Cellobiose

Cellobiose
Names
	IUPAC name 4-O-β-D-Glucopyranosyl-β-D-glucopyranose
	Systematic 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
CAS Number	528-50-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17057 ;
ChEMBL	ChEMBL1614877 ;
ChemSpider	10261 ;
DrugBank	DB02061 ;
ECHA InfoCard	100.007.670
KEGG	C00185 ;
PubChem CID	294; 439178;
UNII	BM3MOX055H ;
CompTox Dashboard (EPA)	DTXSID001015527 DTXSID3045984, DTXSID001015527 ;
	InChI 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 Key: GUBGYTABKSRVRQ-CUHNMECISA-N ;
	SMILES 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
Chemical formula	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)
Solubility in water	12 g/100 mL
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). verify (what is ?) Infobox references

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 β-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.

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 acetoacetate, of which there is no longer a hydrogen bond donor (though it is still a hydrogen bond acceptor) and possesses aspects of being 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.
^ "Human Metabolome Database: Showing metabocard for Cellobiose (HMDB0000055)".
^ 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.

[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.

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