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MedKoo Cat#: 461106 | Name: Rebaudioside A
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rebaudioside A, a component of Stevia rebaudiana, is a non-caloric sweetener of natural origin.

Chemical Structure

Rebaudioside A
Rebaudioside A
CAS#58543-16-1

Theoretical Analysis

MedKoo Cat#: 461106

Name: Rebaudioside A

CAS#: 58543-16-1

Chemical Formula: C44H70O23

Exact Mass: 966.4308

Molecular Weight: 967.02

Elemental Analysis: C, 54.65; H, 7.30; O, 38.05

Price and Availability

Size Price Availability Quantity
10mg USD 500.00
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Related CAS #
No Data
Synonym
Rebaudioside A; Pure Via; Stevioside a3; RA 95; RA-95; RA95; Truvia
IUPAC/Chemical Name
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl (4R,4aS,6aR,9S,11aR,11bS)-9-(((2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate
InChi Key
HELXLJCILKEWJH-NCGAPWICSA-N
InChi Code
InChI=1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/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+/m1/s1
SMILES Code
C[C@@]12CCC[C@@](C)(C(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)=O)[C@H]1CC[C@]45[C@H]2CC[C@](C(C5)=C)(O[C@H]6[C@H](O[C@H]7[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O7)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O8)[C@H](O)[C@@H](CO)O6)C4
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Rebaudioside A is a steviol glycoside, α-glucosidase inhibitor with IC50 of 35.01 μg/ml that can inhibit ATP-sensitive K+-channels. In vitro, rebaudioside A stimulated the insulin secretion from MIN6 cells in a dose- and glucose-dependent manner.
In vitro activity:
Isolated rebaudioside-A showed concentration-dependent α-glucosidase inhibitory activity with IC50=35.01 μg/ml. The biotransformation of stevioside present in stevia leaves to rebaudioside-A is a simple, inexpensive, and eco-friendly process that has commercial potential. Reference: Food Chem. 2016 Jun 1;200:154-8. https://pubmed.ncbi.nlm.nih.gov/26830573/
In vivo activity:
The findings of this study indicate that maternal low-calorie sweetener consumption has enduring consequences on the offspring of a mouse perinatal low-calorie sweetener exposure model offspring. Adult male, but not female, offspring from both aspartame- and rebaudioside A-exposed dams displayed increased adiposity and developed glucose intolerance. Reference: JCI Insight. 2023 May 22;8(10):e156397. https://pubmed.ncbi.nlm.nih.gov/37014702/
Solvent mg/mL mM
Solubility
DMSO 0.0 0.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 967.02 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Adari BR, Alavala S, George SA, Meshram HM, Tiwari AK, Sarma AV. Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni. Food Chem. 2016 Jun 1;200:154-8. doi: 10.1016/j.foodchem.2016.01.033. Epub 2016 Jan 9. PMID: 26830573. 2. Ilias AN, Ismail IS, Hamzah H, Mohd Mohidin TB, Idris MF, Ajat M. Rebaudioside A Enhances LDL Cholesterol Uptake in HepG2 Cells via Suppression of HMGCR Expression. Rep Biochem Mol Biol. 2021 Oct;10(3):477-487. doi: 10.52547/rbmb.10.3.477. PMID: 34981026; PMCID: PMC8718780. 3. Park S, Belfoul AM, Rastelli M, Jang A, Monnoye M, Bae H, Kamitakahara A, Giavalisco P, Sun S, Barelle PY, Plows J, Jang C, Fodor A, Goran MI, Bouret SG. Maternal low-calorie sweetener consumption rewires hypothalamic melanocortin circuits via a gut microbial co-metabolite pathway. JCI Insight. 2023 May 22;8(10):e156397. doi: 10.1172/jci.insight.156397. PMID: 37014702. 4. Wang J, Yang H, Li Q, Wu X, Di G, Fan J, Wei D, Guo C. Novel nanomicelles based on rebaudioside A: A potential nanoplatform for oral delivery of honokiol with enhanced oral bioavailability and antitumor activity. Int J Pharm. 2020 Nov 30;590:119899. doi: 10.1016/j.ijpharm.2020.119899. Epub 2020 Sep 22. PMID: 32971177.
