Ascorbyl glucoside

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Ascorbyl glucoside
Ascorbyl glucoside.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 603-337-7
KEGG
PubChem CID
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 (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. [1] Ascorbyl glucosides such as AA-2G, like many other derivatives of the ascorbic acid, show antiscorbutic effects. [2] It is also sometimes used in skin whitening products. [3]

Ascorbyl glucoside is synthesized through a glycosylation process catalyzed by glycosyltransferase-class enzymes. [3]

See also

References

  1. ↑ Pullar, Juliet M.; Carr, Anitra C.; Vissers, Margreet C. M. (2017-08-12). "The Roles of Vitamin C in Skin Health". Nutrients. 9 (8): 866. doi: 10.3390/nu9080866 . ISSN   2072-6643. PMC   5579659 . PMID   28805671.
  2. ↑ Yamamoto, I.; Suga, S.; Mitoh, Y.; Tanaka, M.; Muto, N. (November 1990). "Antiscorbutic activity of L-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs". Journal of Pharmacobio-Dynamics. 13 (11): 688–695. doi: 10.1248/bpb1978.13.688 . ISSN   0386-846X. PMID   2093127.
  3. 1 2 "Current research situation and development prospect of ascorbyl glucoside--《Chinese Journal of Bioprocess Engineering》2008年04期". en.cnki.com.cn. Retrieved 2021-10-21.
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