Rebaudioside A

Base Information

• Chemical Name: Rebaudioside A
• CAS No.: 58543-16-1
• Deprecated CAS: 60129-62-6,64859-60-5,65455-42-7
• Molecular Formula: C44H70O23
• Molecular Weight: 967.026
• Hs Code.: 29389090
• European Community (EC) Number: 611-696-6
• UNII: B3FUD0528F
• DSSTox Substance ID: DTXSID8047898
• Nikkaji Number: J13.835E
• Wikipedia: Rebaudioside_A
• Wikidata: Q427000
• RXCUI: 1667222
• Metabolomics Workbench ID: 143736
• Mol file: 58543-16-1.mol

Synonyms:19-O-beta-glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosyl-13-hydroxykaur-16-en-19-oic acid;19-O-beta-glucopyranosyl-13-O-(beta-glucopyranosyl(1-2)-beta-glucopyranosyl(1-3))-beta-glucopyranosylsteviol;rebaudioside A

Chemical Property of Rebaudioside A

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 242-244 °C
• Refractive Index: 1.657
• Boiling Point: 1103.5 °C at 760 mmHg
• PKA: 12.51±0.70(Predicted)
• Flash Point: 320.2 °C
• PSA: 374.13000
• Density: 1.58 g/cm³
• LogP: -5.11390
• Storage Temp.: room temp
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Sparingly)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 23
• Rotatable Bond Count: 13
• Exact Mass: 966.43078848
• Heavy Atom Count: 67
• Complexity: 1760

Purity/Quality:

99% ^*data from raw suppliers

Rebaudioside A ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)OC6C(C(C(C(O6)CO)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)(C)C(=O)OC8C(C(C(C(O8)CO)O)O)O
• Isomeric SMILES: C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@](C3)(C(=C)C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)(C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• Recent ClinicalTrials: Microbiome and Non-caloric Sweeteners in Humans
• 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.
• 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. natural sweetener to diabetics and others on carbohydrate-controlled diets 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.

Technology Process of Rebaudioside A

There total 10 articles about Rebaudioside A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

stevioside (57817-89-7) + Sucrose (57-50-1) → rebaudioside A (58543-16-1)

Guidance literature:

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;

DOI:10.1080/09168451.2015.1072457

Reference yield:

stevioside (57817-89-7) → rebaudioside A (58543-16-1)

Guidance literature:

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

DOI:10.1016/j.phytochem.2016.03.004

Reference yield:

(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 → rebaudioside A (58543-16-1)

Guidance literature:

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

upstream raw materials:

13-O-β-D-glucopyranosyl-19-O-β-D-glucopyranosylsteviol

UDP-glucose

stevioside

uridine-5'-diphosphoglucose

Downstream raw materials:

rebaudioside D

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)-3-O-(β-D-glucopyranosyl)-β-D-glucopyranosyl ester

isosteviol

steviol

Refernces

• 1、 Singla, Ramit,Jaitak, Vikas. "Synthesis of rebaudioside A from stevioside and their interaction model with hTAS2R4 bitter taste receptor". . p. 106 - 111. Retrieved 2016.
• 2、 -. "HIGH-PURITY STEVIOL GLYCOSIDES". . . Retrieved 2016/04/09.