[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9R,10S,13R)-13-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Base Information

• Chemical Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9R,10S,13R)-13-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS No.: 57817-89-7
• Molecular Formula: C38H60O18
• Molecular Weight: 804.884
• Hs Code.: 29389090
• European Community (EC) Number: 260-975-5
• Wikipedia: Stevioside
• RXCUI: 37106
• Mol file: 57817-89-7.mol

Synonyms:steviol glycoside;stevioside

Chemical Property of [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9R,10S,13R)-13-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 198 °C
• Refractive Index: -39.3 ° (C=6, H2O)
• Boiling Point: 963.3 °C at 760 mmHg
• PKA: 12.51±0.70(Predicted)
• Flash Point: 290.3 °C
• PSA: 294.98000
• Density: 1.53 g/cm³
• LogP: -2.93810
• Storage Temp.: 0-6°C
• Solubility.: DMSO: soluble25mg/mL, clear
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 10
• Exact Mass: 804.37796506
• Heavy Atom Count: 56
• Complexity: 1450

Purity/Quality:

40%-98% ^*data from raw suppliers

Stevioside hydrate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)(C)C(=O)OC7C(C(C(C(O7)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)O[C@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)(C)C(=O)O[C@@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• Recent ClinicalTrials: Oral Changes With Caloric and no Caloric Sweeteners
• Recent EU Clinical Trials: Intervention studier med steviol til belysning af dosis respons forhold samt langtidseffekt hos personer med type 2 diabetes
• Production method: Asteraceae small shrub sweet daisy (Stevia rebaudiana Bertoni) leaves which are from Paraguay of northeast America ,dry them , extract them using ethanol , the extract is added ether to precipitate the sweet substance , and then recrystallize them from methanol. In terms of dry leaves, yield is about 6%. Our Jiangsu, Fujian, Xinjiang and other places have large-scale cultivation of stevia.
• Uses: Stevioside is a glycoside from the stevia plant. Stevioside is a natural sweetening agent with sweetness about 250 times that of sugar with negligible effect on blood glucose. Stevioside, much like other steviol glycoside is known for its application in treatment of many diseases like diabetes and high blood pressure. It is also used as a food additive. Stevioside is a glycoside from the stevia plant. Stevioside is a natural sweetening agent with sweetness about 250 times that of sugar with negligible effect on blood glucose. Stevioside, much like ot her steviol glycoside is known for its application in treatment of many diseases like diabetes and high blood pressure. It is also used as a food additive and in dietary supplements. Stevioside is a natural, calorie-free sweetener obtained from the leaves of the plant stevia rebaudiana bertoni. it is a steviol glycoside in which steviol’s carboxyl and hydroxyl hydrogen atom is replaced with glu- cose; it has two linked glucose molecules at the hydroxyl site. it is the major steviol glycoside found in the stevia plant and is 250–300 times sweeter than sugar. it is heat and ph stable. it has been associ- ated with a bitter and licorice taste. see steviol glycoside.

Technology Process of [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9R,10S,13R)-13-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

There total 10 articles about [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4S,5R,9R,10S,13R)-13-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate 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: 90.6%

→ stevioside (57817-89-7)

Guidance literature:

Reference yield: 31.1%

13-O-β-D-glucopyranosyl-19-O-β-D-glucopyranosylsteviol (64849-39-4,104873-42-9) + uridine-5'-diphosphoglucose (952585-00-1) → C38H60O18 + stevioside (57817-89-7)

Guidance literature:

With glycosyltransferase YjiC from Bacillus licheniformis; In aq. buffer; regioselective reaction; Enzymatic reaction;

DOI:10.1021/acs.jafc.0c03236

Reference yield:

UDP-glucose (133-89-1) + 13-O-β-D-glucopyranosyl-19-O-β-D-glucopyranosylsteviol (64849-39-4,104873-42-9) → stevioside (57817-89-7)

Guidance literature:

With UDP-glucosyltransferase UGTSL; magnesium chloride; In aq. phosphate buffer; at 30 ℃; for 1h; pH=7.2; chemoselective reaction; Catalytic behavior; Enzymatic reaction;

upstream raw materials:

C₆₀H₈₂O₂₉

13-O-[3,4,6-tri-O-acetyl-β-D-glucopyranosyl(1-2α')-3',4',6'-tri-O-acetyl-β-D-glucopyranosyl]ent-caur-16-en-19-oic acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

UDP-glucose

Downstream raw materials:

isosteviol

C₃₇H₅₈O₁₉

rebaudioside D

rebaudioside A

Refernces

• 1、 -. "RECOMBINANT PRODUCTION OF STEVIOL GLYCOSIDES". Paragraph 0054; 0333; 0334; 0360; 0361. . Retrieved 2016/08/17.
• 2、 -. "PRODUCTION OF STEVIOL GLYCOSIDES IN RECOMBINANT HOSTS". Paragraph 00196. . Retrieved 2016/08/23.