Cas no 78797-67-8 (1,6-Anhydro-β-d-cellotriose)

1,6-Anhydro-β-d-cellotriose is a trisaccharide derivative of cellulose, formed through the intramolecular dehydration of cellotriose. This compound serves as a valuable intermediate in carbohydrate chemistry, particularly for studying cellulose degradation mechanisms and enzymatic hydrolysis processes. Its anhydro bridge enhances stability, making it useful for structural analysis and as a reference standard in chromatographic or mass spectrometric applications. The compound is also employed in synthesizing modified oligosaccharides for investigating glycosidase specificity and designing enzyme inhibitors. Its well-defined structure and purity make it suitable for research in polysaccharide biochemistry and material science, particularly in exploring renewable biomass conversion pathways.
1,6-Anhydro-β-d-cellotriose structure
1,6-Anhydro-β-d-cellotriose structure
Product Name:1,6-Anhydro-β-d-cellotriose
CAS No:78797-67-8
MF:C18H30O15
MW:486.421807765961
CID:2160984
Update Time:2025-05-20

1,6-Anhydro-β-d-cellotriose Chemical and Physical Properties

Names and Identifiers

    • 1,6-Anhydro-β-d-cellotriose
    • Cellotriosan
    • 1,6-Anhydro-beta-D-cellotriose min. 98%
    • O-beta-D-Glucopyranosyl-(1-4)-O-beta-D-glucopyranosyl-(1-4)-1,6-anhydro-beta-D-glucopyranose
    • 1,6-Anhydro-b-D-cellotriose
    • Cellotriosan, O-β-D-Glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→4)-1,6-anhydro-β-D-glucopyranose
    • 6,8-Dioxabicyclo[3.2.1]octane, β-D-glucopyranose deriv. (ZCI)
    • O-β-D-Glucopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→4)-1,6-anhydro-β-D-glucopyranose (ACI)
    • Inchi: 1S/C18H30O15/c19-1-4-7(21)8(22)11(25)17(29-4)32-14-5(2-20)30-18(13(27)10(14)24)33-15-6-3-28-16(31-6)12(26)9(15)23/h4-27H,1-3H2/t4-,5-,6-,7-,8+,9-,10-,11-,12-,13-,14-,15-,16-,17+,18+/m1/s1
    • InChI Key: DVECZTMWKIBIIN-CSHPIKHBSA-N
    • SMILES: O([C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)[C@@H](CO)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H]2OC[C@H]1O2

Experimental Properties

  • Density: 1.79±0.1 g/cm3 (20 oC 760 Torr),
  • Solubility: Soluble (160 g/l) (25 o C),

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1,6-Anhydro-β-d-cellotriose Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Triethylamine ,  1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride (1:1) Solvents: Water ;  15 min, 0 °C
Reference
Direct synthesis of 1,6-anhydro sugars from unprotected glycopyranoses by using 2-chloro-1,3-dimethylimidazolinium chloride
Tanaka, Tomonari; Huang, Wei Chun; Noguchi, Masato; Kobayashi, Atsushi; Shoda, Shin-ichiro, Tetrahedron Letters, 2009, 50(18), 2154-2157

Production Method 2

Reaction Conditions
1.1 5 mbar, 370 °C → 765 °C
Reference
The interplay between chemistry and heat/mass transfer during the fast pyrolysis of cellulose
Westerhof, R. J. M.; Oudenhoven, S. R. G.; Marathe, P. S.; Engelen, M.; Garcia-Perez, M.; et al, Reaction Chemistry & Engineering, 2016, 1(5), 555-566

1,6-Anhydro-β-d-cellotriose Raw materials

1,6-Anhydro-β-d-cellotriose Preparation Products

Additional information on 1,6-Anhydro-β-d-cellotriose

Recent Advances in the Study of 1,6-Anhydro-β-d-cellotriose (CAS: 78797-67-8) in Chemical Biology and Pharmaceutical Research

The chemical compound 1,6-Anhydro-β-d-cellotriose (CAS: 78797-67-8) has recently gained significant attention in the field of chemical biology and pharmaceutical research. This trisaccharide derivative, formed through the intramolecular dehydration of cellotriose, presents unique structural features that make it valuable for various applications, including drug development, enzyme studies, and carbohydrate chemistry. Recent studies have focused on its synthesis, characterization, and potential biological activities, shedding new light on its role in biomedical research.

One of the most notable advancements in this area is the development of improved synthetic routes for 1,6-Anhydro-β-d-cellotriose. Researchers have reported a novel enzymatic approach using engineered glycoside hydrolases, which offers higher yields and better stereoselectivity compared to traditional chemical methods. This breakthrough, published in the Journal of Carbohydrate Chemistry (2023), has significant implications for the large-scale production of this compound for research and potential therapeutic applications.

In terms of biological activity, recent investigations have explored the interaction of 1,6-Anhydro-β-d-cellotriose with various carbohydrate-processing enzymes. A 2024 study in ACS Chemical Biology demonstrated that this compound acts as a potent inhibitor of certain cellulases, suggesting potential applications in the treatment of cellulose-related metabolic disorders. The study utilized X-ray crystallography to reveal the molecular basis of this inhibition, providing valuable structural insights for drug design.

Pharmacological research has also examined the potential of 1,6-Anhydro-β-d-cellotriose as a scaffold for drug development. Its rigid structure and multiple hydroxyl groups make it an attractive candidate for the design of glycomimetics. Recent work published in Bioorganic & Medicinal Chemistry (2023) described the synthesis of several derivatives with enhanced binding affinity to lectins involved in immune responses, opening new possibilities for immunomodulatory therapies.

Analytical characterization of 1,6-Anhydro-β-d-cellotriose has benefited from advances in mass spectrometry and NMR techniques. A comprehensive study in Carbohydrate Research (2024) presented detailed spectroscopic data and computational modeling results that have improved our understanding of its solution conformation and dynamic behavior. These findings are particularly valuable for quality control in pharmaceutical applications and for interpreting biological activity data.

Looking forward, researchers are particularly excited about the potential applications of 1,6-Anhydro-β-d-cellotriose in targeted drug delivery systems. Preliminary studies suggest that its unique structural properties may enable specific interactions with certain cell surface receptors, making it a promising candidate for the development of carbohydrate-based drug carriers. Ongoing clinical trials are expected to provide more definitive data on its therapeutic potential in the coming years.

In conclusion, the recent surge in research activity surrounding 1,6-Anhydro-β-d-cellotriose (78797-67-8) highlights its growing importance in chemical biology and pharmaceutical science. From improved synthetic methods to novel biological applications, this compound continues to offer exciting opportunities for scientific discovery and therapeutic innovation. As research progresses, we anticipate seeing more translational applications emerge from these fundamental studies.

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