4139-73-5

Basic information

• Product Name: 4-hydroxy-3-propionyl-2H-chromen-2-one
• Synonyms: Aids129957;Aids-129957;Nsc372920;4-hydroxy-3-propionyl-2H-chromen-2-one;2H-1-benzopyran-2-one, 4-hydroxy-3-(1-oxopropyl)-;4-Hydroxy-3-propionyl-chromen-2-one
• CAS NO: 4139-73-5
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.2054
• Mol File: 4139-73-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 123 °C
• Boiling Point: 353.9°Cat760mmHg
• Flash Point: 138.1°C
• Appearance: /
• Density: 1.382g/cm³
• Vapor Pressure: 1.28E-05mmHg at 25°C
• Refractive Index: 1.616
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-hydroxy-3-propionyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-3-propionyl-2H-chromen-2-one(4139-73-5)
• EPA Substance Registry System: 4-hydroxy-3-propionyl-2H-chromen-2-one(4139-73-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 4139-73-5(Hazardous Substances Data)

Usage

General Description

4-hydroxy-3-propionyl-2H-chromen-2-one is a chemical compound with the molecular formula C11H10O4. It is a derivative of coumarin, a natural compound found in several plants and used as a flavoring agent and in perfumes. This specific derivative has a hydroxyl group and a propionyl group attached to the coumarin core, giving it antioxidant and anti-inflammatory properties. It has been studied for its potential therapeutic effects, particularly in relation to its anti-cancer and anti-diabetic activities. 4-hydroxy-3-propionyl-2H-chromen-2-one is also being investigated for its potential as a drug delivery system and in the development of novel pharmaceutical agents.

InChI:InChI=1/C12H10O4/c1-2-8(13)10-11(14)7-5-3-4-6-9(7)16-12(10)15/h3-6,15H,2H2,1H3

Upstream product

• 20349-86-4 Methyl 3-(2-hydroxy-phenyl)-3-oxopropanoate 
• 123-62-6 propionic acid anhydride 
• 36953-85-2 4-propionyloxy-coumarin 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 802294-64-0 propionic acid 

Downstream Products

• 85689-29-8 (3-Ethyl-5-hydroxy-1-phenyl-1H-pyrazol-4-yl)-(2-hydroxy-phenyl)-methanone 
• 85689-36-7 3-Ethyl-1-phenyl-1H-chromeno[2,3-c]pyrazol-4-one 

Relevant articles and documents

Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins

Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-2H-chromen-2-one; BHC) was previously discovered to inhibit skeletal myosin II. BHC and 34 analogues were synthesized to explore structure-activity relationships. The properties of analogues, including solubility, stability, and toxicity, suggest that the BHC scaffold may be useful for developing therapeutics. Inhibition of actin-activated ATPase activity of fast skeletal and cardiac muscle myosin II, inhibition of skeletal muscle contractility ex vivo, and slowing of in vitro actin-sliding velocity were measured. Several analogues with aromatic side arms showed improved potency (half-maximal inhibitory concentration (IC50) 1 μM) and selectivity (≥12-fold) for skeletal myosin versus cardiac myosin compared to BHC. Several analogues blocked neurotransmission, suggesting that they are selective for nonmuscle myosin II over skeletal myosin. Competition and molecular docking studies suggest that BHC and blebbistatin bind to the same site on myosin.

CONJUGATE ADDITION OF CUPRATE REAGENTS TO CHROMONES: A ROUTE TO 2-SUBSTITUTED CHROMAN-4-ONES

Chromones (4-oxo-4H-1-benzopyrans) activated by electron-withdrawing groups attached to C-3 undergo efficient 1,4-addition of cuprate reagents, producing 2,3-disubstituted chroman-4-ones.The addition products from methyl chromone-3-carboxylates can be converted into 2-substituted chroman-4-ones by treatment with sodium chloride in wet dimethylsulphoxide.