Cas no 425427-87-8 (6-Chloro-3-indoxyl-β-D-cellobioside)

6-Chloro-3-indoxyl-β-D-cellobioside is a chromogenic substrate widely used in enzymology and molecular biology for detecting β-glucosidase activity. The compound features a chloro-substituted indoxyl moiety linked to a cellobioside group, which undergoes enzymatic hydrolysis to release 6-chloro-3-indoxyl. Subsequent oxidation yields an insoluble blue-green dimeric indigo derivative, enabling sensitive and specific visualization of enzyme activity. Its high solubility in aqueous buffers and low background interference make it ideal for histochemical staining and microbiological assays. The chloro substitution enhances the stability and signal intensity compared to unmodified indoxyl substrates. This substrate is particularly valuable for studying cellulolytic enzymes, microbial identification, and high-throughput screening applications.
6-Chloro-3-indoxyl-β-D-cellobioside structure
425427-87-8 structure
Product Name:6-Chloro-3-indoxyl-β-D-cellobioside
CAS No:425427-87-8
MF:C20H26ClNO11
MW:491.873546123505
CID:68067
PubChem ID:12001511
Update Time:2025-07-02

6-Chloro-3-indoxyl-β-D-cellobioside Chemical and Physical Properties

Names and Identifiers

    • 6-Chloro-3-indolyl beta-D-cellobioside
    • 2-[6-[(6-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
    • (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(6-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
    • 6-Chloro-3-indolyl-beta-D-cellobiopyranoside
    • C-4830
    • 6-Chloro-3-indolyl b-D-cellobioside
    • 6-CHLORO-3-INDOXYL-BETA-D-CELLOBIOSIDE
    • 425427-87-8
    • AKOS026674398
    • 6-Chloro-3-indoxyl-β-D-cellobioside
    • Inchi: 1S/C20H26ClNO11/c21-7-1-2-8-9(3-7)22-4-10(8)30-19-17(29)15(27)18(12(6-24)32-19)33-20-16(28)14(26)13(25)11(5-23)31-20/h1-4,11-20,22-29H,5-6H2/t11-,12-,13-,14+,15-,16-,17-,18-,19-,20+/m1/s1
    • InChI Key: LPDLZDNDKZIJNA-NQXZFOFXSA-N
    • SMILES: ClC1C=CC2=C(C=1)NC=C2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Computed Properties

  • Exact Mass: 491.11900
  • Monoisotopic Mass: 491.1194383g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 8
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 33
  • Rotatable Bond Count: 6
  • Complexity: 649
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 10
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1.6
  • Topological Polar Surface Area: 194?2

Experimental Properties

  • Density: 1.7±0.1 g/cm3
  • Boiling Point: 834.2±65.0 °C at 760 mmHg
  • Flash Point: 458.3±34.3 °C
  • Refractive Index: 1.716
  • PSA: 194.32000
  • LogP: -2.17580
  • Vapor Pressure: 0.0±3.2 mmHg at 25°C

6-Chloro-3-indoxyl-β-D-cellobioside Security Information

6-Chloro-3-indoxyl-β-D-cellobioside Pricemore >>

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Additional information on 6-Chloro-3-indoxyl-β-D-cellobioside

Comprehensive Analysis of 6-Chloro-3-indoxyl-β-D-cellobioside (CAS No. 425427-87-8): Properties, Applications, and Research Insights

6-Chloro-3-indoxyl-β-D-cellobioside (CAS No. 425427-87-8) is a specialized chromogenic substrate widely utilized in biochemical and enzymatic research. This compound, classified under the indoxyl glycosides family, plays a pivotal role in detecting cellulase activity and other carbohydrate-active enzymes. Its unique structure, featuring a β-D-cellobioside moiety linked to a 6-chloro-3-indoxyl group, enables precise visualization of enzymatic reactions through colorimetric assays. Researchers frequently employ it in microbiology, biotechnology, and industrial enzyme screening due to its high sensitivity and specificity.

The growing demand for enzyme substrates in biofuel production and biodegradation studies has spotlighted compounds like 6-Chloro-3-indoxyl-β-D-cellobioside. With increasing interest in sustainable energy and green chemistry, this substrate aids in optimizing cellulase efficiency—a critical factor in breaking down lignocellulosic biomass. Recent studies also explore its potential in gut microbiome research, where carbohydrate metabolism by microbial enzymes is a hot topic. These applications align with trending searches such as "cellulase assay methods" and "indoxyl substrates for enzyme detection," reflecting its relevance in contemporary science.

From a technical perspective, 6-Chloro-3-indoxyl-β-D-cellobioside exhibits excellent solubility in aqueous buffers, making it ideal for high-throughput screening (HTS) platforms. Its cleavage by β-glucosidases releases a chloroindoxyl derivative, which oxidizes to form an insoluble blue precipitate—a visual marker for enzymatic activity. This mechanism is frequently compared to X-Gal (5-bromo-4-chloro-3-indolyl-β-D-galactopyranoside) in molecular biology, another popular search term among researchers. However, the cellobioside variant offers distinct advantages for cellulose-degrading enzyme studies.

Innovations in enzyme engineering and directed evolution have further amplified the importance of chromogenic substrates like 6-Chloro-3-indoxyl-β-D-cellobioside. For instance, its use in metagenomic library screening helps identify novel cellulolytic enzymes from environmental samples—a technique gaining traction in bioprospecting research. Additionally, its compatibility with fluorescence-based detection systems (when combined with modern instrumentation) addresses the need for multiplex assays, a frequently searched topic in life sciences forums.

Quality control and storage of 6-Chloro-3-indoxyl-β-D-cellobioside require attention to light sensitivity and temperature stability, common concerns highlighted in user queries. Suppliers often recommend storage at -20°C in desiccated conditions to preserve its reactivity. As the scientific community prioritizes reproducibility, detailed protocols for its application—such as those shared in open-access journals—are increasingly sought after, reinforcing the compound's role in standardized research workflows.

In summary, 6-Chloro-3-indoxyl-β-D-cellobioside (CAS No. 425427-87-8) bridges fundamental and applied research, catering to evolving needs in enzyme characterization and biomass conversion. Its alignment with trending topics like "sustainable enzyme solutions" and "high-sensitivity substrates" ensures continued relevance in both academic and industrial settings. Future developments may explore its derivatives for multimodal detection or integration with AI-driven enzyme design—an emerging intersection in biochemical innovation.

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