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4-Nitrophenyl aD-glucopyranoside

Alias: 3767-28-0; 4-nitrophenyl-alpha-D-glucopyranoside; 4-Nitrophenyl alpha-D-glucopyranoside; 4-Nitrophenyl a-D-glucopyranoside; 4-Nitrophenyl alpha-glucoside; pNPalphaGlu; a-D-Glucopyranoside, 4-nitrophenyl; p-Nitrophenyl alpha-D-glucopyranoside;
Cat No.:V73779 Purity: =99.86%
4-Nitrophenyl aD-glucopyranoside is a chromogenic substrate for α-glucosidase.
4-Nitrophenyl aD-glucopyranoside
4-Nitrophenyl aD-glucopyranoside Chemical Structure CAS No.: 3767-28-0
Product category: Glutathione Peroxidase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
Other Sizes
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Purity & Quality Control Documentation

Purity: =99.86%

Product Description
4-Nitrophenyl aD-glucopyranoside is a chromogenic substrate for α-glucosidase. 4-Nitrophenyl aD-glucopyranoside may be utilized to measure alpha-glucosidase activity.
Biological Activity I Assay Protocols (From Reference)
Targets
α-glucosidase
ln Vitro
P-nitrophenol is released by 4-Nitrophenyl aD-glucopyranoside by enzymatic cleavage. By using colorimetric detection at 405 nm, p-nitrophenol can be measured[2].
Enzyme Assay
p-Nitrophenyl alpha-D-glucopyranoside has been shown to be a substrate for the glucansucrases of various strains of Leuconostoc mesenteroides and Streptococcus mutans. The products from a digest of p-nitrophenyl alpha-D-glucopyranoside with L. mesenteroides B-512F dextransucrase were found to include dextran, a series of p-nitrophenyl isomaltodextrin glycosides, and p-nitrophenyl nigeroside. The kinetics of the reaction were non-Michaelis-Menten, possibly because p-nitrophenyl alpha-D-glucopyranoside has a dual role in the reaction as both a D-glucosyl donor and acceptor [2].
References

[1]. Inhibitory mechanism of morin on α-glucosidase and its anti-glycation properties. Food Funct. 2016 Sep 14;7(9):3953-63.

[2]. p-Nitrophenyl alpha-D-glucopyranoside, a new substrate for glucansucrases. Carbohydr Res. 1983 Dec 23;124(2):287-99.

Additional Infomation
4-nitrophenyl alpha-D-glucoside is an alpha-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group. It has a role as a chromogenic compound. It is a monosaccharide derivative, an alpha-D-glucoside and a C-nitro compound. It is functionally related to a 4-nitrophenol.
It is important to investigate the inhibition of α-glucosidase due to its correlation with type 2 diabetes. Morin was found to exert significant inhibition activity on α-glucosidase in a reversible mixed-type manner with an IC50 value of (4.48 ± 0.04) μM. Analyses of fluorescence and circular dichroism spectra indicated that the formation of the morin-α-glucosidase complex was driven mainly by hydrophobic forces and hydrogen bonding, and caused the conformational changes of α-glucosidase. The phase diagrams of fluorescence showed that the conformational change process was monophasic without intermediates. Molecular docking indicated that morin mainly interacted with amino acid residues located close to the active site of α-glucosidase, which may move to cover the active pocket to reduce the binding of the substrate and then inhibit the catalytic activity. Morin was also found to exhibit inhibition in the generation of advanced glycation end products which was related to the long term complications of diabetes.[1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H15NO8
Molecular Weight
301.25
Exact Mass
301.079
Elemental Analysis
C, 47.84; H, 5.02; N, 4.65; O, 42.49
CAS #
3767-28-0
PubChem CID
92969
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
582.2±50.0 °C at 760 mmHg
Melting Point
210-216ºC
Flash Point
305.9±30.1 °C
Vapour Pressure
0.0±1.7 mmHg at 25°C
Index of Refraction
1.648
LogP
-0.55
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
354
Defined Atom Stereocenter Count
5
SMILES
C1=CC(=CC=C1[N+](=O)[O-])O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChi Key
IFBHRQDFSNCLOZ-ZIQFBCGOSA-N
InChi Code
InChI=1S/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-3-1-6(2-4-7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11-,12+/m1/s1
Chemical Name
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4,5-triol
Synonyms
3767-28-0; 4-nitrophenyl-alpha-D-glucopyranoside; 4-Nitrophenyl alpha-D-glucopyranoside; 4-Nitrophenyl a-D-glucopyranoside; 4-Nitrophenyl alpha-glucoside; pNPalphaGlu; a-D-Glucopyranoside, 4-nitrophenyl; p-Nitrophenyl alpha-D-glucopyranoside;
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

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)
DMSO: 50 mg/mL (165.98 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (8.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (8.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3195 mL 16.5975 mL 33.1950 mL
5 mM 0.6639 mL 3.3195 mL 6.6390 mL
10 mM 0.3320 mL 1.6598 mL 3.3195 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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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