Synthesis and characterization of O-acylated-ω-hydroxy fatty acids as skin-protecting barrier lipids
| Autor: | Anthony V. Rawlings, S.E. Dahlgaard, Mads Mørk Jensen, Bianca Pérez, Zheng Guo, Pallav A. Bulsara, Mingdong Dong, M.J. Clarke, Marianne Glasius |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Models
Molecular Acylation Protective Agents 01 natural sciences Biomaterials 030207 dermatology & venereal diseases 03 medical and health sciences chemistry.chemical_compound symbols.namesake 0302 clinical medicine Colloid and Surface Chemistry Differential scanning calorimetry Spectroscopy Fourier Transform Infrared 0103 physical sciences Stratum corneum medicine Humans Organic chemistry Fourier transform infrared spectroscopy Skin chemistry.chemical_classification Calorimetry Differential Scanning 010304 chemical physics Fatty Acids technology industry and agriculture Langmuir adsorption model Decanoic acid Surfaces Coatings and Films Electronic Optical and Magnetic Materials Steam Hydrocarbon medicine.anatomical_structure chemistry Melting point symbols lipids (amino acids peptides and proteins) Orthorhombic crystal system |
| Zdroj: | Pérez, B, Dahlgaard, S E, Bulsara, P, Jensen, M M, Dong, MD, Glasius, M, Clarke, M J & Guo, Z 2017, ' Synthesis and characterization of O-acylated-ω-hydroxy fatty acids as skin-protecting barrier lipids ', Journal of Colloid and Interface Science, vol. 490, pp. 137-146 . https://doi.org/10.1016/j.jcis.2016.11.031 |
| DOI: | 10.1016/j.jcis.2016.11.031 |
| Popis: | 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 (P0.001) which demonstrates the potential of these ingredients as occlusive technologies to combat skin barrier diseases. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|