Cas no 147103-31-9 (4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside)

4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside structure
147103-31-9 structure
Product Name:4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside
CAS No:147103-31-9
MF:C18H25NO13
MW:463.390006780624
CID:100871
PubChem ID:71307218
Update Time:2025-10-29

4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside Chemical and Physical Properties

Names and Identifiers

    • 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside
    • 4-Nitrophenyl2-O-(a-D-glucopyranosyl)-a-D-glucopyranoside
    • 4-NITROPHENYL 2-O-A-D-GLUCOPYRANOSYL-A-D-GLUCOPYRANOSIDE
    • 4-Nitrophenyl 2-O-α-
    • a-D-Glucopyranoside, 4-nitrophenyl2-O-a-D-glucopyranosyl-
    • 4-Nitrophenyl 2-O-alpha-D-Glucopyranosyl-alpha-D-glucopyranoside
    • (2R,3R,4S,5S,6R)-2-(((2R,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
    • alpha-D-Glucopyranoside, 4-nitrophenyl 2-O-alpha-D-glucopyranosyl-
    • 147103-31-9
    • pNP-alpha-Kojobioside
    • W-201307
    • (2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
    • (2R,3R,4S,5S,6R)-2-{[(2R,3R,4S,5S,6R)-4,5-DIHYDROXY-6-(HYDROXYMETHYL)-2-(4-NITROPHENOXY)OXAN-3-YL]OXY}-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL
    • 4-Nitrophenyl 2-O-(a-D-glucopyranosyl)-a-D-glucopyranoside
    • MFCD07369592
    • 4-Nitrophenyl 2-O-alpha-D-glucopyranosyl-alpha-D-glucopyranoside?
    • 4-Nitrophenyl 2-O-?-D-Glucopyranosyl-?-D-glucopyranoside
    • Inchi: 1S/C18H25NO13/c20-5-9-11(22)13(24)15(26)17(30-9)32-16-14(25)12(23)10(6-21)31-18(16)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
    • InChI Key: ZGWCYKZKLZNQQX-TXSAWVTMSA-N
    • SMILES: O([C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)[C@H]1[C@@H](OC2C=CC(=CC=2)[N+](=O)[O-])O[C@H](CO)[C@H]([C@@H]1O)O

Computed Properties

  • Exact Mass: 463.13258985g/mol
  • Monoisotopic Mass: 463.13258985g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 7
  • Hydrogen Bond Acceptor Count: 13
  • Heavy Atom Count: 32
  • Rotatable Bond Count: 6
  • Complexity: 612
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 10
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: nothing
  • Topological Polar Surface Area: 224?2

Experimental Properties

  • Density: 1.70±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 162-164°C
  • Solubility: Slightly soluble (2.1 g/l) (25 o C),

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Additional information on 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside

4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside (CAS 147103-31-9): A Comprehensive Guide to Its Properties and Applications

4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside (CAS 147103-31-9) is a specialized glycoside compound with significant importance in biochemical research and enzymatic studies. This compound, often referred to as a synthetic substrate, is widely used to study α-glucosidase activity, a key enzyme in carbohydrate metabolism. Its unique structure makes it an invaluable tool for researchers investigating glycosidase inhibitors and carbohydrate-processing enzymes.

The molecular structure of 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside features a 4-nitrophenyl group linked to a disaccharide moiety, which consists of two α-D-glucopyranosyl units. This configuration allows it to serve as a chromogenic substrate, releasing 4-nitrophenol upon enzymatic hydrolysis, which can be easily detected spectrophotometrically. This property is particularly useful in high-throughput screening assays for enzyme inhibitors and activators.

In recent years, the demand for 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-??-D-glucopyranoside has increased due to its applications in diabetes research. With the global rise in diabetes cases, researchers are actively exploring α-glucosidase inhibitors as potential therapeutic agents. This compound plays a crucial role in these studies by enabling the measurement of enzyme inhibition kinetics and the evaluation of novel drug candidates.

Another emerging application of CAS 147103-31-9 is in the field of gut microbiome research. Scientists are investigating how gut bacteria metabolize complex carbohydrates, and this compound serves as a model substrate to study microbial glycosidase activity. This research has gained significant attention due to the growing interest in probiotics and prebiotics for maintaining gut health.

The synthesis of 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside involves sophisticated glycosylation techniques, requiring expertise in carbohydrate chemistry. The purity and stability of this compound are critical for research applications, which is why it's typically supplied as a high-purity reagent by specialized biochemical suppliers. Proper storage conditions (usually at -20°C) are essential to maintain its stability over time.

From a commercial perspective, the market for specialized glycosides like CAS 147103-31-9 has been growing steadily. Pharmaceutical companies and research institutions are the primary consumers, using it for drug discovery programs and mechanistic studies of carbohydrate-active enzymes. The compound's price reflects its specialized nature and the complexity of its synthesis.

Quality control of 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside typically involves HPLC analysis and mass spectrometry to ensure the absence of impurities that could affect experimental results. Researchers should always verify the purity and specifications when purchasing this compound, as batch-to-batch consistency is crucial for reproducible scientific results.

In educational settings, this compound serves as an excellent example for teaching advanced concepts in enzyme kinetics and carbohydrate biochemistry. Its visible color change upon hydrolysis makes it particularly useful for classroom demonstrations and laboratory exercises in biochemistry courses at the university level.

The future research directions involving 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside may include its potential application in personalized medicine approaches for metabolic disorders. As our understanding of individual variations in carbohydrate metabolism improves, this compound could play a role in developing tailored therapeutic strategies.

For researchers working with CAS 147103-31-9, it's important to follow proper laboratory safety protocols, even though the compound is not classified as hazardous. Standard precautions for handling biochemical reagents should be observed, including the use of appropriate personal protective equipment and proper waste disposal methods.

The scientific literature contains numerous references to studies utilizing 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside, particularly in journals focusing on enzymology, carbohydrate research, and medicinal chemistry. These publications demonstrate the compound's versatility and continued relevance in cutting-edge research.

As biotechnology continues to advance, the applications of specialized glycosidic substrates like 4-Nitrophenyl 2-O-α-D-Glucopyranosyl-α-D-glucopyranoside are likely to expand. Researchers are encouraged to explore innovative uses for this compound in areas such as biocatalysis, enzyme engineering, and diagnostic assay development.

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