554-91-6

Basic information

• Product Name: GENTIOBIOSE
• Synonyms: 6-O-beta-D-Glucopyranosyl-D-glucose, Amygdalose;(3R,4S,5S,6R)-6-((((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetraol;6-O-B-D-GLUCOPYRANOSYL-D-GLUCOSE;6-O-BETA-D-GLUCOPYRANOSYL-BETA-D-GLUCOSE;6-O-BETA-D-GLUCOPYRANOSYL-D-GLUCOSE;AMYGDALOSE;BETA-GENTOBIOSE;BETA-GENTIOBIOSE
• CAS NO: 554-91-6
• Molecular Formula: C₁₂H₂₂O₁₁
• Molecular Weight: 342.3
• EINECS: 209-074-0
• Product Categories: carbohydrate;Other APIs;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Disaccharides;Sugars;Dextrins、Sugar & Carbohydrates
• Mol File: 554-91-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 195-197 °C (dec.)
• Boiling Point: 397.76°C (rough estimate)
• Flash Point: 354.6 °C
• Appearance: White to Off-white/Powder
• Density: 1.4149 (rough estimate)
• Vapor Pressure: 2.18E-20mmHg at 25°C
• Refractive Index: 9.5 ° (C=4, H2O)
• Storage Temp.: 0-6°C
• PKA: 12.45±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• Merck: 14,4396
• BRN: 93354
• CAS DataBase Reference: GENTIOBIOSE(CAS DataBase Reference)
• NIST Chemistry Reference: GENTIOBIOSE(554-91-6)
• EPA Substance Registry System: GENTIOBIOSE(554-91-6)

Safety Data

• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 554-91-6(Hazardous Substances Data)

Usage

Chemical Properties

white to off-white fine crystalline powder

Uses

Different sources of media describe the Uses of 554-91-6 differently. You can refer to the following data:
1. A disaccharide composed of two units of D-glucose
2. Gentiobiose was used in binding assays to determine if coelomic cytolytic factor 1 (CCF-1) binds to β-1,3-glucans to stimulate the pro-PO-activating system.

Purification Methods

-Gentiobiose is best purified via the octaacetate which is recrystallised from MeOH, EtOH or better from methyl cellosolve by heating at 80o. The octaacetate (15g) is hydrolysed by suspending it in dry 0.05N NaOMe in MeOH (180mL) for 1hour with occasional shaking at room temperature. Dilute this with H2O to dissolve suspended matter, pass through Amberlite IR-120 and Duolite A-4 columns and the eluate is evaporated under reduced pressure to a syrup. Residual H2O is removed by repeated distillation with absolute EtOH under reduced pressure. The syrup is dissolved in methyl cellosolve (~40mL), filtered, nucleated and placed in an oven at 80o. The crystals are filtered off, washed with absolute EtOH (yield 6.7g, 89%), dried and have m 187-189o. Further recrystallisation from methyl cellosolve gives m 190o, and mutarotates from [] D 28 -1.5o (initial) to +10.6o (final, c 4, H2O). The -octaacetate has m 193o (crystallised from 95% EtOH) and has [] D 20 -5o (c 1.8, CHCl3). [Goldstein & Whelan Methods in Carbohydrate Chemistry I 313 1962, Academic Press, Beilstein 17/7 V 203.]

InChI:InChI=1/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11?,12-/m1/s1

Synthetic route

D-glucose (50-99-7) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
mit Hilfe eines Emulsin-Praeparats aus Mandeln;

amygdalin (29883-15-6) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
With Pd-BaSO4; water Hydrogenation;

O3,O5-<(Ξ)-benzylidene>-O1,O2-isopropylidene-O6-β-D-glucopyranosyl-α-D-glucofuranose → O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
With sulfuric acid

chloroform (67-66-3) + iodine (7553-56-2) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (13032-61-6) + silver oxide + calcium sulfate → levoglucosan (498-07-7) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + gentiotriose + gentiotetraose

