2-o-(.beta.-d-glucopyranosyl) ascorbic acid, process for its...

C - Chemistry – Metallurgy – 07 – H

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C07H 17/04 (2006.01) A23L 1/30 (2006.01) A23L 1/302 (2006.01) A61K 8/60 (2006.01) A61K 31/7048 (2006.01) A61P 17/16 (2006.01) A61Q 17/00 (2006.01) A61Q 19/00 (2006.01) A61Q 19/02 (2006.01) C07H 1/08 (2006.01) C12P 19/60 (2006.01)

Patent

CA 2472114

The present invention provides a novel ascorbic acid derivative as a provitamin C with improved stability in the body and prolonged life in the body compared to conventionally known 2-O-(.alpha.-D-glucopyranosyl)ascorbic acid. The composition comprising the novel compound 2-O-(.beta.-D- glucopyranosyl)ascorbic acid has been extracted from plants such as from Ningxia Lycium barbarum L. and/or Lycium chinense Mill. The compositions comprising 2-O-(.beta.-D-glucopyranosyl)ascorbic acid may be enzymatically synthesized using .beta.-D-glucosyltransferase. Pure 2-O-(.beta.-D- glucopyranosyl)ascorbic acid may be produced from such compositions. Alternatively, 2-O-(.beta.-D-glucopyranosyl)ascorbic acid may be produced by chemical synthesis. The 2-O-(.beta.-D-glucopyranosyl)ascorbic acid results in higher stability and a prolonged life of vitamin C when ingested in the body compared to the corresponding .alpha.-D-glucopyranosyl derivative, and is therefore highly suitable as a provitamin C to be used in cosmetics and foods.

L'invention concerne un nouveau dérivé d'acide ascorbique en tant que provitamine C à stabilité améliorée et à durée de vie prolongée dans le corps par rapport à l'acide 2-O-(.alpha.-D-glucopyranosyl) ascorbique classique. La composition comprenant le nouveau composé d'acide 2-O-(.beta.-D-glucopyranosyl) ascorbique a été extrait de plantes notamment du Ningxia <i>Lycium barbarum</i> L. et/ou du <i>Lycium chinense</i> Mill. Les compositions comprenant l'acide 2-O-(.beta.-D-glucopyranosyl) ascorbique peuvent être synthétisées de façon enzymatique au moyen de .beta.-D-glucosyltransférase. De l'acide 2-O-(.beta.-D-glucopyranosyl) ascorbique pur peut être produit à partir de telles compositions. Dans un autre mode de réalisation, cet acide ascorbique peut être produit par synthèse chimique et entraîne une meilleure stabilité et une vie prolongée de la vitamine C lorsqu'il est ingéré dans le corps par rapport au dérivé .beta.-D-glucopyranosyl correspondant, c'est pourquoi il est très approprié de l'utiliser dans des produits cosmétiques et des aliments en tant que provitamine C.

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