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Synthesis of 2‐ N ‐oleoylamino‐octadecane‐1,3‐diol: a new ceramide highly effective for the treatment of skin and hair
Author(s) -
PHILIPPE M.,
GARSON J.C.,
GILARD P.,
HOCQUAUX M.,
HUSSLER G.,
LEROY F.,
MAHIEU C.,
SEMERIA D.,
VANLERBERGHE G.
Publication year - 1995
Publication title -
international journal of cosmetic science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.532
H-Index - 62
eISSN - 1468-2494
pISSN - 0142-5463
DOI - 10.1111/j.1467-2494.1995.tb00116.x
Subject(s) - ceramide , chemistry , octadecane , diastereomer , diol , moiety , oleic acid , stereochemistry , chromatography , organic chemistry , biochemistry , apoptosis
Synopsis 2‐ N ‐Oleoylamino‐octadecane‐1,3‐diol is a new synthetic ceramide. The process enables a four‐step preparation of 2‐amino‐octadecane‐1,3‐diol (D,L‐ erythro/threo ) and a five‐step synthesis of 2‐ N ‐oleoylamino‐octadecane‐1,3‐diol (D,L ‐erythro/threo ). The latter compound is related to ceramide 2 according to the classification of Downing. This route of synthesis is rapid, reproducible and uses low‐cost starting materials. The new ceramide was analysed as follows: 1 H, 13 C, 15 N NMR spectra afforded an unambiguous characterization of the structure; additionally, these three methods identified the threo and erythro isomers. 1 H and 13 C NMR permitted the measurement of the threo/erythro ratio (26.6/73.4 and 25.5/74.5, respectively). Chemical ionization mass spectrometry confirmed the expected mass of the pseudo‐molecular ion ( m/z = 566.5: [M + H] + ) as well as the presence of different chain lengths other than the oleic moiety due to the fatty acid composition of the technical grade oleic acid used for the synthesis. Capillary gas chromatography measured the threo/erythro ratio (23.5/76.5) which agrees with the 1 H and 13 C NMR data. Moreover, this method afforded the relative distribution of the different N ‐acylated chains. The properties of the new synthetic ceramide for the treatment of skin and hair were mainly assessed by two in vitro methods. The first measured the flux of water through lipid‐extracted stratum corneum. The described ceramide showed high efficacy in decreasing water loss. The second recorded the friction coefficient of different types of hair: virgin, permanent‐waved, and bleached. Treatment by the ceramide led to a strong decrease in this coefficient. This was particularly observed on unrinsed hair. These findings suggest two potential fields of application and beneficial contribution for the new ceramide: repairing the barrier to transepidermal water loss, and improving the surface properties of hair. Synthèse du 2‐ N ‐oleoylamino‐octadécane‐1,3‐diol: nouveau céramide à haut potentiel dans le soin de la peau et du cheveu.