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Rebaudioside A

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CAS:58543-16-1
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  • CAS:58543-16-1
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Rebaudioside A Basic information
Product Name:Rebaudioside A
Synonyms:(4α)-13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-oxy]kaur-6-en-8-oic acid β-D-glucopyranosyl ester;Rebaudioside A (300 mg);REBAUDIOSIDE A(rebiana)(RG);(4α)-13-[(O-β-D-Glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic Acid β-D-Glucopyranosyl Ester;4G-S;Glycoside A3, froM Stevia rebaudiana;Glycoside X;Pure Via
CAS:58543-16-1
MF:C44H70O23
MW:967.01
EINECS:611-696-6
Product Categories:Miscellaneous Natural Products;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:58543-16-1.mol
Rebaudioside A Structure
Rebaudioside A Chemical Properties
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)
pka12.51±0.70(Predicted)
form Solid
color White to Off-White
OdorMild odor
Optical Rotation[α]/D -33.0±3.0°, c = 1% in H2O
biological sourceplant
Water Solubility water: soluble
BRN 6470556
Stability:Hygroscopic
Cosmetics Ingredients FunctionsSKIN CONDITIONING
InChIKeyHELXLJCILKEWJH-NCGAPWICSA-N
LogP-1-2.61 at 20-25℃ and pH7
Safety Information
Safety Statements 24/25
WGK Germany 3
RTECS NZ8174800
HS Code 29389090
Storage Class11 - Combustible Solids
MSDS Information
Rebaudioside A Usage And Synthesis
DescriptionRebaudioside 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 PropertiesWhite powder
UsesRebaudioside 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.
Usesnatural sweetener to diabetics and others on carbohydrate-controlled diets
UsesRebaudioside 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.
DefinitionRebaudioside 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.
benefitsZero 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 ActivityRebaudioside 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.
SafetyHigh-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
Stevioside

57817-89-7

Sucrose

57-50-1

Rebaudioside A

58543-16-1

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
Rebaudioside A Preparation Products And Raw materials
Raw materialsStevioside-->Sucrose-->Magnesium chloride-->STEVIA-->Sodium Phosphate Monobasic Monohydrate
Preparation ProductsREBAUDIOSIDE B(P)(NEW)-->ISOREBAUDIOSIDE A(P)
Tag:Rebaudioside A(58543-16-1) Related Product Information
CYCLOPENTADECANE METHYL CYCLOHEXANEACETATE ETHYL CYCLOHEXYLACETATE D-(-)-GULOSE Steviol Rebaudioside A Isophytol DELTA 12 CIS TRIDECENOIC ACID METHYL ESTER 4-tert-Butylcyclohexanol 1-VINYLCYCLOHEXANOL 97 CIS-4-TERT-BUTYLCYCLOHEXANOL CYCLOPENTADECANOL BUTYL UNDECYLENATE REBAUDIOSIDE A(P),REBAUDIOSIDE A(RG) REBAUDIOSIDE B(P) Stevioside propyl cyclohexaneacetate hexyl pivalate

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