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Rebaudioside J

Alias: Rebaudioside J; RefChem:178703; ((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl) (1R,4S,5R,9S,10R,13S)-13-((2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxan-2-yl)oxy-5,9-dimethyl-14-methylidenetetracyclo(11.2.1.01,10.04,9)hexadecane-5-carboxylate; [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate;
Cat No.:V33259 Purity: ≥98%
Rebaudioside J is a diterpene glycoside found in Stevia rebaudiana.
Rebaudioside J
Rebaudioside J Chemical Structure CAS No.: 1313049-59-0
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Rebaudioside J is a diterpene glycoside found in Stevia rebaudiana. Rebaudioside J (Reb J) is a minor steviol glycoside naturally found in the leaves of Stevia rebaudiana Bertoni . Its natural abundance is extremely low, typically comprising less than 0.5% of the total steviol glycoside content, which has historically made the study and commercial application of this compound challenging . The molecular formula of Rebaudioside J is C₅₀H₈₀O₂₇, and its molecular weight is approximately 1113 g/mol . It is classified as a diterpene glycoside and is considered a high-potency sweetener .
Biological Activity I Assay Protocols (From Reference)
Targets
strong>Rebaudioside J (Reb J) exerts its sweetening effect primarily by binding to and activating the sweet taste receptors (T1R2/T1R3 heterodimer) on the tongue, which are G protein-coupled receptors . When Reb J binds to these receptors, it triggers a conformational change that activates a signal transduction pathway involving G proteins, ultimately leading to the perception of sweetness. Additionally, based on the known properties of structurally similar steviol glycosides, it is plausible that Reb J may also interact with specific human bitter taste receptors, such as hTAS2R4 and hTAS2R14, which are associated with the bitter off-taste often detected in stevia extracts .
ln Vitro
The primary in vitro activity reported for Rebaudioside J (Reb J) relates to its potential health benefits. Studies indicate that Reb J may enhance insulin sensitivity and glucose uptake in cells, potentially through the modulation of signaling pathways such as PI3K/Akt . It has also demonstrated anti-inflammatory properties by inhibiting the production of pro-inflammatory cytokines and has shown antioxidant activity in assays measuring its ability to scavenge free radicals . One study using a diabetic rat model found that the administration of Reb J (at a dose of 500 mg/kg) resulted in significant improvements in glucose tolerance without altering insulin levels, suggesting a direct effect on glucose homeostasis .
ln Vivo
A brief mention of a rat study cited above, which demonstrated improvements in glucose tolerance with no observed adverse effects .
Enzyme Assay
However, a patent by PepsiCo describes an enzymatic method for preparing Rebaudioside J using rebaudioside A as a substrate . The method utilizes a UDP-glycosyltransferase (UGT), specifically a UGT-B enzyme from Oryza sativa (rice), to catalyze the transfer of a rhamnosyl group (donated by UDP-rhamnose) to the steviol backbone, producing Reb J . The reaction is typically carried out in an aqueous system at a temperature of 35-45°C and a pH of 7.5-8.5, often in a phosphate buffer solution . This enzymatic approach allows for the production of high-purity Reb J (≥95%) independent of its low natural abundance .
Cell Assay
The cited in vitro studies on glucose uptake are presumed to have been conducted in relevant cell lines (e.g., human cells), but the specific cell types or detailed protocols are not provided .
Animal Protocol
The single cited study involved diabetic rat models, but the dosage (500 mg/kg) is mentioned without details on administration route, frequency, duration, or group sizes .
ADME/Pharmacokinetics
As a steviol glycoside, Reb J is not expected to be absorbed intact and is likely metabolized by gut microflora to the aglycone steviol, though specific studies for Reb J are not detailed .
Toxicity/Toxicokinetics
Rebaudioside J (Reb J) has been evaluated for safety in various studies. Current evidence suggests that it is well-tolerated with no significant adverse effects reported at typical consumption levels . Long-term studies in rodents have shown no significant adverse effects associated with high doses of this compound, and the no-observed-adverse-effect level (NOAEL) was established at significantly higher doses than typical human consumption levels . All product listings explicitly state that the compound is for research use only and not for human or veterinary therapeutic use . The compound is considered a non-hazardous material with no GHS hazard labeling elements required . Storage recommendations: powder at -20°C in dry, dark conditions for up to 3 years; in solvent at -80°C for 6 months or -20°C for 1 month .
References

[1]. Compositions comprising rebaudioside j. WO2018044588A1.

Additional Infomation
Rebaudioside J (Reb J) is a minor steviol glycoside naturally present in trace amounts in Stevia rebaudiana leaves . It has the CAS number 1313049-59-0, a molecular weight of 1113.15 g/mol, and a purity specification of ≥95-98% by HPLC . Due to its low natural abundance, enzymatic synthesis methods using UDP-glycosyltransferases have been developed for its production, as described in a patent by PepsiCo . This enzymatic method uses rebaudioside A as a substrate and a UGT-B enzyme from Oryza sativa (rice) to catalyze the transfer of a rhamnosyl group, yielding Rebaudioside J with high purity . The compound is being investigated for its potential anti-diabetic, anti-inflammatory, and antioxidant properties, making it a candidate for research into metabolic disorders . Rebaudioside J is also being explored for its potential prebiotic effects, as studies suggest it may positively influence gut microbiota composition by promoting beneficial bacteria and inhibiting pathogenic strains . The InChI Key for Reb J is HINSNOJRHFIMKB-DJDMUFINSA-N .
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C50H80O27
Molecular Weight
1113.1540
CAS #
1313049-59-0
PubChem CID
101797534
Appearance
Typically exists as solid at room temperature
Hydrogen Bond Donor Count
16
Hydrogen Bond Acceptor Count
27
Rotatable Bond Count
15
Heavy Atom Count
77
Complexity
2060
Defined Atom Stereocenter Count
31
Synonyms
Rebaudioside J; RefChem:178703; ((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl) (1R,4S,5R,9S,10R,13S)-13-((2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy)oxan-2-yl)oxy-5,9-dimethyl-14-methylidenetetracyclo(11.2.1.01,10.04,9)hexadecane-5-carboxylate; [(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate;
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 0.8984 mL 4.4918 mL 8.9835 mL
5 mM 0.1797 mL 0.8984 mL 1.7967 mL
10 mM 0.0898 mL 0.4492 mL 0.8984 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

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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
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • 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)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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