4-Nitrophenyl β-D-xylopyranoside - Moligand™,≥98% , CAS No.2001-96-9

CAS: 2001-96-9 Cat. No.: N130864 Molecular Weight: 271.22 Beilstein Registry Number: 90066 EC Number: 217-897-1

GRADE & PURITY Moligand™, ≥98%

Synonyms

DTXSID801303045 | 4-Nitrophenyl beta-D-xyloside | beta-D-xylopyranoside, 4-nitrophenyl | 4-Nitrophenyl-?-D-xylopyranoside | 3-Nitrophenyl b-D-xylopyranoside | CHEBI:90148 | p-Nitrophenyl beta-xylopyranoside | p-Nitrophenyl-beta-D-xyloside | cyanopyrimidin

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Substrate for the colorimetric assay of β-D-xylosidase. Also shown to disrupt proteoglycan biosynthesis in vivo.

Specifications

Synonyms

DTXSID801303045 | 4-Nitrophenyl beta-D-xyloside | beta-D-xylopyranoside, 4-nitrophenyl | 4-Nitrophenyl-?-D-xylopyranoside | 3-Nitrophenyl b-D-xylopyranoside | CHEBI:90148 | p-Nitrophenyl beta-xylopyranoside | p-Nitrophenyl-beta-D-xyloside | cyanopyrimidin

Specifications & Purity

Moligand™, ≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756067
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756067
• Canonical Smiles: C1C(C(C(C(O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• IUPAC Name: (2S,3R,4S,5R)-2-(4-nitrophenoxy)oxane-3,4,5-triol
• InChIKey: MLJYKRYCCUGBBV-YTWAJWBKSA-N
• INCHI: 1S/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
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=C(C=C2)[N+](=O)[O-])O)O)O
• WGK Germany: 3
• Molecular Weight: 271.22
• Beilstein: 90066
• Reaxy-Rn: 25808191
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25808191&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Glycosyl compounds
          • Level6 Phenolic glycosides

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Glycosyl compounds
• Direct Parent: Phenolic glycosides
• Alternative Parents: O-glycosyl compounds Pentoses Nitrobenzenes Nitroaromatic compounds Phenol ethers Phenoxy compounds Oxanes Secondary alcohols Oxacyclic compounds Organic oxoazanium compounds Propargyl-type 1,3-dipolar organic compounds Polyols Acetals Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - O-glycosyl compound - Pentose monosaccharide - Nitrobenzene - Phenoxy compound - Nitroaromatic compound - Phenol ether - Monocyclic benzene moiety - Monosaccharide - Oxane - Benzenoid - C-nitro compound - Organic nitro compound - Secondary alcohol - Acetal - Oxacycle - Organic oxoazanium - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Polyol - Allyl-type 1,3-dipolar organic compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Alcohol - Organic zwitterion - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Sensitivity: heat & Moisture sensitive
• Specific Rotation[α]: -54.0 to -58.0 deg(C=1, MeOH)
• Melt Point(°C): 158-162℃
• Molecular Weight: 271.220 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 271.069 Da
• Monoisotopic Mass: 271.069 Da
• Topological Polar Surface Area: 125.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 313.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

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3. Wu Zongzhan, Dou Wenyu, Yang Xiaolin, Niu Tengfei, Han Zhuzhen, Yang Li, Wang Rufeng, Wang Zhengtao.  (2024)  Novel glycosidase from Paenibacillus lactis 154 hydrolyzing the 28-O-β-d-glucopyranosyl ester bond of oleanane-type saponins.  APPLIED MICROBIOLOGY AND BIOTECHNOLOGY,  108  (1): (1-13).  [PMID:38573330] [10.1007/s00253-024-13109-2]

4. Liu Yucan, Wang Baoyan, Hu Jing, Sun Hongwei, Lv Xintao, Qu Zhiming, Yang Xiaoyong, Wang Gang, Zhang Yanxiang, Zhang Shujun.  (2025)  Effect of Perfluorobutane Sulfonic Acid On Microbial Community and Functional Enzyme of Nitrogen Cycling in Coastal Sediment.  WATER AIR AND SOIL POLLUTION,  236  (12): (1-16).  [PMID:] [10.1007/s11270-025-08433-w]

5. Hao Liu, Min Huang, Shuxin Wei, Xiaowen Wang, Yaqin Zhao, Zhengyang Han, Xianfeng Ye, Zhoukun Li, Yanling Ji, Zhongli Cui, Yan Huang.  (2024)  Characterization of a multi-domain exo-β-1,3-galactanase from Paenibacillus xylanexedens.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38582482] [10.1016/j.ijbiomac.2024.131413]

6. Bin-Chun Li, Weijuan Dong, Bingbing Wu, Yanlong Liu, Na Han, Guo-Bin Ding.  (2025)  Characterization of a Thermophilic and Acidophilic GH78 α-L-Rhamnosidase from Thermotoga sp. 2812B Capable of Efficiently Hydrolyzing a Variety of Natural Flavonoid Diglycosides.  Biomolecules,  16  (1): (68).  [PMID:41594608] [10.3390/biom16010068]

7. Shuai Zhao, Ye Xue, Ruiyao Chen, Xiangyi Ge, Ning An, Yawei Shi.  (2026)  Revealing an environmentally friendly process for degradation of walnut green husk by Klebsiella variicola M6 and β-xylosidase: Characterization and application.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2026.119245]