4-Hydroxy Coumarin

Product Description

4Hydroxycoumarin is a naturally occurring compound and a significant building block in organic chemistry particularly for the synthesis of anticoagulant drugs like warfarin Heres an indepth look

 Chemical Information

 Chemical Name 4Hydroxycoumarin  

 Chemical Formula C9H6O3  

 Molecular Weight 16214 gmol  

 Structure  

   A coumarin derivative with a hydroxyl group OH at the 4th position of the fused benzopyrone ring system  

 Physical Properties

 Appearance White to offwhite crystalline powder  

 Melting Point 220224C  

 Solubility  

   Slightly soluble in water  

   Soluble in organic solvents like ethanol methanol and acetone

 Natural Occurrence

4Hydroxycoumarin is a metabolite derived from coumarin a compound found in many plants particularly in the Tonka bean and sweet clover

 Applications

1 Pharmaceutical Industry  

    Anticoagulants  

      Used as a precursor for synthesizing bloodthinning agents like warfarin acenocoumarol and dicoumarol  

      These compounds inhibit vitamin K epoxide reductase reducing blood clotting  

    Potential Antimicrobial Agents Investigated for antibacterial and antifungal properties  

2 Chemical Synthesis  

    A versatile intermediate for creating more complex coumarin derivatives in drug development and materials chemistry  

3 Biological Research  

    Used in studies related to enzymatic inhibition and its role in metabolic pathways involving coumarins

 Reactivity

 Phenolic Hydroxyl Group OH  

   Can undergo esterification or etherification reactions  

   Acts as a nucleophile in various organic reactions  

 Lactone Ring  

   Stable under neutral and slightly acidic conditions  

   Susceptible to hydrolysis under strong alkaline conditions to yield coumarinic acid

 Electrophilic Substitution  

   The aromatic system of the coumarin ring can participate in reactions like nitration halogenation or sulfonation

 Safety and Handling

 Toxicity  

   Generally low toxicity but derivatives such as warfarin require careful handling due to anticoagulant effects  

 Handling  

   Use gloves goggles and a lab coat when handling  

   Work in a wellventilated area to avoid inhaling dust  

 Storage  

   Store in a cool dry and dark place away from oxidizing agents

 Synthesis

 Typically synthesized by the Pechmann condensation of phenol and keto esters under acidic conditions  

 Alternatively it can be derived by hydroxylation of coumarin

Would you like to explore its synthesis in detail its role in anticoagulant therapy or its use in specific industrial applications