beta-Gentiobiose

Base Information

• Chemical Name: beta-Gentiobiose
• CAS No.: 5996-00-9
• Molecular Formula: C12H22O11
• Molecular Weight: 342.3
• UNII: N2VA1H3TIQ
• DSSTox Substance ID: DTXSID501317544
• Nikkaji Number: J1.835.677E
• Wikipedia: Gentiobiose
• Wikidata: Q415583
• Metabolomics Workbench ID: 49922
• ChEMBL ID: CHEMBL1360334
• Mol file: 5996-00-9.mol

Synonyms:beta-Gentiobiose;5996-00-9;6-O-beta-D-glucopyranosyl-D-glucopyranose;Gentiobiose, beta-;Gentiobiose, .beta.-;UNII-N2VA1H3TIQ;N2VA1H3TIQ;(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol;Gentiobiose beta-form [MI];6-O-b-D-Glucopyranosyl-b-D-glucopyranose;CHEBI:71422;beta-D-Glcp-(1->6)-beta-D-Glcp;6-o-beta-D-Glucopyranosyl-beta-D-glucose;beta-D-Glucose, 6-o-beta-D-glucopyranosyl-;(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol;beta -Gentiobiose;Glcbeta1-6Glcbeta;Glcb1-6Glcb;SCHEMBL109658;beta-gentiobiose (closed ring);CHEMBL1360334;GTPL12452;DTXSID501317544;beta-D-Glc-(1->6)-beta-D-Glc;AKOS016010483;GENTIOBIOSE .BETA.-FORM [MI];NCGC00142607-01;(4S,5S,2R,3R,6R)-6-{[(4S,5S,2R,3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3, 4,5,6-tetrahydropyran-2-yloxy)]methyl}-2H-3,4,5,6-tetrahydropyran-2,3,4,5-tetr aol;beta-D-glucosyl-(1->6)-beta-D-glucose;6-O-beta-D-glucopyranosyl-beta-D-glucopyranose;6-O-beta-D-Glucopyranosyl-D-glucose Amygdalose;C08240;D90708;(6-O-BETA-D-GLUCOPYRANOSYL-BETA-DGLUCOSE);A830673;beta-D-glucopyranose-(1->6)-beta-D-glucopyranose;Q415583;6- O-(beta-D-Glucopyranosyl)-beta-D-Glucopyranose;beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranose;6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOSE;.beta.-D-Glucopyranose, 6-O-.beta.-D-glucopyranosyl-;.BETA.-D-GLUCOSE, 6-O-.BETA.-D-GLUCOPYRANOSYL-;WURCS=2.0/1,2,1/[a2122h-1b_1-5]/1-1/a6-b1;(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxymethyl]oxane-2,3,4,5-tetrol;(2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2,3,4,5-tetrol

Chemical Property of beta-Gentiobiose

Chemical Property:

• PSA: 189.53000
• LogP: -5.39720
• XLogP3: -4.7
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 342.11621151
• Heavy Atom Count: 23
• Complexity: 382

Purity/Quality:

β-Gentiobiose ≥85% (remainder primarily α-anomer) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)O)O)O)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)O)O)O)O)O)O)O

Technology Process of beta-Gentiobiose

There total 15 articles about beta-Gentiobiose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

neolinustatin (72229-42-6) → β-D-glucose (492-61-5) + linamarin (554-35-8) + β-gentiobiose (5996-00-9)

Guidance literature:

With hydrogenchloride; for 1h; Product distribution; Ambient temperature;

DOI:10.1021/jo01291a027

Reference yield:

pustulan → D-glucose (50-99-7) + β-gentiobiose (5996-00-9)

Guidance literature:

With trichoderma harzianum fungus pustulanase; In aq. acetate buffer; at 40 ℃; pH=5; Temperature; Kinetics; Enzymatic reaction;

DOI:10.1016/j.carres.2020.108211

Reference yield:

2,6-dihydroxy-4-methoxyacetophenone 2-O-β-D-gentiobioside (63013-34-3,60197-59-3) → 2,6-dihydroxy-4-methoxy-acetophenone (7507-89-3) + β-gentiobiose (5996-00-9)

Guidance literature:

With water; hydrogen cation;

DOI:10.1007/BF00630378

upstream raw materials:

neolinustatin

2,6-dihydroxy-4-methoxyacetophenone 2-O-β-D-gentiobioside

6²-β-D-glucopyranosyl-laminaratriose

azukisaponin VI

Downstream raw materials:

formic acid

O-β-D-glucopyranosylglycolic acid

(S)-6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexane-1,2,3,4,5-pentaol

2-O-β-D-Glucopyranosyl-D-erythronic acid