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Ascorbyl glucoside

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Ascorbyl glucoside is a widely used ingredient in cosmetics, personal care, and skincare formulations. Depending on its function, it may serve as a moisturizer, preservative, emulsifier, or active ingredient to enhance the overall effectiveness and performance of a product.

Ascorbyl glucoside (Wikipedia)

Ascorbyl glucoside (AA-2G) is an ascorbic acid derivative that contains at least one glycosyl group. Ascorbyl glucoside is commonly used in cosmetic products to administer vitamin C topically. Ascorbyl glucoside exhibits superior stability and penetration ability compared to ascorbyl phosphate salts, but the rate of its in vivo conversion to ascorbic acid is not known. Ascorbyl glucosides such as AA-2G, like many other derivatives of the ascorbic acid, show antiscorbutic effects. It is also sometimes used in skin whitening products.

Ascorbyl glucoside
Names
IUPAC name
(2R)-2-[(1S)-1,2-Dihydroxyethyl]-3-hydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-furan-5-one
Other names
Ascorbic acid 2-O-glucoside; 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid; AA-2G; L-Ascorbic acid 2-O-alpha-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.114.373 Edit this at Wikidata
EC Number
  • 603-337-7
KEGG
UNII
  • InChI=1S/C12H18O11/c13-1-3(15)9-8(19)10(11(20)22-9)23-12-7(18)6(17)5(16)4(2-14)21-12/h3-7,9,12-19H,1-2H2/t3-,4+,5+,6-,7+,9+,12+/m0/s1
    Key: MLSJBGYKDYSOAE-DCWMUDTNSA-N
  • C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC2=C([C@H](OC2=O)[C@H](CO)O)O)O)O)O)O
Properties
C12H18O11
Molar mass 338.265 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ascorbyl glucoside is synthesized through a glycosylation process catalyzed by glycosyltransferase-class enzymes.

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