Cellobiose

Cellobiose
Identifiers
CAS Number	528-50-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17057 ;
ChEMBL	ChEMBL1614877 ;
ChemSpider	388323 ;
DrugBank	DB02061 ;
ECHA InfoCard	100.007.670
KEGG	C00185 ;
PubChem CID	294; 439178;
CompTox Dashboard (EPA)	DTXSID3045984 ;
	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 ; InChI=1/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-CUHNMECIBM;
	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/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). verify (what is ?) Infobox references

Cellobiose is a disaccharide with the formula [HOCH₂CHO(CHOH)₃]₂O. Cellobiose, a reducing sugar, consists of two β-glucose molecules linked by a β(1→4) bond. It can be hydrolyzed to glucose enzymatically or with acid.^[1] 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 can be obtained by enzymatic or acidic hydrolysis of cellulose and cellulose rich materials such as cotton, jute, or paper.

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.^[2]

References

^ Cancerweb.ncl.ac.uk
^ 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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[1] Cancerweb.ncl.ac.uk

[2] 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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