Cellobiose
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Names | |
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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 | |
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3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.007.670 ![]() |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 | |
Safety data sheet (SDS) | Sigma-Aldrich |
NFPA 704 (fire diamond) | ![]()
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Infobox references | |
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.
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]
References[]
- ^ 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.
- ^ [1]
- ^ 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.
- Disaccharides
- Glycerols