Synthesis of Pro-Xylane: a new biologically active C-glycoside in aqueous media.
The scope and limitation of Lubineau's reaction were evaluated for the synthesis of C-glycosides (compounds 1-13). Further transformation of side chain carbonyl was also achieved (compounds 16-23). Optimization of these two steps was investigated in xylose case. Some of the compounds were shown to stimulate sulfated glycosaminoglycans (GAGs) synthesis. Compound 20 (called Pro-Xylane) was identified as the best activator of GAGs biosynthesis. Pro-Xylane was developed using environmentally friendly conditions relevant to 'Green-Chemistry' principles and launched on the market in September 2006. This compound is the first example of 'Green' chemical used in cosmetic.
Cavezza
Alexandre
A
L'Oréal Recherche, Personal Care Chemistry, 93601 Aulnay sous Bois, Cedex, France.
Boulle
Christophe
C
Guéguiniat
Amélie
A
Pichaud
Patrick
P
Trouille
Simon
S
Ricard
Louis
L
Dalko-Csiba
Maria
M
D000438:Alcohols / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D006025:Glycosaminoglycans / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006801:Humans; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D011509:Proteoglycans / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D014867:Water / Q000737:chemistry; D014994:Xylose / Q000737:chemistry
D000438:Alcohols; C531898:C-xylopyranoside-2-hydroxypropane; D006025:Glycosaminoglycans; D006027:Glycosides; D007659:Ketones; D011509:Proteoglycans; D012997:Solvents; D014867:Water; D002244:Carbon; D014994:Xylose