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Rebaudioside C

Alias: Rebaudioside C; Dulcoside B; FE0M8Z5L2E; FEMA NO. 4720; DTXSID301019859;
Cat No.:V2711 Purity: ≥98%
Rebaudioside C (Dulcoside B), a natural product that belongs to the family of Steviol Glycosides,is used as natural sweeteners to diabetics and others on carbohydrate-controlled diets.
Rebaudioside C
Rebaudioside C Chemical Structure CAS No.: 63550-99-2
Product category: Endogenous Metabolite
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Rebaudioside C (Dulcoside B), a natural product that belongs to the family of Steviol Glycosides, is used as natural sweeteners to diabetics and others on carbohydrate-controlled diets. Stevia rebaudiana Bertoni is a sweet and nutrient-rich plant belonging to the Asteraceae family. Stevia leaves contain steviol glycosides including stevioside, rebaudioside (A to F), steviolbioside, and isosteviol, which are responsible for the plant's sweet taste, and have commercial value all over the world as a sugar substitute in foods, beverages and medicines. Among the various steviol glycosides, stevioside, rebaudioside A and rebaudioside C are the major metabolites and these compounds are on average 250-300 times sweeter than sucrose. Steviol is the final product of Stevia metabolism. The metabolized components essentially leave the body and there is no accumulation. Beyond their value as sweeteners, Stevia and its glycosdies possess therapeutic effects against several diseases such as cancer, diabetes mellitus, hypertension, inflammation, cystic fibrosis, obesity and tooth decay. Studies have shown that steviol glycosides found in Stevia are not teratogenic, mutagenic or carcinogenic and cause no acute and subacute toxicity.

Rebaudioside C (Reb C) is the third most abundant steviol glycoside isolated from the leaves of Stevia rebaudiana Bertoni. It has a molecular formula of C₄₄H₇₀O₂₂ and a molecular weight of 951.01 g/mol. It is a high-intensity sweetener with a sweetness potency approximately 30 times that of sucrose, but it has limited applications in the food and beverage market due to its low sweetness intensity and high lingering bitterness. It also has low solubility in water. [2]
Biological Activity I Assay Protocols (From Reference)
Targets
Rebaudioside C (Reb C) does not have a defined pharmacological target in these articles. It functions as a high-intensity sweetener by interacting with sweet taste receptors (T1R2/T1R3), but no specific receptor binding data (IC50, Ki, EC50) are reported. The articles focus on its catalytic hydrogenation and enzymatic modification to improve taste properties. [1,2]
ln Vitro
Rebaudioside C (Reb C) was subjected to catalytic hydrogenation using Pd(OH)₂ in EtOH/H₂O (8:2) at room temperature under 55 psi H₂ for 5 days. The resulting mixture of dihydrorebaudioside C1 and dihydrorebaudioside C2 (compounds 6/7) completely lost their sweetness after catalytic reduction, as determined by sensory evaluation at 500 ppm in carbon-treated water at room temperature. The original rebaudioside C had a slow onset of sweetness, was less sweet overall than sucrose (about 2%-3% sucrose equivalence), while the reduced compounds showed no sweetness and moderate astringency. [1]
Rebaudioside C (Reb C) was also enzymatically modified using alternansucrase from Leuconostoc citreum. The enzymatic reaction was carried out at 55°C for up to 48 hours with 0.25% w/v reb C, 1M sucrose in 0.05M citric acid buffer (pH 5.5). The major product was a mono-α-glucosyl rebaudioside C (reb C+1G) with a rare α-1→6 linkage. The molecular weight of reb C+1G was determined to be m/z 1111.5 [M-H]⁻ by LC-MS, corresponding to the addition of one glucose unit to reb C (MW 951). MS/MS product ion scan showed loss of two glucose units to form the main daughter ion at m/z 787.4, indicating that the glucose was added to the C-19 (carboxylic group) glucose. [2]
Enzyme Assay
Rebaudioside C (Reb C) enzymatic modification process: High purity reb C (>95% purity) was prepared at 0.25% w/v with 0.05M citric acid buffer at pH 5.5. Sucrose was prepared to 1M with the same buffer. For enzymatic reactions, 1.00 mL of the 0.25% SG substrate was pipetted into 2-mL vials, followed by addition of appropriate amount of sucrose solution to form various SG:sucrose ratios, and finally addition of various amounts of alternansucrase. Two controls were included: Control-1 consisted of SG and sucrose with no alternansucrase; Control-2 consisted of SG and alternansucrase with no sucrose. The enzymatic reaction was carried out by gently inverting the vials at 55°C up to 48 hours. [2]
Catalytic hydrogenation: Pd(OH)₂ (50 mg) was added to a solution of rebaudioside C (2 g) in EtOH/H₂O (8:2, 100 mL). The mixture was hydrogenated at ambient temperature for 5 days under H₂ pressure at 55 psi. After each day, an aliquot was filtered through Celite and analyzed by HPLC for the absence of starting materials. At the end of hydrogenation, the reaction mixture was filtered through celite and concentrated under vacuum to afford a clear white product. The product was triturated with acetone, filtered and dried under vacuum at 50°C for 48-72 hours. The combined purity of the isomeric mixture (6/7) was >97% by HPLC. [1]
Animal Protocol


