64231-10-3

Basic information

• Product Name: 4-ETHOXY-7-HYDROXY-CHROMEN-2-ONE
• Synonyms: 4-Ethyl-7-hydroxychromen-2-one;4-Ethyl-7-hydroxycoumarin;4-Ethyl-7-hydroxy-2H-chromen-2-one;4-ethyl-7-hydroxy-2-chromenone
• CAS NO: 64231-10-3
• Molecular Formula: C₁₁H₁₀O₃
• Molecular Weight: 190.19
• Mol File: 64231-10-3.mol

Chemical Properties

• Boiling Point: 383.3 °C at 760 mmHg
• Flash Point: 173.5 °C
• Appearance: /
• Density: 1.258g/cm³
• Vapor Pressure: 2.01E-06mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 4-ETHOXY-7-HYDROXY-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ETHOXY-7-HYDROXY-CHROMEN-2-ONE(64231-10-3)
• EPA Substance Registry System: 4-ETHOXY-7-HYDROXY-CHROMEN-2-ONE(64231-10-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 64231-10-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Ethoxy-7-hydroxy-chromen-2-one is used as a pharmaceutical compound for its potential therapeutic applications in treating various diseases and conditions. Its antioxidant, anti-inflammatory, and anticancer properties make it a promising candidate for the development of new drugs.
Used in Medicinal Chemistry Research:
4-Ethoxy-7-hydroxy-chromen-2-one is used as a subject of interest in medicinal chemistry research due to its unique chemical structure and potential pharmacological activities. Researchers are exploring its properties and mechanisms of action to better understand its potential applications and optimize its therapeutic effects.

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

Upstream product

• 7664-93-9 sulfuric acid 
• 108-46-3 recorcinol 
• 4949-44-4 ethyl propanoylacetate 
• 33279-01-5 3-oxo-pentanenitrile 

Downstream Products

• 433307-98-3 C₁₈H₁₄O₄ 
• 218621-54-6 4-Ethyl-7-[(1R,2S,3S,4R)-2,3,4-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-chromen-2-one 
• 218621-55-7 4-Ethyl-7-[(1S,2R,3R,4S)-2,3,4-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohexyloxy]-chromen-2-one 
• 213037-83-3 4-Ethyl-7-((1R,2R,3S,4R)-2,3,4-trihydroxy-cyclohexyloxy)-chromen-2-one 
• 213037-82-2 4-Ethyl-7-[(1R,4R,5S,6S)-4,5,6-tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enyloxy]-chromen-2-one 

Relevant articles and documents

Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins

Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good

Dual functional small molecule fluorescent probes for image-guided estrogen receptor-specific targeting coupled potent antiproliferative potency for breast cancer therapy

A strategy by integrating biological imaging into early stages of the drug discovery process can improve our understanding of drug activity during preclinical and clinical study. In this article, we designed and synthesized coumarin-based nonsteroidal type fluorescence ligands for drug-target binding imaging. Among these synthesized compounds, 3e, 3f and 3h showed potent ER binding affinity and 3e (IC50?=?0.012?μM) exhibited excellent ERα antagonistic activity, its antiproliferative potency in breast cancer MCF-7 cells is equipotent to the approved drug tamoxifen. The fluorescence of compounds 3e and 3f depended on the solvent properties and showed significant changes when mixed with ERα or ERβ in vitro. Furthermore, target molecule 3e could cross the cell membrane, localize and image drug-target interaction in real time without cell washing. Thus, the coumarin-based platform represents a promising new ER-targeted delivery vehicle with potential imaging and therapeutic properties.

Method for the diagnosis of lysosomal storage diseases

The present invention relates to a method for the diagnosis of a lysosomal storage disease (LSD) in a subject which is based on determining the activity of lysosomal enzymes with the help of 4-alkyl umbelliferyl derivatives. The present invention further relates to said 4-alkyl umbelliferyl derivatives for use in the diagnosis of an LSD, and a kit for the diagnosis of an LSD.

Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes

The structure of osthole has been modified to improve its larvicidal activity against mosquitoes. A new efficient synthesis of osthole derivatives with Grignard reagents has been developed, which employs CuI and LiCl as promoters and covers a broad range of substrates to afford the corresponding products in mild to good yields (up to 83%). Bio-activity evaluation showed that several products exhibited better activities than osthole. CuI and LiCl promoted efficient synthesis of osthole derivatives with Grignard reagents has been developed. Bio-activity evaluation showed that several products exhibited far better larvicidal activities against mosquitoes than osthole.

BENZOPYRONE DERIVATIVE AND USE THEREOF

The present invention relates to the field of pharmaceutical chemistry, and in particular, to a benzopyrone derivative and a use thereof. The benzopyrone derivative is compound having a structure of formula (I) or a pharmaceutically acceptable salt thereof. It has been found by experiments that, this type of compounds is useful in prevention or treatment of neuropsychical diseases.

BENZOPYRONE DERIVATIVE AND USE THEREOF

The present invention relates to the field of pharmaceutical chemistry, and in particular, to a benzopyrone derivative and a use thereof. The benzopyrone derivative is compound having a structure of formula (I) or a pharmaceutically acceptable salt thereof. It has been found by experiments that, this type of compounds is useful in prevention or treatment of neuropsychical diseases.

Synthesis and biological investigation of coumarin piperazine (piperidine) derivatives as potential multireceptor atypical antipsychotics

The discovery and synthesis of potential and novel antipsychotic coumarin derivatives, associated with potent dopamine D2, D3, and serotonin 5-HT1A and 5-HT2A receptor properties, are the focus of the present article. The most-promising derivative was 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl)butoxy) -4-methyl-8-chloro-2H-chromen-2-one (17m). This derivative possesses unique pharmacological features, including high affinity for dopamine D2 and D3 and serotonin 5-HT1A and 5-HT2A receptors. Moreover, it possesses low affinity for 5-HT2C and H1 receptors (to reduce the risk of obesity associated with chronic treatment) and hERG channels (to reduce the incidence of torsade des pointes). In animal models, compound 17m inhibited apomorphine-induced climbing behavior, MK-801-induced hyperactivity, and the conditioned avoidance response without observable catalepsy at the highest dose tested. Further, fewer preclinical adverse events were noted with 17m compared with risperidone in assays that measured prolactin secretion and weight gain. Acceptable pharmacokinetic properties were also noted with 17m. Taken together, 17m may constitute a novel class of drugs for the treatment of schizophrenia.

Coumarins as novel 17β-hydroxysteroid dehydrogenase type 3 inhibitors for potential treatment of prostate cancer

The synthesis and SAR studies of 3- and 4-substituted 7-hydroxycoumarins as novel 17β-HSD3 inhibitors are discussed. The most potent compounds from this series exhibited low nanomolar inhibitory activity with acceptable selectivity versus other 17β-HSD isoenzymes and nuclear receptors.

Microwave initiated reactions: Pechmann coumarin synthesis, Biginelli reaction, and acylation

An energy-efficient protocol has been developed for solvent-free reactions that are mildly exothermic but not spontaneous. The exothermic reaction mixture-on several g-scale-is exposed for about 30 s to low power (about 200 W) microwaves and then the microwave oven is switched off. After this short burst of energy, the exothermic reaction gets initiated and proceeds on its own to completion. A number of coumarins were synthesized by the Pechmann reaction using this strategy.