cellobiose

Also known as 1-beta-D-Glucopyranosyl-4-D-glucopyranose, 4-beta-d-glucopyranosyl-d-glucopyranose, 4-o-beta-d-glucopyranosyl-d-glucose, 4-O-β-D-glucopyranosyl-D-glucopyranose, 4-β-D-glucopyranosyl-D-glucopyranose, Cellose, D-(+)-cellobiose, D-cellobiose

Cellobiose is a disaccharide with the formula (C6H7(OH)4O)2O. It is classified as a reducing sugar - any sugar that possesses the ability or function of a reducing agent. The chemical structure of cellobiose is derived from the condensation of a pair of glucose molecules forming a β(1→4) bond. It can be hydrolyzed to glucose enzymatically or with acid. Cellobiose has eight free alcohol (OH) groups, one acetal linkage, and one hemiacetal linkage, which give rise to strong inter- and intramolecular hydrogen bonds. It is a white solid.

Chemical data

Formula: C12H22O11
Molecular weight: 342.3 g/mol
IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC([C@@H]([C@H]2O)O)O)CO)O)O)O)O
InChIKey: GUBGYTABKSRVRQ-CUHNMECISA-N
XLogP: -4.7
Polar surface area: 190 Å²
H-bond donors: 8
H-bond acceptors: 11
Formal charge: 0

via PubChem

Research

5,044 papers

Cellobiose lipids: applications, production, and downstream processing.Trends in biotechnology · 2025
Intracellular cellobiose metabolism and its applications in lignocellulose-based biorefineries.Bioresource technology · 2017
Cellobiose elicits immunity in lettuce conferring resistance to Botrytis cinerea.Journal of experimental botany · 2023
Cellobiose phosphorylase from Caldicellulosiruptor bescii catalyzes reversible phosphorolysis via different kinetic mechanisms.Scientific reports · 2022
PHB production from cellobiose with Saccharomyces cerevisiae.Microbial cell factories · 2022

via PubMed

Wikidata facts

Mass: 342.116212

Show 4 more facts

chemical formula: C₁₂H₂₂O₁₁
Commons category: Cellobiose
isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC([C@@H]([C@H]2O)O)O)CO)O)O)O)O
canonical SMILES: C(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)O)CO)O)O)O)O

Sources (3)

via Wikidata · CC0

~2 min read

Article

1 sections

Contents

References

{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 451097269 | ImageFile = Cellobiose skeletal.svg | ImageSize = 300px | ImageName = | ImageClass = skin-invert-image | ImageFile1 = Cellobiose_Molekülbaukasten_9515.JPG | SystematicName = (2Ξ,3R,4R,5S,6R)-6-(Hydroxymethyl)-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,4-triol | OtherNames = | IUPACName = β-D-glucopyranosyl-(1→4)-D-glucopyranose 4-O-β-D-Glucopyranosyl-D-glucopyranose | Section1 = | Section2 = | Section3 = }}