58543-17-2

Usage

Uses

Used in Food and Beverage Industry:
REBAUDIOSIDE B(P)(NEW) is used as a nutritive sweetener for its ability to replace sugar in various food and beverage products. It offers a sweet taste without the added calories, making it an ideal choice for health-conscious consumers and those looking to reduce their sugar intake.
Used in Pharmaceutical Industry:
REBAUDIOSIDE B(P)(NEW) is used as a therapeutic agent for the treatment of blood glucose sensitive diseases such as diabetes, high blood pressure, and obesity. Its low glycemic index and minimal impact on blood glucose levels make it a valuable component in the development of medications and supplements aimed at managing these conditions.

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 academic research and scientific papers

Rebaudioside Analogs

The present disclosure provides novel compounds that are steviol derivatives. The compounds generally can be characterized by a structure according to Formula I: wherein A1, L1, and G1 are described herein. Also provided are sweetener compositions comprising the compound described herein either as a sweetener or a sweetener enhancer. Additionally, the compound or the sweetener composition can be included in a product such as a beverage product or a food product, which can reduce the amount of sweetener in the product required to achieve the same sweetness level in an otherwise identical product not including the compound or the sweetener composition.

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%.

Novel Process for the Preparation of Rebaudioside D and Other Related Naturally Occurring Sweetners

A novel process for preparation of Rebaudioside D (RD), and other related naturally occurring sweeteners is provided. RD is a natural sweetening agent which can decrease the bitter aftertaste of steviol glycosides. The said process is suitable for commercial manufacturing by using readily available natural products and nontoxic reagents.

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.

Human psychometric and taste receptor responses to steviol glycosides

Steviol glycosides, the sweet principle of Stevia Rebaudiana (Bertoni) Bertoni, have recently been approved as a food additive in the EU. The herbal non-nutritive high-potency sweeteners perfectly meet the rising consumer demand for natural food ingredients in Europe. We have characterized the organoleptic properties of the most common steviol glycosides by an experimental approach combining human sensory studies and cell-based functional taste receptor expression assays. On the basis of their potency to elicit sweet and bitter taste sensations, we identified glycone chain length, pyranose substitution, and the C16 double bond as the structural features giving distinction to the gustatory profile of steviol glycosides. A comprehensive screening of 25 human bitter taste receptors revealed that two receptors, hTAS2R4 and hTAS2R14, mediate the bitter off-taste of steviol glycosides. For some test substances, e.g., stevioside, we observed a decline in sweet intensity at supra-maximum concentrations. This effect did not arise from allosteric modulation of the hTAS1R2/R3 sweet taste receptor but might be explained by intramolecular cross-modal suppression between the sweet and bitter taste component of steviol glycosides. These results might contribute to the production of preferentially sweet and least bitter tasting Stevia extracts by an optimization of breeding and postharvest downstream processing.

STEVIOL GLYCOSIDE ISOMERS

Steviol glycoside isomers are provided having the formula (II): wherein R1 may be hydrogen, 1-β-D-glucopyranosyl, or 2-(1-β-D-glucopyranosyl)-1-β-D- glucopyranosyl, and R2 may be hydrogen, 1-β-D-glucopyranosyl, 2-(1-β-D-glucopyranosyl)- 1-β-D-glucopyranosyl, 2,3 -bis(1-β-D-glucopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L- rhamnopyranosyl)-1-β-D-glucopyranosyl, 2-(1-α-L-rhamnopyranosyl)-3 -(1-β-D- glucopyranosyl)-1-β-D-glucopyranosyl, or 2-(1-β-D-xylopyranosyl)-3 -(1-β-D- glucopyranosyl)-1-β-D-glucopyranosyl. Methods for making steviol glycoside isomers are also disclosed. These compounds may be present in food and beverage products as non- nutritive sweeteners.