An L-ascorbic acid derivative with antioxidant and radioprotective activities
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2-O-α-D-Glucopyranosyl-L-ascorbic Acid

Item No. 31402

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
129499-78-1
Synonyms
  • AA-2G
  • Asc2G
  • Ascorbic Acid 2-glucoside
Molecular Formula
C12H18O11
Formula Weight
338.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/mlPBS (pH 7.2): 1 mg/ml
λmax
234 nm
SMILES
OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1OC2=C(O)[C@]([C@H](CO)O)([H])OC2=O
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    5 g

    $107

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    10 g

    $203

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    25 g

    $477

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    50 g

    $794

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    Product Description

    2-O-α-D-Glucopyranosyl-L-ascorbic acid (AA-2G) is a glucosylated derivative of L-ascorbic acid (Item No. 14656) that has antioxidant and radioprotective activities.1,2,3 It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (EC50 = 61 μM in 60% ethanol).1 AA-2G (5 mM) inhibits γ-radiation-induced cell death in CHO-10B2 and radiosensitive xrs5 cells, as well as UVC- or broadband UVB-induced cell death in CHO-10B2 and UV-sensitive UV135 cells.2 It is hydrolyzed to ascorbic acid by α-glucosidase and increases serum levels of ascorbic acid in rats and guinea pigs when administered orally at doses of 19.2 and 96 mg/animal, respectively.3 AA-2G (19.2 mg/animal per day) reverses weight loss and inhibits subcutaneous hemorrhage in guinea pigs fed a vitamin C-deficient diet.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fujinami, Y., Tai, A., and Yamamoto, I. Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G. Chem. Pharm. Bull. (Tokyo) 49(5):, 642-644 (2001).

    2. Maeda, J., Allum, A.J., Mussallem, J.T., et al. Ascorbic acid 2-glucoside pretreatment protects cells from ionizing radiation, UVC, and short wavelength of UVB. Genes (Basel) 11(3), 238 (2020).

    3. Yamamoto, I., Suga, S., Mitoh, Y., et al. Antiscorbutic activity of ʟ-ascorbic acid 2-glucoside and its availability as a vitamin C supplement in normal rats and guinea pigs. J. Pharmacobiodyn 13(11), 688-695 (1990).