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SMB00390

Sigma-Aldrich

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

≥98% (HPLC)

Sinonimo/i:

Ascorbyl Glucoside, Ascorbic acid 2-glucoside

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About This Item

Formula empirica (notazione di Hill):
C12H18O11
Numero CAS:
Peso molecolare:
338.26
Numero MDL:
Codice UNSPSC:
12352205
ID PubChem:
NACRES:
NA.79

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

powder

tecniche

HPLC: suitable
tissue processing: suitable

Colore

white to off-white

Punto di fusione

158-163 °C

Temperatura di conservazione

2-8°C

Stringa SMILE

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
MLSJBGYKDYSOAE-DCWMUDTNSA-N

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Descrizione generale

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.

Applicazioni

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.

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable


Certificati d'analisi (COA)

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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)
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.
Antioxidants (Basel, Switzerland), 10(1) (2021-01-13)
Ultraviolet-A (UVA) irradiation induces harmful effects on skin cells and accelerates skin aging through oxidative stress. In this study, the effects of a hydrogen-generating silica material named ULH-002 against UVA injuries in human cells and 3D skin equivalents were investigated.

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