In vitro protocol:
1. Adari BR, Alavala S, George SA, Meshram HM, Tiwari AK, Sarma AV. Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni. Food Chem. 2016 Jun 1;200:154-8. doi: 10.1016/j.foodchem.2016.01.033. Epub 2016 Jan 9. PMID: 26830573. 2. Ilias AN, Ismail IS, Hamzah H, Mohd Mohidin TB, Idris MF, Ajat M. Rebaudioside A Enhances LDL Cholesterol Uptake in HepG2 Cells via Suppression of HMGCR Expression. Rep Biochem Mol Biol. 2021 Oct;10(3):477-487. doi: 10.52547/rbmb.10.3.477. PMID: 34981026; PMCID: PMC8718780.
In vivo protocol:
1. Park S, Belfoul AM, Rastelli M, Jang A, Monnoye M, Bae H, Kamitakahara A, Giavalisco P, Sun S, Barelle PY, Plows J, Jang C, Fodor A, Goran MI, Bouret SG. Maternal low-calorie sweetener consumption rewires hypothalamic melanocortin circuits via a gut microbial co-metabolite pathway. JCI Insight. 2023 May 22;8(10):e156397. doi: 10.1172/jci.insight.156397. PMID: 37014702. 2. Wang J, Yang H, Li Q, Wu X, Di G, Fan J, Wei D, Guo C. Novel nanomicelles based on rebaudioside A: A potential nanoplatform for oral delivery of honokiol with enhanced oral bioavailability and antitumor activity. Int J Pharm. 2020 Nov 30;590:119899. doi: 10.1016/j.ijpharm.2020.119899. Epub 2020 Sep 22. PMID: 32971177.
1: Wong RR, Chung SJ, Hong JH, Park S. Sweetness interaction between a novel glycosylated rebaudioside A and various sweeteners in a binary mixture system. Food Sci Biotechnol. 2024 Mar 27;33(13):2999-3007. doi: 10.1007/s10068-024-01552-w. PMID: 39220318; PMCID: PMC11364830. 2: Yang Y, Liu Y, Xu M, Cai J, Li Q, Wan Z, Yang X. Hierarchical Self- Aggregation of Multifunctional Steviol Glycosides in Aqueous Solutions. J Agric Food Chem. 2024 Jul 24;72(29):16438-16448. doi: 10.1021/acs.jafc.4c02386. Epub 2024 Jul 9. PMID: 38981019. 3: Kumar A, Singh S, Rana A, Kumar P, Bhushan S, Pathania VL, Kumar D, Singh S, Arya RK. Assessment of radiosensitivity and enhancing key steviol glycosides in Stevia rebaudiana Bertoni through gamma radiation. Int J Radiat Biol. 2024;100(7):1104-1115. doi: 10.1080/09553002.2024.2362647. Epub 2024 Jun 13. PMID: 38870412. 4: Rafiq MT, Sajid ZA, Khilji SA. Graphene Oxide Nanoparticle-Assisted Promotion of Stevioside, Rebaudioside A, and Selected Biochemical Attributes in Stevia rebaudiana Bertoni. Scientifica (Cairo). 2024 May 31;2024:6693085. doi: 10.1155/2024/6693085. PMID: 38855035; PMCID: PMC11161264. 5: Bracchi I, Morais J, Coelho JA, Ferreira AF, Alves I, Mendes C, Correia B, Gonçalves A, Guimarães JT, Falcão-Pires I, Keating E, Negrão R. The Cardiometabolic Impact of Rebaudioside A Exposure during the Reproductive Stage. Biology (Basel). 2024 Mar 2;13(3):163. doi: 10.3390/biology13030163. PMID: 38534433; PMCID: PMC10967885. 6: Ma S, Ma Y. A sustainable strategy for biosynthesis of Rebaudioside D using a novel glycosyltransferase of Solanum tuberosum. Biotechnol J. 2024 Feb;19(2):e2300628. doi: 10.1002/biot.202300628. PMID: 38403450. 7: Kim Y, Han H, Oh Y, Shin H, Park G, Park S, Manthey JA, Kim Y, Kim Y. A combination of rebaudioside A and neohesperidin dihydrochalcone suppressed weight gain by regulating visceral fat and hepatic lipid metabolism in ob/ob mice. Food Sci Biotechnol. 2023 Aug 26;33(4):913-923. doi: 10.1007/s10068-023-01391-1. PMID: 38371686; PMCID: PMC10866850. 8: Zhu S, Li J, Li Z, Wang Z, Wei Q, Shi F. Effects of non-nutritive sweeteners on growth and intestinal health by regulating hypothalamic RNA profile and ileum microbiota in guinea pigs. J Sci Food Agric. 2024 May;104(7):4342-4353. doi: 10.1002/jsfa.13320. Epub 2024 Feb 8. PMID: 38328855. 