55005-28-2

Basic information

• Product Name: 6-ETHYL-4-HYDROXYCOUMARIN
• Synonyms: 6-ETHYL-4-HYDROXYCOUMARIN;6-ETHYL-4-HYDROXY-2H-CHROMEN-2-ONE;6-Ethyl-4-hydroxycoumarine;6-ethyl-4-hydroxychromen-2-one
• CAS NO: 55005-28-2
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.2
• Mol File: 55005-28-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 216-218°C
• Boiling Point: 374.521°C at 760 mmHg
• Flash Point: 168.875°C
• Appearance: /
• Density: 1.313g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.62
• CAS DataBase Reference: 6-ETHYL-4-HYDROXYCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 6-ETHYL-4-HYDROXYCOUMARIN(55005-28-2)
• EPA Substance Registry System: 6-ETHYL-4-HYDROXYCOUMARIN(55005-28-2)

Safety Data

• Hazardous Substances Data: 55005-28-2(Hazardous Substances Data)

Usage

Chemical compound

6-Ethyl-4-hydroxycoumarin

Category

Coumarin derivatives

Derivative of

Coumarin

Properties

Anticoagulant and anti-inflammatory

Uses

Widely used in pharmaceutical industry

Potential therapeutic effects

Studied for treatment of cancer and cardiovascular disorders

Chemical structure

Hydroxyl group at 4-position, ethyl group at 6-position

InChI:InChI=1/C11H10O3/c1-2-7-3-4-10-8(5-7)9(12)6-11(13)14-10/h3-6,12H,2H2,1H3

Upstream product

• 123-07-9 4-Ethylphenol 
• 141-82-2 malonic acid 
• 24539-92-2 3-ethyl-6-hydroxyacetophenone 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 1309854-97-4 7-ethyl-1,2,3,3-tetraphenylcyclopenta[b]chromen-9(3H)-one 
• 1449795-44-1 C₂₅H₁₉NO₂ 

Relevant articles and documents

Synthesis, characterization, and anticoagulant activity of new functionalized biscoumarins

Despite their rarity and structural complexity, natural and synthetic biscoumarins have polarized much attention from investigators particularly due to their characteristic activity as anticoagulant agents. In this work, a panel of twelve functionalized biscoumarins was synthesized in two schematic steps; the first one started by condensing various phenol-based derivatives with malonic acid via a Pechmann-type reaction yielding alkyl-substituted 4-hydroxycoumarins herein symbolized as (E1-E12). The latter compounds were undergone a self-coupling under the influence of methylene iodide to afford the target functionalized biscoumarins, which were symbolized as (EY1-EY12). The potential of the synthesized biscoumarins as anticoagulant applicants was investigated in vivo using rabbit as an animal model. The employed assay was the prothrombin time that was monitored after three and five days of the last oral treatment. The results gathered from this test revealed that the synthesized biscoumarins have a promising anticoagulant activity compared with warfarin as a standard anticoagulant drug, with privileged influence contributed to those substituted at position 7 of the coumarin framework. The authors concluded that the substitution of an alkyl group at that position of the coumarin monomer may intensify the anticoagulant activity of the prepared biscoumarins. Also, this intensity was directly proportionated to the increase in the molecular weight of this alkyl group. Accordingly, the synthesized biscoumarins possessing this property would provide an efficient base for synthesizing new compounds, which have a promising anticoagulant effect.

Coumarin derivatives for the treatment of allergies

Pharmaceutical compositions for the treatment of allergies are produced using coumarin derivatives as the active agent. Certain of these compounds and their salts are novel.