2-O-(β-D-glucopyranosyl) ascorbic acid, process for its production, and foods and cosmetics containing compositions comprising it
View Patent ↗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-(α-D-glucopyranosyl)ascorbic acid. The composition comprising the novel compound 2-O-(β-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-(β-D-glucopyranosyl)ascorbic acid may be enzymatically synthesized using β-D-glucosyltransferase. Pure 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced from such compositions. Alternatively, 2-O-(β-D-glucopyranosyl)ascorbic acid may be produced by chemical synthesis. The 2-O-(β-D-glucopyranosyl)ascorbic acid results in higher stability and a prolonged life of vitamin C when ingested in the body compared to the corresponding α-D-glucopyranosyl derivative, and is therefore highly suitable as a provitamin C to be used in cosmetics and foods.
1. Isolated and/or purified 2-O-(β-D-Glucopyranosyl)ascorbic acid represented by the following formula (1):
or a biologically acceptable salt or ester thereof.
2. 2-O-(Tetra-O-acyl-β-D-glucopyranosyl)ascorbic acid represented by the following formula (2):
wherein each R in the formula independently represents a C 1-5 alkyl group.
3. The compound of claim 2 , wherein all of the R groups of formula (2) are methyl.
4. A method of producing 2-O-(β-D-glucopyranosyl)ascorbic acid comprising reacting ascorbic acid and a β-D-glucosyl compound in the presence of a β-D-glucosyltransferase that is a cellulase.
5. The method of claim 4 , wherein the cellulase is a cellulase from Trichoderma.
6. A provitamin C composition comprising 2-O-(β-D-glucopyranosyl)ascorbic acid in the amount of 0.1 to 30 weight percent, and a pharmaceutically, cosmetically, or dietarily acceptable component.
7. A provitamin C composition comprising 2-O-(β-D-glucopyranosyl)ascorbic acid and 6-O-(β-D-glucopyranosyl)ascorbic acid.
8. A pharmaceutical composition comprising the 2-O-(β-D-glucopyranosyl)ascorbic acid or a biologically acceptable salt or ester thereof of claim 1 , wherein said 2-O-(β-D-glucopyranosyl)ascorbic acid or biologically acceptable salt or ester thereof is present in the amount of 0.1 to 30 weight percent, and a pharmaceutically acceptable carrier.
9. A cosmetic composition comprising the 2-O-(β-D-glucopyranosyl)ascorbic acid or a biologically acceptable salt or ester thereof of claim 1 , and a cosmetically acceptable carrier.
10. The cosmetic composition of claim 9 , wherein said 2-O-(β-D-glucopyranosyl)ascorbic acid or biologically acceptable salt or ester thereof is present in the amount of 0.1 to 30 weight percent.
11. A method of producing 2-O-(β-D-glucopyranosyl)ascorbic acid comprising reacting ascorbic acid and a β-D-glucosyl compound in the presence of a β-D-glucosyltransferase, wherein the β-D-glucosyl compound is cellobiose.