ChemicalBook--->CAS DataBase List--->58543-16-1

58543-16-1

58543-16-1 Structure

58543-16-1 Structure
IdentificationBack Directory
[Name]

REBAUDIOSIDE A
[CAS]

58543-16-1
[Synonyms]

4G-S
Reb A
Rebiana
Pure Via
Reb-A 97
Glycoside X
REBAUDIOSIDE
Glycoside A3
STEVIOSIDE A3
Sooolite!-Pure
Sweetener 4G-S
Rebaudioside A
Steviol Glycoside
REBAUDIOSIDE, 60%
A Rebaudioside A >
MONOGLYCOSYLSTEVIOSIDE
Rebaudioside A (500 mg)
Rebaudioside A (300 mg)
REBAUDIOSIDE A STANDARD
REBAUDIOSIDE A USP/EP/BP
Rebaudioside A 50% (RA50)
REBAUDIOSIDE A(rebiana)(RG)
stock Rebaudioside A 58543-16-1
Glycoside A3, froM Stevia rebaudiana
RebaudiosideA(enzymaticallymodified)
Rebaudioside A, froM Steviarebaudiana
Rebaudioside A, 97%, from Steviarebaudiana
(4α)-13-[(2-O-β-D-glucopyranosyl-3-O-β-D­
glucopyranosyl-β-D-glucopyranosyl)-oxy]kaur-6-en-8-oic acid β-D­
(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
(4R)-13-[(2-O-β-D-Glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-oic acid β-D-glucopyranosyl ester
(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
Kaur-16-en-18-oic acid,13-[(O-b-D-glucopyranosyl-(1?2)-O-[b-D-glucopyranosyl-(1?3)]-b-D-glucopyranosyl)oxy]-, b-D-glucopyranosyl ester, (4a)-
Kaur-16-en-18-oic acid, 13-[(O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl)oxy]-, β-D-glucopyranosyl ester, (4α)-
[EINECS(EC#)]

1592732-453-0
[Molecular Formula]

C44H70O23
[MDL Number]

MFCD00210360
[MOL File]

58543-16-1.mol
[Molecular Weight]

967.01
Chemical PropertiesBack Directory
[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℃
[FEMA ]

4772 | STEVIOL GLYCOSIDE EXTRACT, STEVIA REBAUDIANA, REBAUDIOSIDE A 80%
[refractive index ]

1.662
[storage temp. ]

room temp
[solubility ]

DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
[form ]

neat
[pka]

12.51±0.70(Predicted)
[color ]

White to Off-White
[Odor]

Mild odor
[biological source]

plant
[Optical Rotation]

[α]/D -33.0±3.0°, c = 1% in H2O
[Water Solubility ]

water: soluble
[BRN ]

6470556
[Stability:]

Hygroscopic
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
[InChIKey]

HELXLJCILKEWJH-NCGAPWICSA-N
[LogP]

-1-2.61 at 20-25℃ and pH7
[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.
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Description]

Rebaudioside A is a type of naturally occurring steviol glycoside, which can be obtained from Stevia rebaudiana species of plants. It finds applications as food and beverage sweetener.
Rebaudioside A is a glucosylated steviol glycoside studied and used as a non-glycemic food sweetener.
[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]

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
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P301+P312-P302+P352-P304+P340-P305+P351+P338
[Safety Statements ]

24/25
[WGK Germany ]

3
[RTECS ]

NZ8174800
[REACH Registrations]

Active
[HS Code ]

29389090
[Storage Class]

11 - Combustible Solids
Spectrum DetailBack Directory
[Spectrum Detail]

Rebaudioside A(58543-16-1)1HNMR
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