Synonym
Rebaudioside B; Rebaudioside-B; Stevioside a4; Stevioside-a4;
IUPAC/Chemical Name
(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-carboxylic acid
InChi Key
DRSKVOAJKLUMCL-MMUIXFKXSA-N
InChi Code
InChI=1S/C38H60O18/c1-16-11-37-9-5-20-35(2,7-4-8-36(20,3)34(49)50)21(37)6-10-38(16,15-37)56-33-30(55-32-28(48)26(46)23(43)18(13-40)52-32)29(24(44)19(14-41)53-33)54-31-27(47)25(45)22(42)17(12-39)51-31/h17-33,39-48H,1,4-15H2,2-3H3,(H,49,50)/t17-,18-,19-,20+,21+,22-,23-,24-,25+,26+,27-,28-,29+,30-,31+,32+,33+,35-,36-,37-,38+/m1/s1
SMILES Code
C[C@]12[C@]3([C@]4(C[C@](CC3)(O[C@H]5[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H](O)[C@@H](CO)O5)C(C4)=C)CC[C@@]1([C@@](CCC2)(C(O)=O)C)[H])[H]
Purity
>95% (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
>2 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
2934.99.9001
Biological target:
Rebaudioside B is a natural non-caloric sweetener. It is one of the minor steviol glycosides isolated from S. rebaudiana leaves. Rebaudioside C is metabolized by gut microbiota to steviol.
In vitro activity:
Rebaudioside B suffers from poor aqueous solubility and low dissolution rate, which greatly limits its application, especially in beverages. This study discovered that under certain conditions rebaudioside B forms hemihydrate crystal, which has much lower solubility and dissolution rate than commercial powder rebaudioside B product.
Reference: Food Chem. 2020 Jan 30;304:125444. https://pubmed.ncbi.nlm.nih.gov/31491712/
In vivo activity:
To be determined
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
30.0 |
37.27 |
| DMF |
30.0 |
37.27 |
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
804.88
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.
| 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. Dong J, Yang Z. Characterization of a new hemihydrate rebaudioside B crystal having lower aqueous solubility. Food Chem. 2020 Jan 30;304:125444. doi: 10.1016/j.foodchem.2019.125444. Epub 2019 Aug 29. PMID: 31491712.
2. Purkayastha S, Pugh G Jr, Lynch B, Roberts A, Kwok D, Tarka SM Jr. In vitro metabolism of rebaudioside B, D, and M under anaerobic conditions: comparison with rebaudioside A. Regul Toxicol Pharmacol. 2014 Mar;68(2):259-68. doi: 10.1016/j.yrtph.2013.12.004. Epub 2013 Dec 18. PMID: 24361573.
In vitro protocol:
1. Dong J, Yang Z. Characterization of a new hemihydrate rebaudioside B crystal having lower aqueous solubility. Food Chem. 2020 Jan 30;304:125444. doi: 10.1016/j.foodchem.2019.125444. Epub 2019 Aug 29. PMID: 31491712.
2. Purkayastha S, Pugh G Jr, Lynch B, Roberts A, Kwok D, Tarka SM Jr. In vitro metabolism of rebaudioside B, D, and M under anaerobic conditions: comparison with rebaudioside A. Regul Toxicol Pharmacol. 2014 Mar;68(2):259-68. doi: 10.1016/j.yrtph.2013.12.004. Epub 2013 Dec 18. PMID: 24361573.
In vivo protocol:
To be determined
Wu X, Qiao T, Huang J, Li J, Wei S, Yang J, Zhang Y, Li Y. Rebaudioside B Attenuates Lung Ischemia-reperfusion Injury-associated Apoptosis and Inflammation. Recent Adv Inflamm Allergy Drug Discov. 2024 Apr 5. doi: 10.2174/0127722708295154240327035857. Epub ahead of print. PMID: 38584527.
1: Tavarini S, Clemente C, Bender C, Angelini LG. Health-Promoting Compounds in Stevia: The Effect of Mycorrhizal Symbiosis, Phosphorus Supply and Harvest Time. Molecules. 2020 Nov 18;25(22):5399. doi: 10.3390/molecules25225399. PMID: 33218179; PMCID: PMC7698964.
2: Dong J, Yang Z. Characterization of a new hemihydrate rebaudioside B crystal having lower aqueous solubility. Food Chem. 2020 Jan 30;304:125444. doi: 10.1016/j.foodchem.2019.125444. Epub 2019 Aug 29. PMID: 31491712.
3: Zhang SS, Chen H, Xiao JY, Liu Q, Xiao RF, Wu W. Mutations in the uridine diphosphate glucosyltransferase 76G1 gene result in different contents of the major steviol glycosides in Stevia rebaudiana. Phytochemistry. 2019 Jun;162:141-147. doi: 10.1016/j.phytochem.2019.03.008. Epub 2019 Mar 18. PMID: 30897351.
4: Aranda-González I, Moguel-Ordóñez Y, Chel-Guerrero L, Segura-Campos M, Betancur-Ancona D. Evaluation of the Antihyperglycemic Effect of Minor Steviol Glycosides in Normoglycemic and Induced-Diabetic Wistar Rats. J Med Food. 2016 Sep;19(9):844-52. doi: 10.1089/jmf.2016.0014. Epub 2016 Aug 11. PMID: 27513814.
5: Aranda-González I, Moguel-Ordoñez Y, Betancur-Ancona D. Validation of HPLC-UV method for determination of minor glycosides contained in Stevia rebaudiana Bertoni leaves. Biomed Chromatogr. 2015 May;29(5):733-8. doi: 10.1002/bmc.3349. Epub 2014 Oct 9. PMID: 25296637.
6: Purkayastha S, Pugh G Jr, Lynch B, Roberts A, Kwok D, Tarka SM Jr. In vitro metabolism of rebaudioside B, D, and M under anaerobic conditions: comparison with rebaudioside A. Regul Toxicol Pharmacol. 2014 Mar;68(2):259-68. doi: 10.1016/j.yrtph.2013.12.004. Epub 2013 Dec 18. PMID: 24361573.
7: Chaturvedula VS, Prakash I. Hydrogenation of the exocyclic olefinic bond at C-16/C-17 position of ent-kaurane diterpene glycosides of Stevia rebaudiana using various catalysts. Int J Mol Sci. 2013 Jul 26;14(8):15669-80. doi: 10.3390/ijms140815669. PMID: 23896597; PMCID: PMC3759879.
8: Jaworska K, Krynitsky AJ, Rader JI. Simultaneous analysis of steviol and steviol glycosides by liquid chromatography with ultraviolet detection on a mixed-mode column: application to Stevia plant material and Stevia-containing dietary supplements. J AOAC Int. 2012 Nov-Dec;95(6):1588-96. doi: 10.5740/jaoacint.11-435. PMID: 23451373.
9: Prakash I, Campbell M, Chaturvedula VS. Catalytic hydrogenation of the sweet principles of Stevia rebaudiana, Rebaudioside B, Rebaudioside C, and Rebaudioside D and sensory evaluation of their reduced derivatives. Int J Mol Sci. 2012 Nov 16;13(11):15126-36. doi: 10.3390/ijms131115126. PMID: 23203115; PMCID: PMC3509631.
10: Okamoto K, Nakano H, Yatake T, Kiso T, Kitahata S. Purification and some properties of a beta-glucosidase from Flavobacterium johnsonae. Biosci Biotechnol Biochem. 2000 Feb;64(2):333-40. doi: 10.1271/bbb.64.333. PMID: 10737190.
