58543-17-2

Basic information

• Product Name: REBAUDIOSIDE B(P)(NEW)
• Synonyms: REBAUDIOSIDE B(P)(NEW);REBAUDIOSIDEB;(4R)-13-[(2-O-β-D-Glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid;REBAUDIOSIDE A(rebiana)(P);REBAUDIOSIDE B(SH);(4α)-13-[(O-β-D-Glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid;Stevioside a4;Rebaudioside B (100 mg)
• CAS NO: 58543-17-2
• Molecular Formula: C₃₈H₆₀O₁₈
• Molecular Weight: 804.874
• Mol File: 58543-17-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 1000.6 °C at 760 mmHg
• Flash Point: 302.5 °C
• Appearance: /
• Density: 1.53 g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 4.63±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: REBAUDIOSIDE B(P)(NEW)(CAS DataBase Reference)
• NIST Chemistry Reference: REBAUDIOSIDE B(P)(NEW)(58543-17-2)
• EPA Substance Registry System: REBAUDIOSIDE B(P)(NEW)(58543-17-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58543-17-2(Hazardous Substances Data)

Usage

Uses

Rebaudioside B is a steviol glycoside used as a nutritive sweetener and may be used as a replacement for sugar in food and beverages. Useful in the treatment of blood glucose sensitive diseases such as diabetes, high blood pressure, and obesity.

Synthetic route

rebaudioside A (58543-16-1) → rebaudioside B (58543-17-2)

Conditions	Yield
With water; potassium hydroxide at 90℃; for 1h;	98%
With water; potassium hydroxide at 90℃; for 6h;	70%
With water Alkaline conditions;
With potassium hydroxide In water for 1h; Reflux;

stevioside (57817-89-7) → rebaudioside B (58543-17-2)

Conditions	Yield
With potassium hydroxide In ethanol at 110℃; for 1.5h;	90 mg

acetic anhydride (108-24-7) + rebaudioside B (58543-17-2) → C58H80O28

Conditions	Yield
With dmap; triethylamine at 60℃; for 2h;	95%
With dmap; triethylamine at 60℃; for 3h; Temperature; Inert atmosphere;	94%
With sodium acetate at 140℃; for 2.5h;	76%

sophorose (20880-64-2) + rebaudioside B (58543-17-2) → rebaudioside D (63279-13-0)

Conditions	Yield
With cutinase from Thermobifida fusca In methanol; aq. phosphate buffer at 55 - 70℃; for 12h; Solvent; Temperature; Time;	50.2%

1,3-propanesultone (1120-71-4) + rebaudioside B (58543-17-2) → 19-O<(sodiosulfo)propyl>rebaudioside B (93000-19-2)

Conditions	Yield
With potassium hydroxide; potassium carbonate 1.) DMF, RT, 64 h, 2.) DMF, 40 deg C, overnight; Yield given. Multistep reaction;

rebaudioside B (58543-17-2) → [2H4]-16,17-dihydrorebaudioside B

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 760.051 Torr;

rebaudioside B (58543-17-2) → C58H79ClO27

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate / 2.5 h / 140 °C 2: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / 0 - 25 °C View Scheme

Upstream product

• 57817-89-7 stevioside 
• 58543-16-1 rebaudioside A 

Downstream Products

• 63279-13-0 rebaudioside D 

Relevant articles and documents

Validation of an HPLC method for direct measurement of steviol equivalents in foods

Steviol glycosides are intense natural sweeteners used in foods and beverages. Their acceptable daily intake, expressed as steviol equivalents, is set at 0-4 mg/kg body weight. We report the development and validation of a RP-HPLC method with fluorometric detection of derivatized isosteviol, formed by acid hydrolysis of steviol glycosides. Dihydroisosteviol was used as an internal standard. Using this method, the amount of steviol equivalents in commercial steviol glycoside mixtures and different foods can be directly quantified. The method was successfully tested on strawberry jam, low-fat milk, soft drink, yogurt and a commercial mixture of steviol glycosides. Calibration curves were linear between 0.01 and 1.61 mM steviol equivalents, with a quantification limit of 0.2 nmol. The % RSD of intra-day precision varied between 0.4% and 4%, whereas inter-day precision varied between 0.4% and 5%, for high and medium concentrations, and between 3% and 8% for low concentrations. Accuracy of the analysis varied between 99% and 115%.

Quantitation of sweet steviol glycosides by means of a HILIC-MS/MS-SIDA approach

Meeting the rising consumer demand for natural food ingredients, steviol glycosides, the sweet principle of Stevia rebaudiana Bertoni (Bertoni), have recently been approved as food additives in the European Union. As regulatory constraints require sensitive methods to analyze the sweet-tasting steviol glycosides in foods and beverages, a HILIC-MS/MS method was developed enabling the accurate and reliable quantitation of the major steviol glycosides stevioside, rebaudiosides A-F, steviolbioside, rubusoside, and dulcoside A by using the corresponding deuterated 16,17-dihydrosteviol glycosides as suitable internal standards. This quantitation not only enables the analysis of the individual steviol glycosides in foods and beverages but also can support the optimization of breeding and postharvest downstream processing of Stevia plants to produce preferentially sweet and least bitter tasting Stevia extracts.