Rebaudioside A

Rebaudioside A Property

Melting point:

235°C(lit.)

Boiling point:

1102.8±65.0 °C(Predicted)

Density 

1.59±0.1 g/cm3(Predicted)

vapor pressure 

0-1198Pa at 20-50℃

refractive index 

1.662

FEMA 

4601 | REBAUDIOSIDE A

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Sparingly)

form 

Solid

pka

12.51±0.70(Predicted)

color 

White to Off-White

Odor

Mild odor

biological source

plant

optical activity

[α]/D -33.0±3.0°, c = 1% in H2O

Water Solubility 

water: soluble

BRN 

6470556

Stability:

Hygroscopic

LogP

-1-2.61 at 20-25℃ and pH7

Safety

Safety Statements 

24/25

WGK Germany 

3

RTECS 

NZ8174800

HS Code 

29389090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Rebaudioside A Chemical Properties,Usage,Production

Description

Rebaudioside A is a natural non-caloric sweetener. It is one of the predominant steviol glycosides isolated from S. rebaudiana leaves. It increases glucagon-like peptide 1 (GLP-1) secretion in a 2-dimensional mouse intestine model. In a two bottle preference test, mice drink more water containing rebaudioside A than unsweetened water, though saccharin-sweetened water is still preferred. Rebaudioside A is metabolized by gut microbiota to steviol , a compound whose safety is widely studied. Consumption of rebaudioside A formulations by pre-diabetic patients did not increase fasting or 2 hour plasma glucose levels or insulin levels.

Chemical Properties

White powder

Uses

Rebaudioside A is a glycoside from the stevia plant. Rebaudioside A is used as a sweetener with sweetness about 300 times that of sugar with negligible effect on blood glucose. As a result, Rebaudiosi de A is known for its application in treatment of many diseases like diabetes, high blood pressure and weight loss in some places. It is used as a food additive and in dietary supplements.

Uses

natural sweetener to diabetics and others on carbohydrate-controlled diets

Uses

Rebaudioside A is a natural, highly processed calorie free sweetener obtained from the leaves of the plant stevia rebaudiana bertoni. it is a steviol glycoside in which the steviol’s carboxyl and hydroxyl hydrogen atom is replaced with glucose, it has three linked glucose molecules at the hydroxyl site. rebaudiana (reb a) is 300–400 times sweeter than sugar and the least bitter of the glycosides. it is ph and heat stable with good solubility in water. uses include beverages, table top sweetener, general foods. it is also termed reb a, stevia extract, stevia.

Definition

Rebaudioside A is a rebaudioside that is rubusoside in which the hydroxy groups at positions 3 and 4 of the beta-D-glucopyranosyloxy group at the 13alpha position have both been converted to the corresponding beta-D-glucopyranoside. It has a role as a sweetening agent. It is a beta-D-glucoside, a tetracyclic diterpenoid and a rebaudioside. It derives from a rubusoside and a beta-D-Glcp-(1->2)-[beta-D-Glcp-(1->3)]-beta-D-Glcp.

benefits

Zero calories
No carbohydrate
Does not raise blood glucose or insulin levels (Zero Index Glycemic), safe for people with diabetes
Keto, Vegan, and Gluten-Free

Biological Activity

Rebaudioside A is a natural non-caloric sweetener. It is one of the predominant steviol glycosides isolated from S. rebaudiana leaves. It increases glucagon-like peptide 1 (GLP-1) secretion in a 2-dimensional mouse intestine model. In a two bottle preference test, mice drink more water containing rebaudioside A than unsweetened water, though saccharin-sweetened water is still preferred. Rebaudioside A is metabolized by gut microbiota to steviol, a compound whose safety is widely studied. Consumption of rebaudioside A formulations by pre-diabetic patients did not increase fasting or 2 hour plasma glucose levels or insulin levels.

Safety

High-purity (95% minimum) of individual or combined steviol glycosides can be considered as GRAS (Generally Recognized as Safe) by the FDA. For example, FDA had no questions regarding Guilin Layn's conclusion that its reb A (≥97% by weight (w/w)) is GRAS as a table top sweetener and as a general purpose sweetener in foods, excluding meat and poultry products and infant formulas.
Its safety has also been approved by the EFSA, JECFA, FSANZ and other authorities.

Synthesis

A new structure based on (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,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((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-methylcyclohepta[a]naphthalene-4-carboxylic acid ester and sucrose were used as raw materials, and the general procedure for the synthesis of rebaudioside A was as follows: firstly, the expression in E. coli of pEUGT- SUS vector in E. coli, followed by collecting the cells and washing them twice with potassium phosphate buffer (100 mM, pH 7.2). Next, the cells were broken by sonication in an ice-water bath and centrifuged at 4°C to remove cellular debris to obtain a lysate supernatant containing soluble proteins. This supernatant is the crude extract. The total protein concentration of the crude extract was determined by the Bradford method using bovine serum albumin (BSA) as a standard. Finally, rebaudioside A was synthesized by reacting the substrate acaricide with an equal volume of the crude extract in potassium phosphate buffer (100 mM, pH 7.2) containing different concentrations of UDP-glucose or UDP, sucrose, and 3 mM MgCl2 at 30 °C.

References

[1] Bioscience, Biotechnology and Biochemistry, 2016, vol. 80, # 1, p. 67 - 73