2816-24-2

Basic information

• Product Name: 2-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE
• Synonyms: 2-NITROPHENYL BETA-D-GLUCOPYRANOSIDE, 98+%;2-Nitrophenyl β-D-glucopyranoside, 98+%;o-Nitrophenyl-β-D-glucopyranoside;2-Nitrophenyl ^b-D-glucopyranoside, 98+%;beta-D-Glucopyranoside, 2-nitrophenyl (9ci);Einecs 220-568-5;Glucopyranoside, o-nitrophenyl, beta-D- (8ci);Nsc 1947
• CAS NO: 2816-24-2
• Molecular Formula: C₁₂H₁₅NO₈
• Molecular Weight: 301.25
• EINECS: 220-568-5
• Product Categories: Substrates;Glucosidase, beta-;Enzyme Substrates;Substrates by Enzyme;Glucoside;Activity;Chromogenic;ChromogenicSubstrates;substrate
• Mol File: 2816-24-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 141-142℃
• Boiling Point: 572.4 °C at 760 mmHg
• Flash Point: 300 °C
• Appearance: light yellow/powder
• Density: 1.599 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.69±0.70(Predicted)
• Water Solubility: Soluble in water
• BRN: 92206
• CAS DataBase Reference: 2-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE(2816-24-2)
• EPA Substance Registry System: 2-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE(2816-24-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 2816-24-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

2-Nitrophenyl b-D-Glucopyranoside is used in preparation of phenol glycosides and their use in treatment of urolithiasis.

InChI:InChI=1/C12H15NO8/c14-5-8-9(15)10(16)11(17)12(21-8)20-7-4-2-1-3-6(7)13(18)19/h1-4,8-12,14-17H,5H2/t8-,9-,10+,11-,12+/m1/s1

Upstream product

• 14581-85-2 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 3053-17-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 24624-80-4 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(2-nitrophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 572-10-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride 
• 25878-60-8 D-galactose pentaacetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 88-75-5 2-hydroxynitrobenzene 
• 2280-44-6 D-Glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 

Downstream Products

• 21495-33-0 O¹-(2-nitro-phenyl)-β-D-galactopyranuronic acid 
• 497-76-7 arbutin 
• 10257-28-0 D-Galactose 
• 2595-07-5 allyl β-D-galactopyranoside 
• 3757-90-2 2-Acetamido-2-deoxy-6-O-(β-D-galactopyranosyl)-D-glucose 
• 114102-89-5 o-nitrophenyl 6-O-trityl-β-D-galactopyranoside 
• 4307-58-8 N-acetyl-D-lactosamine 
• 3646-73-9 α-D-galactopyranose 
• 7296-64-2 β-D-galactopyranoside 
• 139639-82-0 o-nitrophenyl β-D-galactopyranosyl<1->3>-β-D-galactopyranoside 
• 139639-81-9 o-nitrophenyl β-D-galactopyranosyl<1->6>-β-D-galactopyranoside 
• 530-26-7 D-Mannose 
• 31025-53-3 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 144683-66-9 (2S,3R,4S,5R,6R)-2-((3R,4R,5R,6S)-4,5-Dihydroxy-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Relevant articles and documents

Scope of the DMC mediated glycosylation of unprotected sugars with phenols in aqueous solution

Activation of reducing sugars in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and triethylamine in the presence of para-nitrophenol allows direct stereoselective conversion to the corresponding 1,2-Trans para-nitrophenyl glycosides without the need for any protecting groups. The reaction is applicable to sulfated and phosphorylated sugars, but not to ketoses or uronic acids or their derivatives. When applied to other phenols the product yield was found to depend on the pKa of the added phenol, and the process was less widely applicable to 2-Acetamido sugars. For 2-Acetamido substrates an alternative procedure in which the glycosyl oxazoline was pre-formed, the reaction mixture freeze-dried, and the crude product then reacted with an added phenol in a polar aprotic solvent system with microwave irradiation proved to be a useful simplification.

PHENOL GLYCOSIDES AND THEIR USE IN THE TREATMENT OF UROLITHIASIS

The present invention relates to novel derivatives of polyphenol glycoside or polyalcohols of formula (1), wherein R1, R2, R3 is selected from the group consisting of H, OH, C(O)R4, C(0) OR4, 0 (Gly H3)n, wherein n = 0 1, 2, 3, and R4 is selected from the group consisting of H, alkyl, and Gly is a mono- or disaccharide residue. The present invention also relates to novel derivatives of glycoside polyphenols or polyalcohols, as pharmaceutical composition comprising a novel polyphenol glycoside or polyalcohols and the use of novel polyphenol glycoside or polyalcohols for the treatment of urolithiasis.

Preparative Bioorganic Chemistry, XVI. Synthesis of 3,4'-Dihydroxypropiophenone 3-&β-D-Glucopyranoside, a Constituent of Betula platyphylla var. japonica, by Enzymatic Transglucosylation

3,4'-Dihydroxypropiophenone 3-β-D-glucopyranoside (1a) has been synthesized, without having recourse to any protective group technology, by transglucosylation catalyzed by lactase from Kluyveromyces lactis. Key words: Antifeedant; Betula platyphylla; β-D-glucopyranoside; lactase; transglucosylation.