Name: REBAUDIOSIDE A
SKU: 58543-16-1

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Basic Information

Molecular Structure:
CAS No.:	58543-16-1
Name:	REBAUDIOSIDE A

Formula:	C₄₄H₇₀O₂₃
Molecular Weight:	967.026
Synonyms:	4G-S;Glycoside X;Rebaudioside A;Rebiana;Sooolite!-Pure;Stevioside a3;Sweetener 4G-S;
EINECS:	611-696-6
Density:	1.58 g/cm³
Melting Point:	242-244 °C
Boiling Point:	1103.5 °C at 760 mmHg
Flash Point:	320.2 °C
Safety:	24/25
PSA:	374.13000
LogP:	-5.11390

Synthetic route

: 57817-89-7
stevioside

: 57-50-1
Sucrose

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
With Arabidopsis thaliana sucrose synthase gene; UDP-glucosyltransferase from Stevia rebaudiana, recombinant; magnesium chloride In aq. phosphate buffer at 30℃; for 30h; pH=7.2; Time; Enzymatic reaction;	78%

: 64849-39-4, 104873-42-9
13-O-β-D-glucopyranosyl-19-O-β-D-glucopyranosylsteviol

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium chloride; UDP-glucosyltransferase UGTSL / aq. phosphate buffer / 1 h / 30 °C / pH 7.2 / Enzymatic reaction 2: magnesium chloride; UDP-glucosyltransferase UGT76G1 / aq. phosphate buffer / 30 °C / pH 7.2 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: magnesium chloride; UGT91D2 / aq. phosphate buffer / 1 h / 30 °C 2: magnesium chloride; UGT76G1 / aq. phosphate buffer / 30 °C View Scheme

: 133-89-1
UDP-glucose

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium chloride; UDP-glucosyltransferase UGTSL / aq. phosphate buffer / 1 h / 30 °C / pH 7.2 / Enzymatic reaction 2: magnesium chloride; UDP-glucosyltransferase UGT76G1 / aq. phosphate buffer / 30 °C / pH 7.2 / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: magnesium chloride; UGT91D2 / aq. phosphate buffer / 1 h / 30 °C 2: magnesium chloride; UGT76G1 / aq. phosphate buffer / 30 °C View Scheme

: 133-89-1
UDP-glucose

: 57817-89-7
stevioside

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
With UDP-glucosyltransferase UGT76G1; magnesium chloride In aq. phosphate buffer at 30℃; pH=7.2; Catalytic behavior; Kinetics; Enzymatic reaction; chemoselective reaction;
With UGT76G1; magnesium chloride In aq. phosphate buffer at 30℃;

: 952585-00-1
uridine-5'-diphosphoglucose

: 57817-89-7
stevioside

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
With UDP-glucosyltransferase from Stevia rebaudiana, recombinant; magnesium chloride In aq. phosphate buffer at 30℃; for 1h; pH=7.2; Time; Enzymatic reaction;

: 57817-89-7
stevioside

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
With β-1,3-glucanase from Irpex lacteus In aq. buffer at 55℃; for 3h; pH=4.5; Enzymatic reaction;	150 mg

: 57-50-1
Sucrose

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sucrose synthase / Enzymatic reaction 2: magnesium chloride; UGT76G1 / aq. phosphate buffer / 30 °C View Scheme
Multi-step reaction with 3 steps 1: sucrose synthase / Enzymatic reaction 2: magnesium chloride; UGT91D2 / aq. phosphate buffer / 1 h / 30 °C 3: magnesium chloride; UGT76G1 / aq. phosphate buffer / 30 °C View Scheme

: 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid [(2-O-β-D-glucopyranosyl-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester]

A: 13-[(2-O-β-D-glucopyranosyI-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid [(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester]

B: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
With naringinase In aq. acetate buffer at 30℃; for 3.3h; Enzymatic reaction;

: (13-[((2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl)-β-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid-(3-O-β-D-glucopyranosyl)-β-D-glucopyranosyl) ester

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
With isolase In aq. acetate buffer at 30℃; for 18h; Enzymatic reaction;

: 13-O-[2,3-di-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,6-O-benzylidene-β-D-glucopyranosyl]steviol (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) ester

: 58543-16-1
rebaudioside A

Conditions

Conditions	Yield
Stage #1: 13-O-[2,3-di-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-4,6-O-benzylidene-β-D-glucopyranosyl]steviol (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) ester With toluene-4-sulfonic acid In methanol; dichloromethane at 20℃; Stage #2: With sodium methylate In methanol at 20℃; for 6h;	34 mg

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Specification

The 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)-, with the CAS registry number 58543-16-1, is also known as Rebaudioside A. It belongs to the product category of Miscellaneous Natural Products. This chemical's molecular formula is C₄₄H₇₀O₂₃ and molecular weight is 967.01. Its systematic name is called 1-O-[(5β,9β,10α)-12-{[β-D-glucopyranosyl-(1->2)-[β-D-glucopyranosyl-(1->3)]-(3ξ)-β-D-ribo-hexopyranosyl]oxy}-18-oxokaur-16-en-18-yl]-D-glucopyranose. This chemical's classification code is Sweetening Agents. It should be stored in a sealed container which should be stored in a dry, cool place.

Physical properties of 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)-: (1)ACD/LogP: -1.12; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -1.12; (4)ACD/LogD (pH 7.4): -1.12; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 5.84; (8)ACD/KOC (pH 7.4): 5.84; (9)#H bond acceptors: 23; (10)#H bond donors: 14; (11)#Freely Rotating Bonds: 27; (12)Index of Refraction: 1.657; (13)Molar Refractivity: 224.03 cm³; (14)Molar Volume: 608.5 cm³; (15)Surface Tension: 92.7 dyne/cm; (16)Density: 1.58 g/cm³; (17)Flash Point: 320.2 °C; (18)Enthalpy of Vaporization: 183.36 kJ/mol; (19)Boiling Point: 1103.5 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)[C@]7(C)CCC[C@@]6(C)[C@@H]8CC(O[C@@H]4O[C@H](CO)[C@@H](O)C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]4O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C5C(=C )\CC8(C5)CC[C@@H]67
(2)InChI: InChI=1/C44H70O23/c1-16-10-44-8-5-23-42(2,6-4-7-43(23,3)41(59)67-39-34(58)31(55)27(51)21(14-47)63-39)24(44)9-18(17(16)11-44)60-40-36(66-38-33(57)30(54)26(50)20(13-46)62-38)35(28(52)22(15-48)64-40)65-37-32(56)29(53)25(49)19(12-45)61-37/h17-40,45-58H,1,4-15H2,2-3H3/t17?,18?,19-,20-,21-,22-,23+,24+,25-,26-,27-,28-,29+,30+,31+,32-,33-,34-,35?,36-,37+,38+,39?,40-,42-,43-,44?/m1/s1
(3)InChIKey: CHSPVGNDBQFQNR-VECHAMHWBM

58543-16-1

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Specification