Mesuol

Base Information

• Chemical Name: Mesuol
• CAS No.: 16981-20-7
• Molecular Formula: C24H24 O5
• Molecular Weight: 392.452
• Hs Code.: 2932209090
• ChEMBL ID: CHEMBL197069
• DSSTox Substance ID: DTXSID50168760
• Metabolomics Workbench ID: 23022
• Nikkaji Number: J15.280C
• NSC Number: 130114
• Wikidata: Q83038382
• Mol file: 16981-20-7.mol

Synonyms:4-phenylcoumarin;mesuol

Chemical Property of Mesuol

Chemical Property:

• Vapor Pressure: 5.49E-15mmHg at 25°C
• Melting Point: 171℃
• Boiling Point: 599.9°C at 760 mmHg
• Flash Point: 206.8°C
• PSA: 87.74000
• Density: 1.238g/cm³
• LogP: 5.21860
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 392.16237386
• Heavy Atom Count: 29
• Complexity: 681

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=O)C1=C(C2=C(C(=C1O)CC=C(C)C)OC(=O)C=C2C3=CC=CC=C3)O
• Description: Mesuol is a coumarin isolated from the stem bark of Mesua borneensis, which displays antimalarial and antioxidant activities. Mesuol was shown to inhibit HIV-1 replication by targeting the NF-kappaB pathway.

Technology Process of Mesuol

There total 6 articles about Mesuol 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: 20.0%

5,7-dihydroxy-6-(2-methylpropionyl)-4-phenylcoumarin (98192-59-7) + 3,3-dimethyl-allyl chloride (503-60-6) → 5,7-dihydroxy-6-isobutyryl-8-(3-methylbut-2-enyl)-4-phenyl-2H-chromen-2-one (16981-20-7)

Guidance literature:

With potassium hydroxide; at 0 ℃; for 1.5h;

Reference yield:

5,7-dihydroxy-6-(2-methylpropionyl)-4-phenylcoumarin (98192-66-6) + prenyl bromide (870-63-3) → 5,7-dihydroxy-6-isobutyryl-8-(3-methylbut-2-enyl)-4-phenyl-2H-chromen-2-one (16981-20-7)

Guidance literature:

With potassium hydroxide; In water; at 0 ℃;

DOI:10.1016/S0040-4039(00)98874-9

Reference yield:

3,5-dihydroxyphenol (108-73-6) → 5,7-dihydroxy-6-isobutyryl-8-(3-methylbut-2-enyl)-4-phenyl-2H-chromen-2-one (16981-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / AlCl₃ / CS₂; nitrobenzene / 0.5 h / Heating

2: cc. H₂SO₄ / acetic acid / 480 h / Ambient temperature

3: 20 percent / 10percent aq. potassium hydroxide / 1.5 h / 0 °C

With potassium hydroxide; aluminium trichloride; sulfuric acid; In carbon disulfide; acetic acid; nitrobenzene;

upstream raw materials:

5,7-dihydroxy-6-(2-methylpropionyl)-4-phenylcoumarin

prenyl bromide

5,7-dihydroxy-6-(2-methylpropionyl)-4-phenylcoumarin

3,3-dimethyl-allyl chloride

Downstream raw materials:

5-hydroxy-6-isobutyryl-8,8-dimethyl-4-phenyl-2H,8H-pyrano[2,3-h]chromen-2-one

5,7-dihydroxy-6-(3-methylbut-2-enyl)-8-(2-methylpropanoyl)-4-phenylbenzopyran-2(2H)-one

Refernces

• 1、 Crombie,Jones,Palmer. "Synthesis of mammeins and surangin A". . p. 2929 - 2932. Retrieved 2007/10/02.