MJ
authors.lastname: Clarke
authors.affiliation: Department of Engineering, Aarhus University, Aarhus, Denmark. Electronic address: guo@eng.au.dk.
authors.forename: Z
authors.initials: Z
authors.lastname: Guo
mesh_terms: D000215:Acylation; D002152:Calorimetry, Differential Scanning; D005227:Fatty Acids / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D008958:Models, Molecular; D020011:Protective Agents / Q000138:chemical synthesis / Q000737:chemistry*; D012867:Skin / Q000737:chemistry / Q000187:drug effects; D017550:Spectroscopy, Fourier Transform Infrared; D013227:Steam / Q000032:analysis
chemical_list: D005227:Fatty Acids; D020011:Protective Agents; D013227:Steam
keywords: Langmuir isotherm; O-acylated-ω-hydroxy fatty acid; Orthorhombic packing