Cellobiose

Title: Cellobiose
CAS Registry Number: 528-50-7
CAS Name: 4-O-b-D-Glucopyranosyl-D-glucose
Additional Names: b-cellobiose; cellose; 4-(b-D-glucosido)-D-glucose
Molecular Formula: C12H22O11
Molecular Weight: 342.30
Percent Composition: C 42.11%, H 6.48%, O 51.41%
Literature References: Unit of cellulose and lichenin. Does not occur free in nature, or as glucoside. Prepn from cotton: Braun, Org. Synth. coll. vol. II, 122, 124 (1943). Prepn from cell-free enzymatic hydrolyzate of cellulose: Whistler, Smart, J. Am. Chem. Soc. 75, 1916 (1953). Structure: Haworth, Hirst, J. Chem. Soc. 119, 193 (1923); Charlton et al., ibid. 1926, 89; Zemplén, Ber. 59, 1254 (1926); Haworth et al., J. Chem. Soc. 1927, 2809; Peterson, Spencer, J. Am. Chem. Soc. 49, 2822 (1927); Helferich et al., Ber. 63, 992 (1930); Hess, Dziengel, ibid. 68, 1594 (1935); Hassid, Ballou in The Carbohydrates, W. Pigman, Ed. (Academic Press, New York, 1957) p 490. Synthesis: Haskins et al., J. Am. Chem. Soc. 64, 1289 (1942). Review: Pazur in The Carbohydrates vol. 2A, W. Pigman et al., Eds. (Academic Press, New York, 2nd ed., 1970) pp 109-110; R. G. Edwards, Dev. Food Carbohydr. 2, 229-273 (1980).
Properties: Minute crystals from dil alcohol which retain 0.25 to 0.50 mol water after drying in vacuo. Indifferent taste. Dec 225°. Shows mutarotation. [a]D20 +14.2° ® +34.6° (15 hrs, c = 8). One gram dissolves in 8 ml water, in 1.5 ml boiling water. Almost insol in abs alc and ether. Reduces Fehling's soln. Hydrolysis with acid or emulsin yields 2 mols b-D-glucose. Not fermented by brewers' yeast, maltase, or invertase.
Optical Rotation: [a]D20 +14.2° ® +34.6° (15 hrs, c = 8)
Derivative Type: Octaacetyl-aldehydro-cellobiose
Molecular Formula: C28H38O19
Molecular Weight: 678.59
Percent Composition: C 49.56%, H 5.64%, O 44.80%
Properties: mp 105-110°. [a]D20 +17.7° (c = 3 in chloroform).
Melting point: mp 105-110°
Optical Rotation: [a]D20 +17.7° (c = 3 in chloroform)
Derivative Type: Octaacetyl-a-cellobiose
Molecular Formula: C28H38O19
Molecular Weight: 678.59
Percent Composition: C 49.56%, H 5.64%, O 44.80%
Properties: mp 229°. [a]D20 +41° (c = 6 in chloroform).
Melting point: mp 229°
Optical Rotation: [a]D20 +41° (c = 6 in chloroform)
Derivative Type: Octaacetyl-b-cellobiose
Properties: mp 202°. [a]D20 -14.7° (c = 5 in chloroform).
Melting point: mp 202°
Optical Rotation: [a]D20 -14.7° (c = 5 in chloroform)
Cellocidin Cellophane Celluloid Cellulose Cellulose Acetates

Cellobiose
Cellobiose
Identifiers
CAS number 528-50-7 N
PubChem 439178
ChemSpider 388323 N
DrugBank DB02061
KEGG C00185 N
Jmol-3D images Image 1
Properties
Molecular formula C12H22O11
Molar mass 342.30 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 (decomp)
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
MSDS Sigma-Aldrich
NFPA 704
NFPA 704.svg
0
1
0
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cellobiose is a disaccharide with the formula [HOCH2CHO(CHOH)3]2O. Cellobiose consists of two 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 intra-molecular 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 cannot engage in hydrogen bonding and is soluble in nonpolar organic solvents.[2]