16981-20-7

Basic information

• Product Name: 5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methylpropanoyl)-4-phenyl-2H-1-benzopyran-2-one
• Synonyms: 5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-4-phenyl-2H-1-benzopyran-2-one;5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methylpropanoyl)-4-phenyl-2H-1-benzopyran-2-one;Mesuol;5,7-Dihydroxy-6-isobutyryl-8-(3-methyl-2-butenyl)-4-phenylcoumarin
• CAS NO: 16981-20-7
• Molecular Formula: C₂₄H₂₄O₅
• Molecular Weight: 392.44
• Mol File: 16981-20-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 171℃
• Boiling Point: 599.9°C at 760 mmHg
• Flash Point: 206.8°C
• Appearance: /
• Density: 1.238g/cm³
• Vapor Pressure: 5.49E-15mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methylpropanoyl)-4-phenyl-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methylpropanoyl)-4-phenyl-2H-1-benzopyran-2-one(16981-20-7)
• EPA Substance Registry System: 5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(2-methylpropanoyl)-4-phenyl-2H-1-benzopyran-2-one(16981-20-7)

Safety Data

• Hazardous Substances Data: 16981-20-7(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C24H24O5/c1-13(2)10-11-16-22(27)20(21(26)14(3)4)23(28)19-17(12-18(25)29-24(16)19)15-8-6-5-7-9-15/h5-10,12,14,27-28H,11H2,1-4H3

Upstream product

• 98-86-2 acetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 98192-59-7 5,7-dihydroxy-6-(2-methylpropionyl)-4-phenylcoumarin 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 98192-66-6 5,7-dihydroxy-6-(2-methylpropionyl)-4-phenylcoumarin 
• 870-63-3 prenyl bromide 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 35458-21-0 phlorisobutyrophenone 

Downstream Products

• 21721-08-4 5-hydroxy-6-isobutyryl-8,8-dimethyl-4-phenyl-2H,8H-pyrano[2,3-h]chromen-2-one 
• 16981-21-8 5,7-dihydroxy-6-(3-methylbut-2-enyl)-8-(2-methylpropanoyl)-4-phenylbenzopyran-2(2H)-one 

Relevant articles and documents

Synthesis of Mammea Coumarins. Part 1. The Coumarins of the Mammea A, B, and C Series

The naturally-occuring Mammea coumarins of the 4-phenyl-(mammea A), propyl-(mammea B), and 4-pentyl-(mammea C) series have been prepared by Pechmann condensation of an acylphloroglucinol (3-methylbutyryl-, 2-methylbutyryl-, butyryl-, or 2-methylpropionyl-) with the appropriate β-ketoester to give a mixture of 6- and 8-acyl-5,7-dihydroxycoumarins that could be separated.C-Alkylation with 3-methylbut-2-enyl bromide, or 3,7-dimethylocta-2,6-dienyl chloride, in aqueous potassium hydroxide completed the synthesis of the Mammea coumarins having unmodified prenyl or geranyl substituents; oxidative modification of the prenyl group led to the mammea cyclo E and cyclo F coumarins.Some mammea cyclo D (chromeno) coumarins were synthesized by reaction of acylcoumarins with 1,1-dimethoxy-3-methylbutan-3-ol.