6093-68-1

Usage

Uses

Used in Pharmaceutical Industry:
6-Hydroxycoumarin is used as a pharmaceutical compound for its anti-inflammatory, anti-pyretic, and anti-oxidant properties. It can be employed in the development of drugs to treat various inflammatory and infectious diseases, as well as conditions associated with oxidative stress.
Used in Organic Synthesis:
6-Hydroxycoumarin (CAS# 6093-68-1) is a valuable compound in organic synthesis, serving as a key intermediate in the production of various chemical compounds and pharmaceuticals. Its unique structure allows for further functionalization and modification, making it a useful building block in the synthesis of complex organic molecules.
Used in Antimicrobial Applications:
Due to its anti-bacterial, anti-fungal, and bacteriostatic properties, 6-Hydroxycoumarin can be used in the development of antimicrobial agents to combat various microbial infections. It can be incorporated into formulations for topical applications, such as creams and ointments, or developed into systemic drugs for treating internal infections.
Used in Anticancer Research:
6-Hydroxycoumarin's antitumor activity makes it a promising candidate for cancer research and drug development. It can be studied for its potential to target specific cancer cells, modulate signaling pathways, and enhance the efficacy of existing cancer therapies.
Used in Vasodilator Applications:
As a vasodilator, 6-Hydroxycoumarin can be used in the development of drugs to treat cardiovascular diseases, such as hypertension and angina. Its ability to relax blood vessels and improve blood flow can contribute to the management and treatment of these conditions.

Preparation

(1) synthesis of 6-aminocoumarins：In polar solvent, using 6- nitroscumarin as raw material, using hydrazine hydrate as hydrogen Source, is reducing catalyst using ferric chloride (FeCl36H2O), at ambient pressure reduces 6-nitroscumarin, prepare 6- aminocoumarins；(2) synthesis of 6-Hydroxycoumarins：In sulfuric acid solution, one-step method is by 6-aminocoumarins after diazo-reaction Direct hydrolysis, prepares 6-Hydroxycoumarins in high yield.The preparation method of 6 Hydroxycoumarins

Upstream product

• 3524-69-4 2-formyl-1,4-phenylene diacetate 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 91-64-5 coumarin 

Downstream Products

• 38489-73-5 2,5-dimethoxy-cis-cinnamic acid 
• 17372-53-1 6-methoxycoumarin 
• 213664-95-0 6-cyclohex-2-enyloxycoumarin 
• 10172-75-5 3,3-(4'-methoxybenzylidene)bis(4-hydroxycoumarin) 

Relevant academic research and scientific papers

Revisiting terephthalic acid and coumarin as probes for photoluminescent determination of hydroxyl radical formation rate in heterogeneous photocatalysis

We investigated in detail the applicability of two radical scavengers – coumarin (COUM) and terephthalic acid (TA) – as probe compounds in a widely used photoluminescent (PL) determination of OH? radical rate formation of photocatalysts. The study reveals that precautions must be taken when using either of the two compounds as neither allows a direct determination of the absolute OH? radical formation rate. Chromatographic analyses of irradiated COUM and TA solutions revealed that both probe compounds reacted via more than one pathway, out of which, only one pathway in each case yielded the measured photoluminescent 7-hydroxycoumarin (7-OHC) and 2-hydroxyterephthalic acid (TAOH), respectively. Applicability of both probes was also tested on three model TiO2-based catalysts (anatase TiO2 nanorods (TNR), anatase TiO2 nanoparticles (TNP), amorphous TiO2 nanorods (a-TNR)). Regardless of the probe compound used, the order of relative OH? radical formation rates determined for these catalysts was the same (TNR a-TNR) and in good correlation with the order of bisphenol A (BPA) degradation rates. This demonstrates that (i) formation of OH? radicals is the predominating criterion when probing a photocatalyst's activity (but not the only one) and that (ii) TA and COUM potentially enable a relative evaluation of photocatalytic materials, despite the numerous shortcomings of these probes. However, in order to allow for general inter-laboratory comparisons the photoluminescence method should clearly be standardized with precisely defined experimental parameters.

CYP2A13-catalysed coumarin metabolism: Comparison with CYP2A5 and CYP2A6

1. We investigated the total metabolism of coumarin by baculovirus (BV)-expressed CYP2A13 and compared it with metabolism by BV-expressed CYP2A6. The major coumarin metabolite formed by CYP2A13 was 7-hydroxycoumarin, which accounted for 43% of the total metabolism. The product of 3,4-epoxidation, o-hydroxyphenylacetaldehyde (o-HPA), accounted for 30% of the total metabolites. 2. The Km and Vmax for CYP2A13-mediated coumarin 7-hydroxylation were 0.48 ± 0.07 μM and 0.15 ± 0.006 nmol min-1 nmol-1 CYP, respectively. The Vmax of coumarin 7-hydroxylation by CYP2A13 was about 16-fold lower than that of CYP2A6, whereas the Km was 10-fold lower. 3. In the mouse, there were two orthologues for CYP2A6: CYP2A4 and CYP2A5, which differed by only 11 amino acids. However, CYP2A5 is an efficient coumarin 7-hydroxylase, where as CYP2A4 is not. We report here that BV-expressed CYP2A4 metabolizes coumarin by 3,4-epoxidation. Two products of the 3,4-epoxidation pathway, o-HPA and o-hydroxyphenylacetic acid (o-HPAA), were detected by radioflow HPLC. 4. The Km and Vmax for the coumarin 3,4-epoxidation by CYP2A4 were 8.7 ± 3.6 μM and 0.20 ± 0.04nmol min-1 nmol-1 CYP, respectively. Coumarin 7-hydroxylation by CYP2A5 was more than 200 times more efficient than 3,4 epoxidation by CYP2A4.

Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent. IV: Improved synthetic method of substituted coumarins

The reaction of salicylaldehydes (2) with Horner-Wadsworth-Emmons (HWE) or Ando-HWE reagents was attempted to afford intramolecular phosphonate derivatives (6). A new synthetic method for coumarins (1) was achieved by using protected 2.