Conditions	Yield
Behandeln des Reaktionsprodukts mit Bariummethylat in Methanol;

...Expand

D-glucose (50-99-7) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose

Conditions	Yield
With hydrogenchloride

hydrogenchloride (7647-01-0) + levoglucosan (498-07-7) → D-glucose (50-99-7) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose + cellobiose; product 5: polysaccharides

D-glucose (50-99-7) + water (7732-18-5) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
Einw. von Emulsin;

D-glucose (50-99-7) + water (7732-18-5) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + cellobiose (528-50-7)

Conditions	Yield
Einw. von Emulsin;

hydrogenchloride (7647-01-0) + D-glucose (50-99-7) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose

D-glucose (50-99-7) + sulfuric acid (7664-93-9) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose

Conditions	Yield
at 60 - 120℃; Equilibrium constant;

D-glucose (50-99-7) + aqueous sulfuric acid (0.5n) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose

Conditions	Yield
at 60℃; Rate constant;
at 80℃; Rate constant;
at 100℃; Rate constant;

D-glucose (50-99-7) + aqueous sulfuric acid (1n) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose

Conditions	Yield
at 100℃; Rate constant;

D-glucose (50-99-7) + aqueous sulfuric acid (2n) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + isomaltose

Conditions	Yield
at 100℃; Rate constant;

D-glucose (50-99-7) + water (7732-18-5) → O6-β-D-Glucopyranosyl-D-glucose (554-91-6) + laminaribiose

Conditions	Yield
in Gegenwart von sauren Kationenaustauschern;

amylopectin → D-Fructose (57-48-7) + laminaribiose (584-30-5, 2152-85-4, 2495-70-7, 7313-98-6, 15038-73-0, 16741-21-2, 23745-85-9, 29478-44-2, 33799-30-3, 47307-02-8, 50499-34-8, 50499-35-9, 52485-08-2, 52485-09-3, 52485-10-6, 52485-11-7, 55058-42-9, 71630-16-5, 72597-54-7, 72597-55-8, 72597-57-0, 79952-48-0, 79952-49-1, 93221-80-8, 93221-86-4, 100430-40-8, 103302-12-1, 109432-03-3, 122291-87-6, 123050-23-7, 127912-26-9, 149342-88-1, 150447-75-9) + Cellobiose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 528-50-7) + D-glucose (50-99-7) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
Stage #1: amylopectin at 20 - 265℃; Stage #2: With α-(1 → 4)-amylase In aq. phosphate buffer at 37℃; for 24h; pH=7; Enzymatic reaction;

5,7,3',4'-tetrahydroxyflavonol-3-O-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside (7431-83-6) → quercetol (117-39-5) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
With rhamnodiastase Enzymatic reaction;

isorhamnetin 3-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside → isorhamnetin (480-19-3) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6)

Conditions	Yield
With rhamnodiastase Enzymatic reaction;

ammonium carbamate (1111-78-0) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → C12H23NO10*CH3NO2

Conditions	Yield
With ammonium hydroxide In methanol at 37℃; for 12h;	85%

α-D-glucopyranosyl-1-phosphate (59-56-3) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → β-Glcp-(1->4)-[β-Glcp-(1->6)]-Glcp

Conditions	Yield
With recombinant cellobiose phosphorylase from Clostridium thermocellum ATCC27405 of glycoside hydrolase family 94 at 60℃; for 3h; pH=3.9; aq. acetate buffer; Enzymatic reaction; regioselective reaction;	73%

acetic anhydride (108-24-7) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → β-D-gentiobiose octaacetate (4613-78-9)

Conditions	Yield
With pyridine
With sodium acetate

acetic anhydride (108-24-7) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → O1,O2,O3,O4-Tetraacetyl-O6-(tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranose (58769-76-9)

Conditions	Yield
With zinc(II) chloride

propionic acid anhydride (123-62-6) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → O1,O2,O3,O4-Tetrapropionyl-O6-(tetra-O-propionyl-β-D-glucopyranosyl)-ξ-D-glucopyranose

