10238-28-5

Basic information

• Product Name: P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE
• Synonyms: PNP ALPHA-D-XYLOPYRANOSIDE;P-NITROPHENYL A-D-XYLOPYRANOSIDE;P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE;XYL1-ALPHA-PNP;XYL1-A-PNP;4-NITROPHENYL-ALPHA-D-XYLOPYRANOSIDE;P-Nitrophenyl-Alpha-D-XylopyanosideA.R.;4-Nitrophenyla-D-xylopyranoside
• CAS NO: 10238-28-5
• Molecular Formula: C11H13NO7
• Molecular Weight: 271.22
• EINECS: 233-572-7
• Product Categories: Substrates;13C & 2H Sugars;Carbohydrates & Derivatives;Activity;Chromogenic;ChromogenicSubstrates;Enzyme Substrates;Xyloside;Aromatics;substrate
• Mol File: 10238-28-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 170-172°C
• Boiling Point: 523.2 °C at 760 mmHg
• Flash Point: 270.2 °C
• Appearance: WHITE TO OFF-WHITE POWDER
• Density: 1.597 g/cm³
• Vapor Pressure: 8.94E-12mmHg at 25°C
• Refractive Index: 1.654
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.67±0.70(Predicted)
• CAS DataBase Reference: P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE(10238-28-5)
• EPA Substance Registry System: P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE(10238-28-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 10238-28-5(Hazardous Substances Data)

Usage

Description

P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE, also known as a chromogenic substrate for α-xylosidase, is a xyloside derivative where the anomeric hydroxy hydrogen of alpha-D-xylopyranose is replaced by a 4-nitrophenyl group. It is a white crystalline solid and is widely used in various applications due to its unique chemical properties.

Uses

1. Used in Enzyme Assays:
P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE is used as a chromogenic substrate for alpha-xylosidase, an enzyme that catalyzes the hydrolysis of xylo-oligosaccharides and xylo-polysaccharides. The substrate's ability to change color upon enzymatic action makes it a valuable tool for monitoring enzyme activity, studying enzyme kinetics, and detecting enzyme deficiencies in various research and diagnostic applications.
2. Used in Pharmaceutical Research:
In the pharmaceutical industry, P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its unique chemical structure allows for the development of novel therapeutic agents targeting specific biological pathways.
3. Used in Analytical Chemistry:
P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE is employed as a reference compound and a standard in analytical chemistry for the calibration of instruments and the development of new methods for the detection and quantification of xylo-oligosaccharides and xylo-polysaccharides.
4. Used in Food Industry:
In the food industry, P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE can be used as a component in the development of novel food additives or as a tool for the analysis of xylose-containing compounds in various food products.
5. Used in Environmental Science:
P-NITROPHENYL ALPHA-D-XYLOPYRANOSIDE can be utilized in environmental science for the assessment of microbial degradation of xylose-containing compounds in soil, water, and other ecosystems, contributing to a better understanding of carbon cycling and nutrient availability in these systems.

InChI:InChI=1/C11H13NO7/c13-8-5-18-11(10(15)9(8)14)19-7-3-1-6(2-4-7)12(16)17/h1-4,8-11,13-15H,5H2/t8-,9+,10-,11-/m1/s1

Upstream product

• 100-02-7 4-nitro-phenol 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 108-91-8 cyclohexylamine 
• 16673-34-0 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide 
• 56379-88-5 cyclohexylcarbamic acid phenyl ester 
• 223253-87-0 4-[2-(2,2,2-trifluoroacetamido)ethyl]benzenesulfonyl chloride 
• 458-85-5 2,2,2-trifluoro-N-(2-phenylethyl)acetamide 
• 64-04-0 phenethylamine 
• 33924-54-8 4-(2-[(5-chloro-2-methoxyphenyl)formamido]ethyl)benzene-1-sulfonyl chloride 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 3438-16-2 5-chloro-2-methoxybenzoic acid 
• 33924-49-1 DK₁₃ 
• 201230-82-2 carbon monoxide 
• 3173-53-3 Cyclohexyl isocyanate 

Downstream Products

• 643758-65-0 p-Nitrophenyl 2,3-di-O-benzoyl-α-L-arabinopyranoside 
• 100-02-7 4-nitro-phenol 
• 1089715-92-3 p-amidophenyl-α-L-arabinopyranoside 

Relevant articles and documents

Total Synthesis of Glipizide and Glibenclamide in Continuous Flow

Glipizide and glibenclamide remain some of the widely prescribed antidiabetic sulfonylurea drugs for the treatment of type 2 diabetes mellitus. Herein the authors report on an isocyanate-free synthetic procedure towards the preparation of these on demand drugs at multigram scale using continuous flow technology. The safety concern over the use of isocyanates in most of the existing synthetic routes was dealt with in this present work by using N-carbamates synthesised in situ from activation of amines with chloroformates as safer alternatives. An overall yield of 80–85 % was obtained for the semi-telescoped steps within 10 min total residence time.

Synthesis technology of glibenclamide

The invention provides a novel synthesis technology of a glibenclamide bulk pharmaceuticals. The glibenclamide product is finally prepared by taking sulfamide as a starting raw material through the four steps of a secondary condensation reaction, a compounding reaction, a dealcoholization reaction and refining. The technology has the advantages of being high in yield, low in purity, easy and convenient to operate, suitable for industrialized production and the like.

Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis

A newly designed robust and safe laboratory scale reactor for syntheses under sealed-vessel conditions at 250 °C maximum temperature and 20 bar maximum pressure is presented. The reactor employs conductive heating of a sealed glass vessel via a stainless steel heating jacket and implements both online temperature and pressure monitoring in addition to magnetic stirring. Reactions are performed in 10 mL borosilicate vials that are sealed with a silicone cap and Teflon septum and allow syntheses to be performed on a 2-6 mL scale. This conductively heated reactor is compared to a standard single-mode sealed-vessel microwave instrument with respect to heating and cooling performance, stirring efficiency, and temperature and pressure control. Importantly, comparison of the reaction outcome for a number of different synthetic transformations performed side by side in the new device and a standard microwave reactor suggest that results obtained using microwave conditions can be readily mimicked in the operationally much simpler and smaller conventionally heated device.