Cellobiose

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451097269

| ImageFile = Cellobiose skeletal.svg

| ImageSize = 300px

| ImageName =

| ImageFile1 = Cellobiose_Molekülbaukasten_9515.JPG

| SystematicName = (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

| OtherNames =

| IUPACName = 4-O-β-D-Glucopyranosyl-D-glucopyranose

| Section1 = {{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 528-50-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = BM3MOX055H

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C00185

| PubChem = 294

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB02061

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1614877

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 17057

| PubChem2 = 439178

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 10261

| 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GUBGYTABKSRVRQ-CUHNMECISA-N

}}

| Section2 = {{Chembox Properties

| C=12 | H=22 | O=11

| MolarMass =

| Appearance = White, hard powder

| Odor = Odorless

| Density = 1.768 g/mL

| MeltingPtC = 203.5

| MeltingPt_notes = (decomposes)

| BoilingPt =

| Solubility = 12 g/100 mL

| SolubleOther = Very slightly soluble in alcohol
insoluble in ether, chloroform

| LogP = −5.03

| pKa = 12.39

}}

| Section3 = {{Chembox Hazards

| ExternalSDS = [https://www.sigmaaldrich.com/US/en/sds/sial/22150 Sigma-Aldrich]

| MainHazards =

| FlashPt =

| AutoignitionPt =

| NFPA-H = 1 | NFPA-F = 0 | NFPA-R = 0

}}

}}

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.{{cite journal|doi=10.1016/j.copbio.2009.05.007|pmid=19502046|title=Cellulases and biofuels|journal=Current Opinion in Biotechnology|volume=20|issue=3|pages=295–299|year=2009|last1=Wilson|first1=David B.}} Cellobiose can be used as an indicator carbohydrate for Crohn's disease and malabsorption syndrome.{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB0000055|title=Human Metabolome Database: Showing metabocard for Cellobiose (HMDB0000055)}}

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.{{cite journal|last=Braun|first= G. |title=α-Cellobiose Octaacetate|journal= Organic Syntheses|volume= Collected Volume 2|page= 124 |year=1943|url=http://www.orgsyn.org/Content/pdfs/procedures/CV2P0124.pdf}} and {{cite journal|last=Braun|first= G. |title=α-Cellobiose Octaacetate|journal= Organic Syntheses|volume= 17|page= 36 |year=1937|doi=10.15227/orgsyn.017.0036}}