Conditions	Yield
With pyridine

4-nitro-aniline (100-01-6) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → O2,O3,O4-triacetyl-O6-(tetra-O-acetyl-β-D-glucopyranosyl)-D-glucose-(4-nitro-phenylimine)

Conditions	Yield
With methanol; acetic acid Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;

O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → (1S,2R)-3-β-D-glucopyranosyloxy-1-(1-phenyl-1H-pyrazolo[3,4-b]quinoxalin-3-yl)-propane-1,2-diol (80859-41-2, 122361-52-8, 122441-27-4)

O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → O2,O3,O4,O5-tetraacetyl-O6-(tetra-O-acetyl-β-D-glucopyranosyl)-D-glucononitrile (50711-11-0)

Conditions	Yield
With ethanol; hydroxylamine Erhitzen des Reaktionsprodukts mit Acetanhydrid und Natriumacetat;

O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → 2-oxopropanal (78-98-8)

Conditions	Yield
Einfluss der Alkalikonzentration und der Temperatur auf die Bildung;

O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → O2,O3,O4,O5-tetramethyl-O6-(tetra-O-methyl-β-D-glucopyranosyl)-D-gluconic acid methyl ester (117883-99-5)

Conditions	Yield
With water; bromine; barium benzoate anschliessend mit wss. Natronlauge und Dimethylsulfat erwaemen und Behandeln des Reaktionsprodukts mit Methyljodid und Silberoxid;

thiophenol (108-98-5) + O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → gentibiose diphenyldithioacetal

Conditions	Yield
With trifluoroacetic acid Ambient temperature; 12-15 h;

O6-β-D-Glucopyranosyl-D-glucose (554-91-6) → D-glucose (50-99-7)

Conditions	Yield
With Arthrobacter sp. DL001 α-D-glucoside glucohydrolase; water at 30℃; for 0.5h; pH=5.5; citrate-phosphate buffer; Enzymatic reaction;
With C-terminally His6-tagged Oryza sativa L. β-glucosidase OsTAGG2 In aq. acetate buffer at 37℃; for 0.166667h; pH=5; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;

Upstream product

• 3458-28-4 D-Mannose 
• 69685-27-4 1,2,3,4-tetra-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranose 
• 50-99-7 D-glucose 
• 67-66-3 chloroform 
• 7553-56-2 iodine 
• 13032-61-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 7647-01-0 hydrogenchloride 
• 498-07-7 levoglucosan 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 512-65-2 α-D-galactopyranosyl-(1→6)-O-α-D-glucopyranosyl-(1→2)-[α-D-galactopyranosyl-(1→6)-O-β-D-fructofuranoside] 
• 512-69-6 D-raffinose 
• 31056-63-0 methyl-(O⁶-α-D-galactopyranosyl-β-D-glucofuranoside) 
• 29883-15-6 amygdalin 

Downstream Products

• 3646-73-9 α-D-galactopyranose 
• 902-54-5 6-O-β-D-galactopyranosyl-D-galactose 
• 187394-28-1 4-nitrophenyl (α-D-galactopyranosyl)-(1->6)-α-D-galactopyranoside 
• 50-99-7 D-glucose 
• 57-48-7 D-Fructose 
• 13382-86-0 manninotriose 
• 59-23-4 D-Galactose 
• 4649-46-1 1-O-α-D-galactopyranosylglycerol 
• 534-68-9 (2S,3R,4S,5R,6R)-2-(2-Hydroxy-1-hydroxymethyl-ethoxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 1196681-92-1 C₃₈H₅₅N₅O₁₅ 
• 21675-38-7 melibionic acid 
• 111188-56-8 O⁶-α-D-Galactopyranosyl-D-fructose 
• 17296-19-4 α-D-galactopyranosyl-(1->6)-D-mannose 
• 78-98-8 2-oxopropanal 

Relevant articles and documents

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Hydrolysis of raffinose by diluted acids.

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