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SMB00390

Sigma-Aldrich

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

≥98% (HPLC)

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Synonym(s):
Ascorbyl Glucoside, Ascorbic acid 2-glucoside
Empirical Formula (Hill Notation):
C12H18O11
CAS Number:
Molecular Weight:
338.26
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.79

Quality Level

assay

≥98% (HPLC)

form

powder

technique(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

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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.
2-O-a-D-Glucopyranosyl-L-ascorbic acid is a form of vitamin C combined with glucose.

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.

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.
2-O-a-D-Glucopyranosyl-L-ascorbic acid can function as an antioxidant, an antineoplastic, and a tyrosine kinase inhibitor.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Flow Injection Analysis of Ascorbyl Glucoside in Cosmetics by a Disposable Printed-Circuit Board Waste Modified Electrode.
Shih Y and Zen JM
J. Chin. Chem. Soc., 53(4), 857-862 (2006)
Combining high-performance liquid chromatography with on-line microdialysis sampling for the simultaneous determination of ascorbyl glucoside, kojic acid, and niacinamide in bleaching cosmetics.
Lin CH et al
Analytica Chimica Acta, 581(1), 102-107 (2007)
Li Xiao et al.
Human cell, 33(4), 1056-1067 (2020-08-08)
Cutaneous wound healing delay, collagen synthesis decline and wrinkle formation are the common features of skin aging. The aim of this study is to investigate repressive effects of Colla Corii Asini (CCA) (a traditional Chinese medicine which has been used
Advances in Carbohydrate Chemistry and Biochemistry, 68 (2012)
Corneal Tissue Engineering: An In Vitro Model of the Stromal-nerve Interactions of the Human Cornea
Sharif R, et al.
Journal of Visualized Experiments, 68(131) (2018)

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