9: Morissette A, de Wouters d'Oplinter A, Andre DM, Lavoie M, Marcotte B, Varin TV, Trottier J, Pilon G, Pelletier M, Cani PD, Barbier O, Houde VP, Marette A. Rebaudioside D decreases adiposity and hepatic lipid accumulation in a mouse model of obesity. Sci Rep. 2024 Feb 6;14(1):3077. doi: 10.1038/s41598-024-53587-y. PMID: 38321177; PMCID: PMC10847429. 10: Lin Y, Liang M, Pang H, Wang Z, Bi H, Wei Y, Du L. Production of Gibberellins via a Non-Natural Pathway Using Steviol as a Substrate. J Agric Food Chem. 2024 Jan 10;72(1):540-548. doi: 10.1021/acs.jafc.3c06932. Epub 2023 Dec 22. PMID: 38131295. 11: Go SR, Lee SJ, Ahn WC, Park KH, Woo EJ. Enhancing the thermostability and activity of glycosyltransferase UGT76G1 via computational design. Commun Chem. 2023 Dec 6;6(1):265. doi: 10.1038/s42004-023-01070-6. PMID: 38057441; PMCID: PMC10700650. 12: Andreone A, Kozono ML, Schenk M, Guerrero S. A multidimensional evaluation of the effects of sweetener selection and UV-C treatment on orange juice and pectin-based confectionery gels. J Sci Food Agric. 2024 Mar 30;104(5):3013-3026. doi: 10.1002/jsfa.13193. Epub 2023 Dec 28. PMID: 38053417. 13: Sichanova M, Geneva M, Petrova M, Miladinova-Georgieva K, Kirova E, Nedev T, Tsekova D, Ivanova V, Trendafilova A. Influence of the Abiotic Elicitors Ag Salts of Aspartic Acid Derivatives, Self-Organized in Nanofibers with Monomeric and Dimeric Molecular Structures, on the Antioxidant Activity and Stevioside Content in Micropropagated Stevia rebaudiana Bert. Plants (Basel). 2023 Oct 14;12(20):3574. doi: 10.3390/plants12203574. PMID: 37896037; PMCID: PMC10610515. 14: Liu Y, Tello E, Peterson DG. Impact of rebaudioside A degradation compounds on flavor perception. Food Res Int. 2023 Nov;173(Pt 1):113353. doi: 10.1016/j.foodres.2023.113353. Epub 2023 Aug 4. PMID: 37803656. 15: Williams R, Moazzem MS, Dees J, Hayden M, Traynor M, Cho S. Consumer acceptability of no added sugar pound cakes under blind and informed testing conditions. J Food Sci. 2023 Nov;88(11):4677-4692. doi: 10.1111/1750-3841.16773. Epub 2023 Sep 26. PMID: 37751062. 16: Ptak A, Szewczyk A, Simlat M, Błażejczak A, Warchoł M. Meta-Topolin-induced mass shoot multiplication and biosynthesis of valuable secondary metabolites in Stevia rebaudiana Bertoni bioreactor culture. Sci Rep. 2023 Sep 19;13(1):15520. doi: 10.1038/s41598-023-42619-8. PMID: 37726319; PMCID: PMC10509197. 17: Nicoluci ÍG, da Silva BS, Braga PAC, Bragotto APA. Simultaneous determination of nine high-intensity sweeteners in liquid and powder tabletop sweeteners. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2023 Oct;40(10):1298-1306. doi: 10.1080/19440049.2023.2238836. Epub 2023 Sep 11. PMID: 37695976. 18: Kurek JM, Mikołajczyk-Stecyna J, Krejpcio Z. Steviol glycosides from Stevia rebaudiana Bertoni mitigate lipid metabolism abnormalities in diabetes by modulating selected gene expression - An in vivo study. Biomed Pharmacother. 2023 Oct;166:115424. doi: 10.1016/j.biopha.2023.115424. Epub 2023 Sep 5. PMID: 37677968. 19: Wang Y, Xu P, Wang W, Jia X, Zhu L, Yin H. Oligosaccharides increased both leaf biomass and steviol glycosides content of Stevia rebaudiana. Plant Physiol Biochem. 2023 Sep;202:107937. doi: 10.1016/j.plaphy.2023.107937. Epub 2023 Aug 3. PMID: 37566994. 20: Watanabe T, Fujikawa K, Urai S, Iwaki K, Hirai T, Miyagawa K, Uratani H, Yamagaki T, Nagao K, Yokoo Y, Shimamoto K. Identification, Chemical Synthesis, and Sweetness Evaluation of Rhamnose or Xylose Containing Steviol Glycosides of Stevia (Stevia rebaudiana) Leaves. J Agric Food Chem. 2023 Jul 26;71(29):11158-11169. doi: 10.1021/acs.jafc.3c01753. Epub 2023 Jul 11. PMID: 37432401; PMCID: PMC10375593.