References
2017;23(11):1616-1622.
Additional Infomation
Rebaudioside C (Reb C) is the third most abundant steviol glycoside in Stevia rebaudiana leaves. It has a sweetness potency of approximately 30 times that of sucrose, but has limited applications due to low sweetness and high lingering bitterness, as well as low water solubility. [2]
Catalytic hydrogenation results: The C16-C17 methylene double bond in steviol glycosides is regarded as a pharmacophore essential for sweetness. Reduction of this double bond resulted in complete loss of sweetness for rebaudioside C derivatives. The ratio of 17α/17β reduced compounds was observed to be 2:1 for rebaudioside C. [1]
Enzymatic modification results: The mono-α-glucosyl rebaudioside C (reb C+1G) was isolated as a white crystalline material (different from the free-flow white powder form of reb A). Sensory analysis revealed that reb C+1G was sweeter than 2% sucrose, corresponding to a sweetness potency of at least 100 (compared to reb C's potency of 30). Reb C+1G had much less bitter or liquorice-type aftertaste than reb C. The improved sensory properties make it a potential low-cost high-intensity sweetener alternative to expensive reb D and reb M. The α-1→6 linkage is rare in the steviol glycoside family; most α-glucosylated steviol glycoside products in the marketplace are reported as stereo- and regiospecific glycosylation via 1→4 linkage. [2]
It has been reported that stevia (Stevia rebaudiana) contains rebaudioside C, and relevant data is available. See also: Stevia (Stevia rebaudiana) leaves (partial).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C44H70O22
Molecular Weight
951.01
Exact Mass
950.435
CAS #
63550-99-2
Related CAS #
63550-99-2
PubChem CID
60208888
Appearance
White to off-white solid powder
Density
1.6±0.1 g/cm3
Boiling Point
1070.0±65.0 °C at 760 mmHg
Melting Point
186-188ºC
Flash Point
310.5±27.8 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.649
LogP
1.82
Hydrogen Bond Donor Count
13
Hydrogen Bond Acceptor Count
22
Rotatable Bond Count
12
Heavy Atom Count
66
Complexity
1740
Defined Atom Stereocenter Count
26
SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@]34CC[C@H]5[C@@]6(CCC[C@@]([C@H]6CC[C@]5(C3)CC4=C)(C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
InChi Key
QSRAJVGDWKFOGU-WBXIDTKBSA-N
InChi Code
InChI=1S/C44H70O22/c1-17-12-43-10-6-22-41(3,8-5-9-42(22,4)40(58)65-38-33(57)30(54)26(50)20(14-46)61-38)23(43)7-11-44(17,16-43)66-39-35(64-36-31(55)28(52)24(48)18(2)59-36)34(27(51)21(15-47)62-39)63-37-32(56)29(53)25(49)19(13-45)60-37/h18-39,45-57H,1,5-16H2,2-4H3/t18-,19+,20+,21+,22-,23-,24-,25+,26+,27+,28+,29-,30-,31+,32+,33+,34-,35+,36-,37-,38-,39-,41+,42+,43+,44-/m0/s1
Chemical Name
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
Synonyms
Rebaudioside C; Dulcoside B; FE0M8Z5L2E; FEMA NO. 4720; DTXSID301019859;
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)
DMSO:100 mg/mL (105.15 mM)
Water:<100 mg/mL (105.15 mM)
Ethanol:8 mg/mL (8.41 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (2.63 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: 2.5 mg/mL (2.63 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: 2.5 mg/mL (2.63 mM) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.0515 mL 5.2576 mL 10.5151 mL
5 mM 0.2103 mL 1.0515 mL 2.1030 mL
10 mM 0.1052 mL 0.5258 mL 1.0515 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.

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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.
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