Editing Cellobiose (section)

{{Chembox
| Verifiedfields = changed
| Watchedfields  = changed
| verifiedrevid  = 451097269
| ImageFile      = Cellobiose skeletal.svg
| ImageSize      = 300px
| ImageName      = 
| ImageFile1     = Cellobiose_Molekülbaukasten_9515.JPG
| SystematicName = (2''Ξ'',3''R'',4''R'',5''S'',6''R'')-6-(Hydroxymethyl)-5-<nowiki/>{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2,3,4-triol
| OtherNames     = 
| IUPACName      = 4-''O''-β-<small>D</small>-Glucopyranosyl-<small>D</small>-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&nbsp;g/mL
| MeltingPtC = 203.5
| MeltingPt_notes = (decomposes)
| BoilingPt =
| Solubility = 12&nbsp;g/100&nbsp;mL
| SolubleOther = Very slightly soluble in [[ethanol|alcohol]] <br /> insoluble in [[diethyl ether|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 (C<sub>6</sub>H<sub>7</sub>(OH)<sub>4</sub>O)<sub>2</sub>O. 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 [[glucose|β-glucose]] molecules forming a β(1→4) bond. It can be hydrolyzed to glucose enzymatically or with acid. Cellobiose has eight free [[alcohol (chemistry)|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]].<ref>{{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.}}</ref> Cellobiose can be used as an indicator carbohydrate for Crohn's disease and malabsorption syndrome.<ref>{{Cite web|url=http://www.hmdb.ca/metabolites/HMDB0000055|title=Human Metabolome Database: Showing metabocard for Cellobiose (HMDB0000055)}}</ref>

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.<ref>{{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}}</ref>