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SMB00390 Sigma-Aldrich

2-O-a-D-Glucopyranosyl-L-ascorbic Acid

≥98% (HPLC)

Synonym: Ascorbic acid 2-glucoside, Ascorbyl Glucoside

  • CAS Number 129499-78-1

  • Empirical Formula (Hill Notation) C12H18O11

  • Molecular Weight 338.26

  •  MDL number MFCD23701380

  •  PubChem Substance ID 329824985

  •  NACRES NA.79

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Properties

Related Categories Antioxidant, Biochemicals and Reagents, Carbohydrates, Carbohydrates A to Z, Carbohydrates G,
Quality Level   200
assay   ≥98% (HPLC)
form   powder
application(s)   HPLC: suitable
  tissue processing: suitable
color   white to off-white
mp   158-163 °C
storage temp.   2-8°C
SMILES string   OC([C@]([C@@H](O)CO)([H])O1)=C(C1=O)O[C@H]([C@@H]([C@@H](O)[C@@H]2O)O)O[C@@H]2CO
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
InChI key   MLSJBGYKDYSOAE-DCWMUDTNSA-N

Description

General description

2-O-a-D-glucopyranosyl-L-ascorbic acid, generally known as ascorbyl glucoside, is a relatively novel compound and is a stable vitamin C derivative. Over a long period of time, it gradually is converted into ascorbic acid.

2-O-a-D-Glucopyranosyl-L-ascorbic Acid is derived from L-ascorbic acid and α-glucosyl donor saccharide, in the presence of α-isomaltosylglucosaccharide producing enzyme.

Application

2-O-a-D-Glucopyranosyl-L-ascorbic acid has been used to develop an in vitro 3D model of the stromal-nerve interactions of the human cornea.

Packaging

1 g in poly bottle

Biochem/physiol Actions

2-O-a-D-glucopyranosyl-L-ascorbic acid or ascorbyl glucoside functions as a skin whitener and radical scavenger in cosmetics. It is responsible for the bleaching action of bleaching cosmetics. This compound is activated in a manner identical to that of vitamin C. The enzyme present in the epidermal basal membrane, ascorbyl phosphatase, slowly converts 2-O-a-D-glucopyranosyl-L-ascorbic acid into vitamin C, thereby maintaining a high vitamin C level in skin throughout the day.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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