Ascorbyl glucoside

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
CAS Number	129499-78-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81685;
ChEMBL	ChEMBL2011961;
ChemSpider	18678797;
DrugBank	DB11335;
EC Number	603-337-7;
KEGG	C18339;
PubChem CID	54693473;
UNII	2V52R0NHXW;
	InChI 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;
	SMILES 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
Chemical formula	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).
	Infobox references

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]

References

↑ 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. PMID 28805671.
↑ 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.
↑ ^3.0 ^3.1 "Current research situation and development prospect of ascorbyl glucoside--《Chinese Journal of Bioprocess Engineering》2008年04期". https://en.cnki.com.cn/Article_en/CJFDTotal-SWJG200804002.htm.

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[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. 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.

[:0-3] 3.0 ^3.1 "Current research situation and development prospect of ascorbyl glucoside--《Chinese Journal of Bioprocess Engineering》2008年04期". https://en.cnki.com.cn/Article_en/CJFDTotal-SWJG200804002.htm.

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Ascorbyl glucoside

Topic: Chemistry

See also

References