| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 5g |
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| Other Sizes |
| Targets |
2-O-α-D-Glucopyranosyl-L-ascorbic Acid does not have a direct biological target itself; rather, it functions as a stable prodrug of L-ascorbic acid (vitamin C). The compound is enzymatically hydrolyzed by α-glucosidases, which are present in various tissues and biological fluids, to release free ascorbic acid. The released ascorbic acid then exerts its biological effects, which include acting as a potent antioxidant by scavenging reactive oxygen species (ROS), regenerating other antioxidants such as vitamin E, and serving as a cofactor for various enzymes, including those involved in collagen synthesis, neurotransmitter production, and epigenetic regulation. By providing a stable and sustained release of ascorbic acid, this glucoside derivative enhances the bioavailability and efficacy of vitamin C in biological systems. Its antioxidant and radioprotective activities are attributed to the ascorbic acid released upon hydrolysis.
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| ln Vitro |
The primary in vitro activity of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid is its ability to act as a stable source of ascorbic acid. In cell culture, the compound is taken up by cells and hydrolyzed by intracellular α-glucosidases to release ascorbic acid, which then exerts its biological effects. Studies have shown that this compound exhibits anti-cancer effects, likely due to the cytotoxic effects of ascorbic acid at high concentrations, which can generate hydrogen peroxide and induce oxidative stress in cancer cells. It also demonstrates antioxidant and radioprotective activities by scavenging ROS and protecting cells from radiation-induced damage. The compound's physicochemical properties include a molecular formula of C₁₂H₁₈O₁₁ and a molecular weight of 338.26. It is highly soluble in water (up to 125 mg/mL).
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| ln Vivo |
In vivo, 2-O-α-D-Glucopyranosyl-L-ascorbic Acid serves as a stable and bioavailable source of vitamin C. After oral or parenteral administration, the compound is gradually hydrolyzed to release ascorbic acid, providing a sustained supply of the vitamin. This property makes it particularly useful for studies requiring prolonged antioxidant protection or for delivering high doses of vitamin C with reduced gastrointestinal irritation compared to free ascorbic acid. Its radioprotective effects have been demonstrated in animal models, where it helps to mitigate the damaging effects of ionizing radiation. The compound's ability to maintain stable ascorbic acid levels in vivo makes it a valuable tool for investigating the physiological and therapeutic roles of vitamin C.
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| Enzyme Assay |
In vitro biochemical assays for 2-O-α-D-Glucopyranosyl-L-ascorbic Acid are not typically performed to measure binding to a specific enzyme or receptor. Instead, assays are focused on measuring its stability, its hydrolysis to ascorbic acid, and its antioxidant activity. The compound's stability can be assessed by incubating it in various buffers and measuring its degradation over time using HPLC. Its hydrolysis by α-glucosidases can be measured by incubating the compound with the enzyme and quantifying the release of ascorbic acid. Antioxidant activity is commonly measured using assays such as DPPH radical scavenging, ABTS radical scavenging, or the ferric reducing antioxidant power (FRAP) assay. These assays provide a measure of the compound's capacity to neutralize free radicals.
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| Cell Assay |
In vitro cell-based assays for 2-O-α-D-Glucopyranosyl-L-ascorbic Acid are used to evaluate its effects on cell viability, oxidative stress, and radioprotection. Cells (e.g., cancer cell lines, fibroblasts, or neuronal cells) are treated with the compound, and the intracellular levels of ascorbic acid are measured to confirm its uptake and hydrolysis. The compound's antioxidant effects are assessed by exposing cells to oxidative stress (e.g., hydrogen peroxide or UV radiation) in the presence or absence of the compound and measuring cell viability, ROS levels, and markers of oxidative damage. Its anti-cancer effects are evaluated by measuring cell proliferation, apoptosis, and the generation of reactive oxygen species in cancer cell lines. These assays provide insights into the cellular mechanisms of action of this vitamin C prodrug.
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| Animal Protocol |
In vivo animal studies for 2-O-α-D-Glucopyranosyl-L-ascorbic Acid are typically conducted to evaluate its effects on oxidative stress, radioprotection, and cancer. In radioprotection studies, animals are exposed to ionizing radiation and treated with the compound, and endpoints such as survival, tissue damage, and oxidative stress markers are measured. In cancer studies, the compound's ability to inhibit tumor growth or enhance the efficacy of chemotherapy or radiotherapy is evaluated in xenograft models. The compound is typically administered orally or intraperitoneally, and its pharmacokinetics and tissue distribution are also assessed.
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| ADME/Pharmacokinetics |
The pharmacokinetic (PK) properties of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid are characterized by its stability and its gradual conversion to ascorbic acid. After oral administration, the compound is absorbed from the gastrointestinal tract and distributed to various tissues, where it is hydrolyzed by α-glucosidases to release ascorbic acid. This results in a sustained increase in plasma and tissue ascorbic acid levels compared to administration of free ascorbic acid. The compound is highly soluble in water (up to 125 mg/mL) and is stable as a powder at -20°C for up to three years. For in vivo administration, it can be dissolved in water or saline.
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| Toxicity/Toxicokinetics |
The toxicological profile of 2-O-α-D-Glucopyranosyl-L-ascorbic Acid is generally considered to be favorable, as it is a derivative of vitamin C, which has a well-established safety profile. The compound is non-toxic at concentrations typically used for research purposes. However, at very high doses, it may cause gastrointestinal disturbances, similar to those caused by high doses of ascorbic acid. For laboratory handling, standard safety precautions for research chemicals should be observed. The compound is intended for research use only and is not for human therapeutic or diagnostic use.
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| Additional Infomation |
L-Ascorbic acid-2-glucoside is a glycoside.
See also: ... View more ... 2-O-α-D-Glucopyranosyl-L-ascorbic Acid is a glucoside derivative of L-ascorbic acid, also known as ascorbic acid 2-glucoside (AA-2G). It has a molecular formula of C₁₂H₁₈O₁₁ and a molecular weight of 338.26. The compound is supplied as a white to off-white solid powder with a purity of ≥98%. It is highly soluble in water (up to 125 mg/mL). For research use, it is typically stored as a powder at -20°C for up to three years or in solution at -80°C for up to six months, protected from light. The compound is a valuable tool for studying the biology of ascorbic acid, its antioxidant and radioprotective effects, and its potential therapeutic applications, particularly in cancer and radioprotection. |
| Molecular Formula |
C12H18O11
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|---|---|
| Molecular Weight |
338.26472
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| Exact Mass |
338.084
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| CAS # |
129499-78-1
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| PubChem CID |
54693473
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| Appearance |
White to off-white solid powder
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| Density |
1.83±0.1 g/cm3
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| Boiling Point |
785.6±60.0 °C at 760 mmHg
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| Melting Point |
158-163℃
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| Flash Point |
296.5±26.4 °C
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| Vapour Pressure |
0.0±6.2 mmHg at 25°C
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| Index of Refraction |
1.670
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| LogP |
-2.57
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
11
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
23
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| Complexity |
478
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| Defined Atom Stereocenter Count |
7
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| SMILES |
C([C@@H]([C@@H]1C(=C(C(=O)O1)O[C@@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)O
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| InChi Key |
MLSJBGYKDYSOAE-DCWMUDTNSA-N
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| 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
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| Chemical Name |
(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-furan-5-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O : ~125 mg/mL (~369.54 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 50 mg/mL (147.82 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9563 mL | 14.7815 mL | 29.5631 mL | |
| 5 mM | 0.5913 mL | 2.9563 mL | 5.9126 mL | |
| 10 mM | 0.2956 mL | 1.4782 mL | 2.9563 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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