2-O-alpha-D-Glucopyranosyl-L-ascorbic acid
[CAS# 129499-78-1]

Identification

• Classification: Analytical chemistry >> Analytical reagent >> Ion chromatography reagent
• Name: 2-O-alpha-D-Glucopyranosyl-L-ascorbic acid
• Synonyms: AA 2G; Ascofresh
• Molecular Formula: C₁₂H₁₈O₁₁
• Molecular Weight: 338.26
• CAS Registry Number: 129499-78-1
• EC Number: 425-980-0
• 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

• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.670, Calc.^*
• Boiling Point: 785.6±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 296.5±26.4 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

2-O-a-D-Glucopyranosyl-L-ascorbic acid, commonly known as AA-2G, is a stable derivative of ascorbic acid (vitamin C). It was discovered through chemical modification of ascorbic acid to enhance its stability and bioavailability in various applications. The synthesis of AA-2G involves the enzymatic glycosylation of ascorbic acid with glucose, resulting in the formation of a glycosidic bond between the two molecules. This process increases the compound's stability, making it more effective at resisting degradation and oxidation than ascorbic acid alone.

Ascorbic acid is known for its ability to scavenge free radicals and protect the skin from oxidative stress, which can lead to premature aging and damage. However, pure ascorbic acid is prone to oxidation and instability when exposed to air, light, and heat, limiting its effectiveness in skin care formulations. AA-2G overcomes this limitation by providing stable, water-soluble vitamin C that can be added to a variety of skin care products, including serums, creams, and lotions. AA-2G is used in anti-aging treatments and formulations targeting fine lines, wrinkles and age spots. By neutralizing free radicals and stimulating collagen production, AA-2G helps improve skin texture, reduce the appearance of wrinkles and promote a more even skin tone. It also helps protect skin from environmental damage caused by UV radiation, pollution and other external aggressors. AA-2G is a popular ingredient in skin whitening and whitening products because of its ability to inhibit the activity of tyrosinase, an enzyme involved in melanin synthesis, preventing the formation of excess melanin in the skin. AA-2G is incorporated into hair care formulas such as shampoos, conditioners and hair masks because of its antioxidant properties and ability to protect hair from damage caused by UV radiation, pollution and styling tools. AA-2G is available as an oral supplement and may be consumed as a dietary supplement. As a source of vitamin C, AA-2G provides antioxidant support and immune system benefits, helping to strengthen the body's natural defenses against infection, disease, and environmental toxins.

References

2025. Production of 2-O-α-D-glucopyranosyl-L-ascorbic acid using sucrose phosphorylase. International Journal of Biological Macromolecules, 286, 138213.
DOI: 10.1016/j.ijbiomac.2024.138213

2024. Persulfated Ascorbic Acid Glycoside for Skin Care. Molecules, 29(19), 4604.
DOI: 10.3390/molecules29194604

2023. Promoter engineering for sucrose phosphorylase in 2-O-α-D-glucopyranosyl-L-ascorbic acid synthesis. Enzyme and Microbial Technology, 169, 110267.
DOI: 10.1016/j.enzmictec.2023.110267