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2-O-β-D-Glucopyranosyl-L-ascorbic acid

Cat No.:V30126 Purity: ≥98%
2-O-β-D-Glucopyranosyl-L-ascorbic acid (AA-2βG) is extracted from Lycium chinense and is a stable vitamin C analog with anti-tumor activity.
2-O-β-D-Glucopyranosyl-L-ascorbic acid
2-O-β-D-Glucopyranosyl-L-ascorbic acid Chemical Structure CAS No.: 562043-82-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2-O-β-D-Glucopyranosyl-L-ascorbic acid (AA-2βG) is extracted from Lycium chinense and is a stable vitamin C analog with anti-tumor activity.
2-O-beta-D-Glucopyranosyl-L-ascorbic acid (CAS#: 562043-82-7) is a stable, naturally derived ascorbic acid (vitamin C) analog, characterized by a glucose moiety linked at the 2-position. Also known as AA-2betaG, it is extracted from Lycium chinense. It has a molecular formula of C12H18O11 and a molecular weight of 338.26. The compound is a stable vitamin C analog with anti-tumor activity.
Biological Activity I Assay Protocols (From Reference)
Targets
2-O-beta-D-Glucopyranosyl-L-ascorbic acid targets the vitamin C signaling pathway and related cellular processes. As a stable ascorbic acid analog, it serves as a source of vitamin C activity with improved stability compared to ascorbic acid. Its anti-tumor activity suggests interactions with cellular pathways involved in cell proliferation and apoptosis. The compound may also act as an antioxidant, similar to vitamin C.
ln Vitro
In vitro, 2-O-beta-D-Glucopyranosyl-L-ascorbic acid (AA-2betaG) is a stable vitamin C analog with anti-tumor activity. Its stability compared to ascorbic acid makes it valuable for research applications. The compound's anti-tumor activity has been characterized in cell-based assays measuring cell proliferation and apoptosis. Its antioxidant properties can be assessed using standard antioxidant assays such as DPPH or ABTS radical scavenging assays.
ln Vivo
In vivo activity of 2-O-beta-D-Glucopyranosyl-L-ascorbic acid is inferred from its anti-tumor activity. As a stable vitamin C analog, it may have antioxidant and anti-tumor effects in vivo. However, detailed in vivo data for this compound are limited in the available literature. The compound is extracted from Lycium chinense and is used as a research tool for studying vitamin C biology and anti-tumor activity.
Enzyme Assay
The in vitro antioxidant assay for 2-O-beta-D-Glucopyranosyl-L-ascorbic acid involves measuring its free radical scavenging activity. The compound is dissolved in appropriate solvent and tested at varying concentrations (typically 0.1-1000 uM) in DPPH or ABTS radical scavenging assays. The decrease in absorbance at 517 nm (DPPH) or 734 nm (ABTS) is measured spectrophotometrically after incubation at room temperature for 30 minutes. The IC50 for radical scavenging is determined from dose-response curves. For anti-tumor studies, the compound's effects on cell proliferation and apoptosis are assessed in cancer cell lines.
Cell Assay
In vitro cellular assays for 2-O-beta-D-Glucopyranosyl-L-ascorbic acid are conducted using cancer cell lines to assess its anti-tumor activity. Cells are seeded in 96-well plates and treated with varying concentrations of the compound (typically 0.1-1000 uM) for 24-72 hours. Cell viability is assessed using MTT, CellTiter-Glo, or crystal violet staining assays. Apoptosis is evaluated using Annexin V-FITC/PI double staining or by measuring caspase-3/7 activity. Antioxidant effects in cells can be assessed by measuring reactive oxygen species (ROS) levels using fluorescent probes such as DCFH-DA. Gene expression changes related to apoptosis and antioxidant defense are analyzed by qPCR.
Animal Protocol
In vivo animal studies for 2-O-beta-D-Glucopyranosyl-L-ascorbic acid are not extensively documented. As a compound with anti-tumor activity, typical studies would involve xenograft models in immunodeficient mice bearing human tumor cell lines. The compound would be administered by oral gavage or intraperitoneal injection at doses determined from preliminary pharmacokinetic and tolerability studies. Tumor growth inhibition would be assessed, and standard toxicology parameters including body weight and clinical observations would be monitored.
ADME/Pharmacokinetics
Pharmacokinetic properties of 2-O-beta-D-Glucopyranosyl-L-ascorbic acid are characteristic of a glycosylated vitamin C analog. The compound has a molecular weight of 338.26 and a molecular formula of C12H18O11. It is freely soluble in water (879 g/L at 25degC) and has a density of 1.83 g/cm3. As a polar, water-soluble compound, it is expected to have good aqueous solubility. The glucose moiety may affect its transport and metabolism compared to ascorbic acid. Detailed ADME parameters are not extensively documented.
Toxicity/Toxicokinetics
The toxicological profile of 2-O-beta-D-Glucopyranosyl-L-ascorbic acid has not been extensively characterized. As a stable vitamin C analog derived from a natural source (Lycium chinense), it is expected to have low toxicity. The compound is for research use only and is not intended for human therapeutic use. Standard safety precautions should be followed when handling the compound in a laboratory setting. No specific LD50 values have been reported.
References

[1]. Selective suppression of cervical cancer Hela cells by 2-O-β-D-glucopyranosyl-L-ascorbic acid isolated from the fruit of Lycium barbarum L. Cell Biol Toxicol. 2011 Apr;27(2):107-21.

Additional Infomation
2-O-beta-D-Glucopyranosyl-L-ascorbic acid (CAS 562043-82-7) is a stable vitamin C analog with a glucose moiety at the 2-position. Also known as AA-2betaG, it is extracted from Lycium chinense and has anti-tumor activity. The compound is a research tool for studying vitamin C biology and anti-tumor activity. It is available for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H18O11
Molecular Weight
338.2647
Exact Mass
338.084
CAS #
562043-82-7
PubChem CID
54725703
Appearance
White to light yellow solid powder
LogP
-3.1
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
5
Heavy Atom Count
23
Complexity
478
Defined Atom Stereocenter Count
0
SMILES
O1[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])C([H])([H])O[H])O[H])O[H])O[H])OC1C(=O)O[C@]([H])([C@]([H])(C([H])([H])O[H])O[H])C=1O[H]
InChi Key
MLSJBGYKDYSOAE-UHFFFAOYSA-N
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
Chemical Name
2-(1,2-dihydroxyethyl)-3-hydroxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2H-furan-5-one
HS Tariff Code
2934.99.9001
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)
Solubility Data
Solubility (In Vitro)
H2O : ≥ 250 mg/mL (~739.08 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (295.63 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.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.
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