4-Nitrophenyl β-D-cellobioside - ≥98%(HPLC) , CAS No.3482-57-3

CAS: 3482-57-3 Cat. No.: N130852 Molecular Weight: 463.39 Beilstein Registry Number: 100234

GRADE & PURITY ≥98%(HPLC)

Synonyms

A903640 | beta-D-Glucopyranoside, 4-nitrophenyl 4-O-beta-D-glucopyranosyl- (9CI) | (2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | b-D-G

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

4-Nitrophenyl β-D-cellobioside has been used as a substrate to assay β-D-celluliosidase or cellobiohydrolase (exocellulase) activity in the microbial community. It has also been used as a substrate to study the endoglucanase J30 activity. Biochem/physiol Actions

Specifications

Synonyms

A903640 | beta-D-Glucopyranoside, 4-nitrophenyl 4-O-beta-D-glucopyranosyl- (9CI) | (2S, 3R, 4S, 5S, 6R)-2-((2R, 3S, 4R, 5R, 6S)-4, 5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)tetrahydro-2H-pyran-3-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3, 4, 5-triol | b-D-G

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

4-Nitrophenyl β-D-cellobioside is a cellotriose analog, and a chromogenic substrate commonly used for the detection of cellulase activity. Exoglucanase, endoglucanase and β -glucosidase hydrolyze 4-nitrophenyl β-D-cellobioside to form p-nitrophenol (PNP).

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504757565
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504757565
• Canonical Smiles: C1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)O)O)O
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• InChIKey: IAYJZWFYUSNIPN-KFRZSCGFSA-N
• INCHI: 1S/C18H25NO13/c20-5-9-11(22)12(23)14(25)18(30-9)32-16-10(6-21)31-17(15(26)13(16)24)29-8-3-1-7(2-4-8)19(27)28/h1-4,9-18,20-26H,5-6H2/t9-,10-,11-,12+,13-,14-,15-,16-,17-,18+/m1/s1
• Isomeric SMILES: C1=CC(=CC=C1[N+](=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• Molecular Weight: 463.39
• Beilstein: 100234
• Reaxy-Rn: 25442172
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25442172&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: Disaccharides O-glycosyl compounds Nitrobenzenes Nitroaromatic compounds Phenol ethers Phenoxy compounds Oxanes Secondary alcohols Oxacyclic compounds Organic oxoazanium compounds Propargyl-type 1,3-dipolar organic compounds Acetals Polyols Organopnictogen compounds Organonitrogen compounds Organic zwitterions Organic salts Organic oxides Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Phenolic glycoside - Disaccharide - O-glycosyl compound - Nitrobenzene - Phenoxy compound - Nitroaromatic compound - Phenol ether - Monocyclic benzene moiety - Oxane - Benzenoid - C-nitro compound - Organic nitro compound - Secondary alcohol - Allyl-type 1,3-dipolar organic compound - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Acetal - Polyol - Organic oxoazanium - Oxacycle - Organic salt - Organonitrogen compound - Alcohol - Hydrocarbon derivative - Organic oxide - Primary alcohol - Organopnictogen compound - Organic nitrogen compound - 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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in Water(Heat) Faint Yellow to Light Yellow,Clear,50 mg/ml
• Sensitivity: Heat sensitive；Moisture sensitive; Light sensitive
• Specific Rotation[α]: -80.0 to -84.0 deg(C=1, methanol)
• Melt Point(°C): 245°C(dec.)(lit.)
• Molecular Weight: 463.400 g/mol
• XLogP3: -2.600
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 463.133 Da
• Monoisotopic Mass: 463.133 Da
• Topological Polar Surface Area: 224.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 612.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• 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

1. Xiaozan Dai, Guanchen Liu, Quan Zhang, Chao Zhu, Huipeng Gao, Youduo Wu, Chi Cheng, Hailong Lin, Chuang Xue.  (2025)  Novel Transcription Factor TrTRC-1 Controls Amino Acid Biosynthesis to Regulate Cellulase and Xylanase Production in Trichoderma reesei.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:41371707] [10.1021/acs.jafc.5c07274]

2. Yixin Sun, Qi Sun, Tiantian Gao, Shumin Ren, Xiaomei Hu.  (2025)  Competitive binding of TeXlnR and TeAmyR regulates cellulase production in Talaromyces endophyticus.  Synthetic and Systems Biotechnology,      [PMID:41280277] [10.1016/j.synbio.2025.10.010]

3. Yixin Sun, Qi Sun, Yingying Hou, Chunying Li, Xiaomei Hu.  (2025)  Unveiling the lignocellulose-degrading potential of a novel Talaromyces endophyticus through enzymatic hydrolysis and transcriptomic analysis.  BIOMASS & BIOENERGY,      [PMID:] [10.1016/j.biombioe.2025.108474]