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β-Gentiobiose (gentiobiose; Gentiobiose)

Cat No.:V61966 Purity: ≥98%
β-Gentiobiose (Gentiobiose) is a natural oligosaccharide that promotes fruit ripening.
β-Gentiobiose (gentiobiose; Gentiobiose)
β-Gentiobiose (gentiobiose; Gentiobiose) Chemical Structure CAS No.: 554-91-6
Product category: Saccharides
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
Other Sizes
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Product Description
β-Gentiobiose (Gentiobiose) is a natural oligosaccharide that promotes fruit ripening.
β-Gentiobiose (gentiobiose) (CAS 554-91-6) is a natural disaccharide composed of two D-glucose units linked by a β-1,6-glycosidic bond. It has the molecular formula C₁₂H₂₂O₁₁ and a molecular weight of 342.30 g/mol. β-Gentiobiose is a natural oligosaccharide that promotes fruit ripening. It is extensively studied for its role in carbohydrate chemistry and its applications in biological research. The sugar is particularly important for investigating the enzymatic breakdown and synthesis of β-glucans, which are key components of plant cell walls and fungal cell walls. It also acts as a competitive inhibitor of phosphoglycerol transferase. It is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
Phosphoglycerol transferase (competitive inhibitor); β-glucan-related enzymes. β-Gentiobiose is a competitive inhibitor of phosphoglycerol transferase. It is also used in binding assays to determine if proteins bind to β-1,3-glucans. As a disaccharide component of β-glucans, it is important for investigating the enzymatic breakdown and synthesis of β-glucans.
ln Vitro
β-Gentiobiose is a competitive inhibitor of phosphoglycerol transferase. It is a natural oligosaccharide that promotes fruit ripening. The compound is used in binding assays to determine if coelomic cytolytic factor 1 (CCF-1) binds to β-1,3-glucans. Its in vitro activity includes serving as a substrate or inhibitor in enzymatic studies of carbohydrate metabolism.
ln Vivo
In vivo, β-gentiobiose promotes fruit ripening. It is a natural oligosaccharide found in various plant sources. The compound is used in research to study carbohydrate metabolism, β-glucan synthesis and degradation, and plant physiology. It is not administered as a therapeutic agent but serves as a research tool for studying carbohydrate-related processes.
Enzyme Assay
Non-cell-based assays for β-gentiobiose include enzyme inhibition studies using phosphoglycerol transferase or other carbohydrate-metabolizing enzymes. The compound is incubated with the enzyme and substrate, and enzyme activity is measured by detecting product formation. Competitive inhibition is determined by varying substrate concentrations in the presence of fixed inhibitor concentrations. Binding assays are used to study interactions with β-glucan-binding proteins.
Cell Assay
Cell-based assays for β-gentiobiose are limited, as the compound is primarily used in biochemical and enzymatic studies. In plant cell culture models, the compound’s effects on fruit ripening and cell wall metabolism can be assessed. In microbial culture models, its effects on β-glucan metabolism and microbial growth can be studied.
Animal Protocol
In vivo studies of β-gentiobiose are conducted in plant models to study fruit ripening and carbohydrate metabolism. The compound may be applied to fruits or plants, and ripening parameters, sugar content, and enzyme activities are measured. In animal models, the compound’s effects on carbohydrate metabolism and gut microbiota can be studied.
ADME/Pharmacokinetics
β-Gentiobiose has a molecular formula of C₁₂H₂₂O₁₁ and a molecular weight of 342.30 g/mol. It is a natural disaccharide composed of two D-glucose units linked by a β-1,6-glycosidic bond. Purity is ≥97%. The compound should be stored under recommended conditions. It is intended for research use only.
Toxicity/Toxicokinetics
β-Gentiobiose is generally considered to have low toxicity as a natural sugar. It is not intended for human therapeutic use. Standard laboratory safety practices should be followed when handling this compound.
References

[1]. Gentiobiose: a novel oligosaccharin in ripening tomato fruit. Planta. 2003 Jan;216(3):484-95.

Additional Infomation
6-ObD-glucopyranosyl-D-glucose has reportedly been found in Ascochyta medicaginicola, Gentiana straminea, and other organisms with available data.
β-Gentiobiose (gentiobiose) is a natural disaccharide composed of two D-glucose units linked by a β-1,6-glycosidic bond. It is a natural oligosaccharide that promotes fruit ripening and is extensively studied for its role in carbohydrate chemistry and biological research. The sugar is important for investigating the enzymatic breakdown and synthesis of β-glucans, key components of plant and fungal cell walls. It acts as a competitive inhibitor of phosphoglycerol transferase and is used in binding assays for β-glucan-binding proteins. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H22O11
Molecular Weight
342.30
Exact Mass
342.116
CAS #
554-91-6
PubChem CID
20056559
Appearance
White to off-white solid powder
Density
1.76 g/cm3
Boiling Point
662.8ºC at 760 mmHg
Melting Point
195-197 °C (dec.)
Flash Point
354.6ºC
Index of Refraction
9.5 ° (C=4, H2O)
LogP
-5
Hydrogen Bond Donor Count
8
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
8
Heavy Atom Count
23
Complexity
367
Defined Atom Stereocenter Count
9
SMILES
C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)O)O)O)O
InChi Key
AYRXSINWFIIFAE-UDKQPYHCSA-N
InChi Code
InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9+,10-,11+,12+/m0/s1
Chemical Name
(2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexanal
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O: 33.33 mg/mL (97.37 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9214 mL 14.6071 mL 29.2141 mL
5 mM 0.5843 mL 2.9214 mL 5.8428 mL
10 mM 0.2921 mL 1.4607 mL 2.9214 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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