Cellobiose is a disaccharide with the formula (C6H7(OH)4O)2O. It is classified as a reducing sugar. In terms of its chemical structure, it is derived from the condensation of a pair of β-glucose molecules forging 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.

Cellobiose
Cellobiose
Names
Preferred IUPAC name
(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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.670 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11?,12+/m1/s1 ☒N
    Key: GUBGYTABKSRVRQ-CUHNMECISA-N ☒N
  • O[C@H]2[C@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](OC(O)[C@@H]2O)CO
Properties
C12H22O11
Molar mass 342.297 g·mol−1
Appearance white, hard powder
Odor odorless
Density 1.768 g/mL
Melting point 203.5 °C (398.3 °F; 476.6 K) (decomposes)
12 g/100mL
Solubility very slightly soluble in alcohol
insoluble in ether, chloroform
log P -5.03
Acidity (pKa) 12.39
Hazards
NFPA 704 (fire diamond)
1
0
0
Safety data sheet (SDS) Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It can be obtained by enzymatic or acidic hydrolysis of cellulose and cellulose-rich materials such as cotton, jute, or paper.[1] Cellobiose can be used as an indicator carbohydrate for Crohn's disease and malabsorption syndrome.[2]

Treatment of cellulose with acetic anhydride and sulfuric acid gives cellobiose octoacetate, which is no longer a hydrogen bond donor (though it is still a hydrogen bond acceptor) and is soluble in nonpolar organic solvents.[3]

ReferencesEdit

  1. ^ Wilson, David B. (2009). "Cellulases and biofuels". Current Opinion in Biotechnology. 20 (3): 295–299. doi:10.1016/j.copbio.2009.05.007. PMID 19502046.
  2. ^ "Human Metabolome Database: Showing metabocard for Cellobiose (HMDB0000055)".
  3. ^ Braun, G. (1943). "α-Cellobiose Octaacetate" (PDF). Organic Syntheses. Collected Volume 2: 124. and Braun, G. (1937). "α-Cellobiose Octaacetate". Organic Syntheses. 17: 36. doi:10.15227/orgsyn.017.0036.