Ethyl vanillin beta-D-glucopyranoside

Base Information

• Chemical Name: Ethyl vanillin beta-D-glucopyranoside
• CAS No.: 122397-96-0
• Molecular Formula: C15H20 O8
• Molecular Weight: 328.319
• European Community (EC) Number: 602-769-3
• UNII: 24XJ91ONU1
• DSSTox Substance ID: DTXSID50153590
• Nikkaji Number: J1.544.202F
• Wikidata: Q27253884
• Mol file: 122397-96-0.mol

Synonyms:122397-96-0;Ethyl vanillin beta-D-glucopyranoside;Ethyl vanillin glucoside;Glucoethylvanillin;UNII-24XJ91ONU1;24XJ91ONU1;2-Ethoxy-4-formylphenyl beta-D-glucopyranoside;ETHYLVANILLINBETA-D-GLUCOPYRANOSIDE;EC 602-769-3;3-Ethoxy-4-(beta-D-glucopyranosyloxy)benzaldehyde;Benzaldehyde, 3-ethoxy-4-(beta-D-glucopyranosyloxy)-;3-ethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde;SCHEMBL2949239;FEMA NO. 3801;DTXSID50153590;AC-32346;4-(-D-Glucopyranosyloxy)-3-Ethoxybenzaldehyde;ETHYL VANILLIN .BETA.-D-GLUCOPYRANOSIDE;ETHYL VANILLIN .BETA.-D-GLUCOPYRANOSIDE [FHFI];Q27253884;2-ETHOXY-4-FORMYLPHENYL .BETA.-D-GLUCOPYRANOSIDE;BENZALDEHYDE, 3-ETHOXY-4-(.BETA.-D-GLUCOPYRANOSYLOXY)-

Chemical Property of Ethyl vanillin beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 6.15E-15mmHg at 25°C
• Boiling Point: 593.6°Cat760mmHg
• Flash Point: 213.4°C
• PSA: 125.68000
• Density: g/cm³
• LogP: -0.92350
• Water Solubility.: 1g/L at 20℃
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 328.11581759
• Heavy Atom Count: 23
• Complexity: 379

Purity/Quality:

99.9% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=CC(=C1)C=O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: CCOC1=C(C=CC(=C1)C=O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of Ethyl vanillin beta-D-glucopyranoside

There total 5 articles about Ethyl vanillin beta-D-glucopyranoside 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: 93.0%

(4-formyl-2-ethoxyphenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (121358-45-0) → (4-formyl-2-ethoxyphenyl) β-D-glucopyranoside (122397-96-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.25h;

DOI:10.1081/CAR-120019010

Reference yield:

4-hydroxy-3-ethoxybenzaldehyde (121-32-4) → (4-formyl-2-ethoxyphenyl) β-D-glucopyranoside (122397-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / tetrabutylammonium bromide; aqueous sodium hydroxide / CH₂Cl₂ / 0.75 h / 20 °C

2: 93 percent / sodium methoxide / methanol / 0.25 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; sodium methylate; In methanol; dichloromethane; 2: Zemplen deacetylation;

DOI:10.1081/CAR-120019010

Reference yield:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) → (4-formyl-2-ethoxyphenyl) β-D-glucopyranoside (122397-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 46 percent / molecular sieves 4 Angstroem; BF₃*Et₂O / CH₂Cl₂ / 2 h / -18 °C

2: 93 percent / sodium methoxide / methanol / 0.25 h / 20 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; 2: Zemplen deacetylation;

DOI:10.1081/CAR-120019010

upstream raw materials:

(4-formyl-2-ethoxyphenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

4-hydroxy-3-ethoxybenzaldehyde

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

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

Refernces

• 1、 Simonsen, Henrik Toft,Nielsen, Mette S.,Christensen, Niels J.,Christensen, Ulla,Cour, Thomas V. La,Motawia, Mohammed Saddik,Jespersen, Birthe P.M.,Engelsen, Soren B.,Moller, Birger Lindberg. "Molecular interactions between Barley and Oat β-glucans and phenolic derivatives". experimental part. p. 2056 - 2064. Retrieved 2010/07/02.