2-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-phenethylbenzoic acid

Base Information

• Chemical Name: 2-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-phenethylbenzoic acid
• CAS No.: 80489-90-3
• Molecular Formula: C21H24O4
• Molecular Weight: 340.419
• Hs Code.: 2918990090
• ChEMBL ID: CHEMBL491820
• DSSTox Substance ID: DTXSID00591701
• Metabolomics Workbench ID: 138939
• Nikkaji Number: J530.381H
• Wikidata: Q27467733
• Mol file: 80489-90-3.mol

Synonyms:amorfrutin A

Chemical Property of 2-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-phenethylbenzoic acid

Chemical Property:

• Boiling Point: 473.992 °C at 760 mmHg
• Flash Point: 161.575 °C
• PSA: 66.76000
• Density: 1.159 g/cm³
• LogP: 4.39290
• Storage Temp.: 2-8°C
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 340.16745924
• Heavy Atom Count: 25
• Complexity: 449

Purity/Quality:

≥97% ^*data from raw suppliers

Amorfrutin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C=C(C(=C1O)C(=O)O)CCC2=CC=CC=C2)OC)C
• Uses: Amorfrutin is a natural product isolated from A. fruticosa. Amorfrutin exhibits antidiabetic properties. Amorfrutin binds to and activate PPARγ, which results in selective gene expression involved with lipid and glucose metabolism.

Technology Process of 2-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-phenethylbenzoic acid

There total 38 articles about 2-Hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-phenethylbenzoic acid 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: 99.0%

7-methoxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-5-phenethyl-4H-benzo[d][1,3]dioxin-4-one (1353896-19-1) → 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid (80489-90-3)

Guidance literature:

With potassium hydroxide; In water; dimethyl sulfoxide; at 80 ℃; for 18h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.202100301

Reference yield: 95.0%

ethyl 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoate (1431610-36-4) → 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid (80489-90-3)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 2.5h; Reflux;

DOI:10.1021/acs.joc.0c03043

Reference yield: 92.0%

methyl 2-hydroxy-4-methoxy-3-(3-methyl-2-buten-1-yl)-6-(2-phenylethyl)benzoate → 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoic acid (80489-90-3)

Guidance literature:

With water; potassium hydroxide; In ethanol; for 2h; Reflux;

DOI:10.1021/acs.jmedchem.6b01301

upstream raw materials:

7-methoxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-5-phenethyl-4H-benzo[d][1,3]dioxin-4-one

ethyl 2-hydroxy-4-methoxy-6-(2-phenylethyl)-benzoate

2,4-dihydroxy-6-phenethyl-benzoic acid ethyl ester

ethyl 2-hydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)-6-(2-phenylethyl)benzoate