Eugenin

Base Information

• Chemical Name: Eugenin
• CAS No.: 480-34-2
• Molecular Formula: C11H10O4
• Molecular Weight: 206.198
• UNII: E8D279U89S
• DSSTox Substance ID: DTXSID80197381
• Nikkaji Number: J12.704C
• Wikipedia: Eugenin
• Wikidata: Q5408256
• Metabolomics Workbench ID: 47424
• ChEMBL ID: CHEMBL446974
• Mol file: 480-34-2.mol

Synonyms:Eugenin;480-34-2;5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one;5-HYDROXY-7-METHOXY-2-METHYLCHROMONE;5-hydroxy-7-methoxy-2-methylchromen-4-one;5-Hydroxy-7-methoxy-2-methyl-4H-1-benzopyran-4-one;5-Hydroxy-7-methoxy-2-methylchrone;4H-1-Benzopyran-4-one, 5-hydroxy-7-methoxy-2-methyl-;CHEMBL446974;CHEBI:67374;E8D279U89S;Chromone, 5-hydroxy-7-methoxy-2-methyl-;UNII-E8D279U89S;SCHEMBL1860860;DTXSID80197381;CS-D0395;BDBM50338662;MFCD03001454;2-Methyl-5-hydroxy-7-methoxychromone;AKOS022506034;5-Hydroxy-7-methoxy-2-methyl-Chromone;AS-30953;HY-33351;2-METHYL-7-METHOXY-5-HYDROXYCHROMONE;C20210;5-Hydroxy-7-methoxy-2-methyl-4H-chromen-4-one #;Q5408256

Chemical Property of Eugenin

Chemical Property:

• Vapor Pressure: 1.29E-06mmHg at 25°C
• Melting Point: 118-119 °C(Solv: ethanol (64-17-5))
• Boiling Point: 389.2°C at 760 mmHg
• PKA: 6.42±0.40(Predicted)
• Flash Point: 157.2°C
• PSA: 59.67000
• Density: 1.309g/cm³
• LogP: 1.81560
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 206.05790880
• Heavy Atom Count: 15
• Complexity: 297

Purity/Quality:

NLT 98% ^*data from raw suppliers

Eugenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(C=C(C=C2O1)OC)O
• Uses: Eugenin can be used for new phytoconstituents, anti-?microbial and cytotoxic activities.

Technology Process of Eugenin

There total 7 articles about Eugenin 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%

eugenin (1013-69-0) + dimethyl sulfate (77-78-1) → eugenin (480-34-2)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 12h;

DOI:10.1021/ol303482k

Reference yield:

5-hydroxy-2-methylchromone-7-O-rutinoside → β-D-glucose (492-61-5) + eugenin (480-34-2) + β-L-rhamnose (6155-36-8)

Guidance literature:

With naringinase from Penicillium decumbens; Enzymatic reaction;

DOI:10.1021/np8006342

Reference yield:

2-(ethoxymethyl)-5, 7-dimethoxy-4H-chromen-4-one (26213-83-2) → eugenin (480-34-2)

Guidance literature:

With hydrogen iodide; acetic anhydride; at 115 ℃;

upstream raw materials:

diazomethane

eugenin

dimethyl sulfate

methyl iodide

Downstream raw materials:

eugenin

2,6-dihydroxy-4-methoxy-acetophenone

2,4,6-trihydroxytoluene

C₂₂H₂₄O₅

Refernces

• 1、 Kim, U Bin,Furkert, Daniel P.,Brimble, Margaret A.. "Total synthesis of chaetoquadrins A-C". supporting information. p. 658 - 661. Retrieved 2013/04/10.