Tremuloidin

Base Information

• Chemical Name: Tremuloidin
• CAS No.: 529-66-8
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.39
• UNII: F2UU914Q2B
• DSSTox Substance ID: DTXSID00967366
• Wikidata: Q27277555
• Metabolomics Workbench ID: 141486
• ChEMBL ID: CHEMBL516994
• Mol file: 529-66-8.mol

Synonyms:Tremuloidin;529-66-8;tremuldin;UNII-F2UU914Q2B;F2UU914Q2B;[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(hydroxymethyl)phenoxy]oxan-3-yl] benzoate;beta-D-Glucopyranoside, 2-(hydroxymethyl)phenyl, 2-benzoate;2'-benzoylsalicin;2'-O-benzoylsalicin;SALICIN 2-BENZOATE;CHEMBL516994;SCHEMBL1055081;DTXSID00967366;CHEBI:155892;2-(Hydroxymethyl)phenyl 2-O-benzoylhexopyranoside;Q27277555;2-(hydroxymethyl)phenyl 2-O-benzoyl-beta-D-glucopyranoside;.BETA.-D-GLUCOPYRANOSIDE, 2-(HYDROXYMETHYL)PHENYL, 2-BENZOATE;(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(2-(hydroxymethyl)phenoxy)tetrahydro-2H-pyran-3-yl benzoate

Chemical Property of Tremuloidin

Chemical Property:

• Vapor Pressure: 1.15E-16mmHg at 25°C
• Boiling Point: 628.5°Cat760mmHg
• Flash Point: 223.5°C
• PSA: 125.68000
• Density: 1.44g/cm³
• LogP: 0.22230
• XLogP3: 1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 390.13146766
• Heavy Atom Count: 28
• Complexity: 495

Purity/Quality:

98%Min ^*data from raw suppliers

Tremuloidin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OC2C(C(C(OC2OC3=CC=CC=C3CO)CO)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC=CC=C3CO)CO)O)O
• Uses: Tremuloidin (cas# 529-66-8) is a phenolic compound found in Salix alba (medicinal plant), which was investigated on its genotoxic on human cells.

Technology Process of Tremuloidin

There total 5 articles about Tremuloidin 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: 90.0%

2'-O-Benzoyl-4',6'-O-benzylidene-7-trityloxy-o-tolyl-β-D-glucopyranoside (144364-13-6) → tremuloidine (529-66-8)

Guidance literature:

With acetic acid; 1) 1h, 40 deg C, 2) 6-8h, r.t.;

DOI:10.1016/0031-9422(92)83663-J

Reference yield:

benzoyl cyanide (613-90-1) → tremuloidine (529-66-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 35 percent / Et₃N / acetonitrile / 0.5 h

2: 90 percent / 80percent AcOH / 1) 1h, 40 deg C, 2) 6-8h, r.t.

With acetic acid; triethylamine; In acetonitrile;

DOI:10.1016/0031-9422(92)83663-J

Reference yield:

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside (144364-11-4) → tremuloidine (529-66-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / 4A molecular sieves, pyridine / CH₂Cl₂ / 10 h / Ambient temperature

2: 35 percent / Et₃N / acetonitrile / 0.5 h

3: 90 percent / 80percent AcOH / 1) 1h, 40 deg C, 2) 6-8h, r.t.

With pyridine; 4 A molecular sieve; acetic acid; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/0031-9422(92)83663-J

upstream raw materials:

2'-O-Benzoyl-4',6'-O-benzylidene-7-trityloxy-o-tolyl-β-D-glucopyranoside

benzoyl cyanide

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside

4',6'-O-Benzylidene-7-trityloxy-o-tolyl-β-D-glucopyranoside