Aucuparin

Base Information

• Chemical Name: Aucuparin
• CAS No.: 3687-28-3
• Molecular Formula: C14H14O3
• Molecular Weight: 230.263
• UNII: 18IC7401L0
• DSSTox Substance ID: DTXSID40190353
• Nikkaji Number: J346.811I
• Wikidata: Q27105881
• Metabolomics Workbench ID: 69343
• ChEMBL ID: CHEMBL1079777
• Mol file: 3687-28-3.mol

Synonyms:(1,1'-biphenyl)-4-ol,3,5-dimethoxy-;3,5-dimethoxy(1,1'-biphenyl)-4-ol;aucuparin

Chemical Property of Aucuparin

Chemical Property:

• Vapor Pressure: 2.34E-05mmHg at 25°C
• Boiling Point: 349.4°C at 760 mmHg
• Flash Point: 165.1°C
• Density: 1.144g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 212

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1O)OC)C2=CC=CC=C2

Technology Process of Aucuparin

There total 14 articles about Aucuparin 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: 98.0%

4-(benzyloxy)-3,5-dimethoxy-1,1'-biphenyl → aucuparin (3687-28-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h;

DOI:10.1002/ejoc.201501009

Reference yield: 82.0%

5-phenyl-1,2,3-trimethoxybenzene (50816-75-6) → aucuparin (3687-28-3)

Guidance literature:

With magnesium iodide; at 80 ℃; for 4h;

DOI:10.1055/s-0034-1379987

Reference yield: 75.0%

4-bromo-2,6-dimethoxyphenol (70654-71-6) + phenylboronic acid (98-80-6) → aucuparin (3687-28-3)

Guidance literature:

With palladium 10% on activated carbon; potassium hydroxide; at 150 ℃; for 0.5h; Reagent/catalyst; Microwave irradiation; Inert atmosphere;

DOI:10.1021/jo500675a

upstream raw materials:

3,5-dimethoxybiphenyl

5-phenyl-cyclohexane-1,3-dione

5-phenylresorcinol

5-phenyl-1,2,3-trimethoxybenzene

Downstream raw materials:

3,4,5-Trihydroxy-biphenyl

Refernces

Suzuki-Miyaura coupling of halophenols and phenol boronic acids: Systematic investigation of positional isomer effects and conclusions for the synthesis of phytoalexins from pyrinae

10.1021/jo500675a

The research investigates the Suzuki?Miyaura coupling reactions of various halophenols (o-, m-, and p-iodophenols and bromophenols) with phenol boronic acids under standardized conditions using Pd/C as a catalyst and water as a solvent. The study aims to systematically explore the effects of positional isomerism on the reactivity and yield of biphenol products, with a particular focus on synthesizing phytoalexins from the subtribe Pyrinae, which have antibacterial properties and are produced by fruit trees in response to microbial infections. The researchers found that certain combinations, such as those leading to 2,4′-biphenol, were particularly challenging but could be improved by using additives like fluorides. The study concluded that microwave irradiation significantly enhanced the efficiency of the coupling reactions, especially for bromophenols, and provided optimized protocols for synthesizing various phytoalexins, including aucuparin, rhaphiolepsin, and garcibiphenyl C, with synthetically useful yields.

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