(E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Base Information

• Chemical Name: (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS No.: 220430-82-0
• Molecular Formula: C16H14 O4
• Molecular Weight: 270.285
• European Community (EC) Number: 681-911-6
• ChEMBL ID: CHEMBL130640
• Metabolomics Workbench ID: 73701
• Nikkaji Number: J566.620A
• Wikidata: Q106892465
• Mol file: 220430-82-0.mol

Synonyms:220430-82-0;2',4-Dihydroxy-3-methoxychalcone;(E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one;CHEMBL130640;(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one;4,2'-DIHYDROXY-3-METHOXYCHALCONE;3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one;SCHEMBL3396591;NGQQEEYHKPKSER-SOFGYWHQSA-N;2',4-dihydroxy-3-methoxy-chalcone;BDBM50042983;MFCD03788903;NSC 94615;AKOS027320151;AS-72458;CS-0359545;4,2'-Dihydroxy-3-methoxychalcone, AldrichCPR;AG-690/15427086;3-(4-Hydroxy-3-methoxy-phenyl)-1-(2-hydroxy-phenyl)-propenone;3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)-2-propen-1-one;2-Propen-1-one, 3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)-

Chemical Property of (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Chemical Property:

• Melting Point: 127-129°C
• PSA: 66.76000
• LogP: 3.00250
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 352

Purity/Quality:

99% ^*data from raw suppliers

2'',4-Dihydroxy-3-methoxychalcone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C=CC(=O)C2=CC=CC=C2O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)/C=C/C(=O)C2=CC=CC=C2O)O

Technology Process of (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

There total 9 articles about (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 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: 73.4%

C18H18O5 → (E)-1-(2,4-dihydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one (220430-82-0)

Guidance literature:

With hydrogenchloride; In methanol; water; Reflux;

DOI:10.1016/j.ejmech.2019.01.039

Reference yield: 67.0%

2',4'-dihydroxy-4-acetophenone (89-84-9) + 3-methoxy-benzaldehyde (591-31-1) → (E)-1-(2,4-dihydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one (220430-82-0)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃;

DOI:10.1016/j.bmc.2011.10.074

Reference yield:

2',4'-dihydroxy-4-acetophenone (89-84-9) → (E)-1-(2,4-dihydroxyphenyl)-3-(3-methoxyphenyl)prop-2-en-1-one (220430-82-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium p-toluene sulfonate / CH₂Cl₂ / 25 °C

2: Ba(OH)2*8H₂O / ethanol / 24 h / 30 °C

3: aq. HCl / ethanol / 25 °C

With hydrogenchloride; barium dihydroxide; pyridinium p-toluenesulfonate; In ethanol; dichloromethane; 2: Claisen-Schmidt condensation;

DOI:10.1016/j.bmcl.2005.05.067

upstream raw materials:

(E)-1-[2-Hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(3-methoxy-phenyl)-propenone

2',4'-dihydroxy-4-acetophenone

2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone

3-methoxy-benzaldehyde

Downstream raw materials:

3'-methoxy-7-hydroxyflavanone

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