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Rebaudioside N

Alias: REBAUDIOSIDE N; 1220616-46-5; RefChem:178704; ((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) (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,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] (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.:V33537 Purity: ≥98%
Rebaudioside N is a small steviol glycoside extracted from the leaves of Stevia rebaudiana Bertoni.
Rebaudioside N
Rebaudioside N Chemical Structure CAS No.: 1220616-46-5
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 N is a small steviol glycoside extracted from the leaves of Stevia rebaudiana Bertoni. Rebaudioside N (Reb N) is a minor steviol glycoside isolated from the leaves of Stevia rebaudiana Bertoni . It belongs to the ent-kaurane diterpene glycoside family with the molecular formula C₅₆H₉₀O₃₂ and a molecular weight of approximately 1275.29 g/mol . Rebaudioside N is a high-intensity natural sweetener valued for its non-caloric properties and has been recognized as Generally Recognized as Safe (GRAS) by the FEMA (Flavor and Extract Manufacturers Association) as listed in GRAS List 31 . The compound is a minor component, meaning it is present in smaller quantities in stevia leaves compared to major glycosides like rebaudioside A .
Biological Activity I Assay Protocols (From Reference)
Targets
Rebaudioside N (Reb N) primarily targets and activates the human sweet taste receptor, a heterodimeric G protein-coupled receptor composed of T1R2 and T1R3 subunits . Research on steviol rebaudiosides has demonstrated that these compounds can bind to four different sites on the T1R2/T1R3 receptor complex, including the Venus Flytrap Domains (VFD2 and VFD3) and the transmembrane domains (TMD2 and TMD3) . A total of nine different binding pockets have been identified on the human sweet taste receptor, and the binding of steviol rebaudiosides to multiple sites leads to different signal transduction processes .
ln Vitro
The compound is primarily characterized by its physicochemical properties. It has a predicted solubility of 0.023 g/L in water at 25°C, indicating that it is practically insoluble . Based on its structural similarity to other steviol glycosides, Reb N is expected to be metabolized by gut microflora through deglycosylation to the common aglycone steviol, though specific in vitro metabolic studies for Reb N are not detailed.
ln Vivo
As a member of the steviol glycoside family, Reb N is expected to share similar biological properties with other rebaudiosides, including non-caloric sweetening and potential prebiotic-like effects, though specific in vivo study details are not provided.
Enzyme Assay
Research on the broader class of steviol rebaudiosides has employed heterologous cell-based assays with HEK-293 cells overexpressing the T1R2/T1R3 heterodimer to study sweet taste receptor binding . For membrane protein stabilization, tools such as DIBMA (diisobutylene-maleic acid) Glycerol and Rho1D4-MagBeads have been used to preserve the native lipidic environment of the receptors during binding studies . Computational docking studies have revealed that steviol rebaudiosides can bind to nine different binding pockets on the sweet taste receptor .
ADME/Pharmacokinetics
esearch on the broader class of steviol rebaudiosides has employed heterologous cell-based assays with HEK-293 cells overexpressing the T1R2/T1R3 heterodimer to study sweet taste receptor binding . For membrane protein stabilization, tools such as DIBMA (diisobutylene-maleic acid) Glycerol and Rho1D4-MagBeads have been used to preserve the native lipidic environment of the receptors during binding studies . Computational docking studies have revealed that steviol rebaudiosides can bind to nine different binding pockets on the sweet taste receptor .
Toxicity/Toxicokinetics
Rebaudioside N (Reb N) is classified as not a hazardous substance or mixture according to safety data sheets, with no GHS hazard labeling elements required . The compound is not listed as a carcinogen by NTP, IARC Monographs, OSHA, or ACGIH . The product is explicitly labeled for research use only and not for human or veterinary use . Rebaudioside N has been recognized as Generally Recognized as Safe (GRAS) by FEMA (GRAS List 31) . However, the toxicological effects of this product have not been thoroughly studied . Storage recommendations: powder at -20°C in dry, dark conditions for up to 1 year; in solvent at -20°C for 1 month .
References

[1]. Isolation, NMR Spectral Analysis and Hydrolysis Studies of a Hepta Pyranosyl Diterpene Glycoside from Stevia rebaudiana Bertoni. Biomolecules. 2013 Sep 30;3(4):733-40.

Additional Infomation
Rebaudioside N (Reb N) is a minor steviol glycoside naturally present in trace amounts in Stevia rebaudiana leaves . It has the CAS number 1220616-46-5, a molecular weight of 1275.3 g/mol, and a purity specification of ≥98% by HPLC . The IUPAC name describes a complex structure with multiple glucose and rhamnose sugar moieties attached to the steviol aglycone . The compound is a white powder with a solubility that is practically insoluble in water (0.023 g/L at 25°C) . The InChI Key is AKEKAGBWNXIWSS-ZFXKUSSPSA-N . The compound is covered in research related to the binding mechanisms of steviol rebaudiosides to the human sweet taste receptor, which has identified nine different binding pockets on the T1R2/T1R3 receptor complex .
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C56H90O32
Molecular Weight
1275.2946
Exact Mass
1274.54
CAS #
1220616-46-5
PubChem CID
92023638
Appearance
Typically exists as solid at room temperature
LogP
-5.5
Hydrogen Bond Donor Count
19
Hydrogen Bond Acceptor Count
32
Rotatable Bond Count
18
Heavy Atom Count
88
Complexity
2380
Defined Atom Stereocenter Count
36
SMILES
O([C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])O[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])[C@@]12C(=C([H])[H])C([H])([H])[C@]3(C([H])([H])C([H])([H])[C@]4([H])[C@@](C(=O)O[C@@]5([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O5)O[H])O[C@@]5([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O5)O[H])O[H])O[H])O[C@@]5([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])[H])O5)O[H])O[H])O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])[H])[C@]3([H])C([H])([H])C1([H])[H])C2([H])[H]
InChi Key
AKEKAGBWNXIWSS-ZFXKUSSPSA-N
InChi Code
InChI=1S/C56H90O32/c1-19-12-55-10-6-26-53(3,8-5-9-54(26,4)52(76)87-50-44(85-46-38(72)34(68)28(62)20(2)77-46)42(32(66)24(16-60)81-50)83-47-39(73)35(69)29(63)21(13-57)78-47)27(55)7-11-56(19,18-55)88-51-45(86-49-41(75)37(71)31(65)23(15-59)80-49)43(33(67)25(17-61)82-51)84-48-40(74)36(70)30(64)22(14-58)79-48/h20-51,57-75H,1,5-18H2,2-4H3/t20-,21+,22+,23+,24+,25+,26-,27-,28-,29+,30+,31+,32+,33+,34+,35-,36-,37-,38+,39+,40+,41+,42-,43-,44+,45+,46-,47-,48-,49-,50-,51-,53+,54+,55+,56-/m0/s1
Chemical Name
[(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] (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
Synonyms
REBAUDIOSIDE N; 1220616-46-5; RefChem:178704; ((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) (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,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] (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 0.7841 mL 3.9206 mL 7.8413 mL
5 mM 0.1568 mL 0.7841 mL 1.5683 mL
10 mM 0.0784 mL 0.3921 mL 0.7841 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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