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3,3'-Ethylidenebis[4-hydroxy-2-benzopyrone], also known as Daphnetin, is a coumarin derivative with a molecular formula of C16H10O6. It is a yellow crystalline compound found in several plant species, such as Daphne odora. Daphnetin exhibits potential antioxidant, anti-inflammatory, anticoagulant, antiviral, and antimicrobial properties, making it a promising candidate for pharmaceutical applications in the treatment of various diseases.

1821-16-5

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1821-16-5 Usage

Uses

Used in Pharmaceutical Industry:
3,3'-Ethylidenebis[4-hydroxy-2-benzopyrone] is used as a therapeutic agent for its potential antioxidant, anti-inflammatory, and anticoagulant properties. It is being studied for its potential use in the treatment of various diseases, such as cancer, cardiovascular diseases, and inflammatory disorders.
Used in Antiviral and Antimicrobial Applications:
3,3'-Ethylidenebis[4-hydroxy-2-benzopyrone] is used as an antiviral and antimicrobial agent due to its demonstrated antiviral and antimicrobial activities. This makes it a compound of interest for potential pharmaceutical applications in combating viral and microbial infections.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of 3,3'-ethylidenebis[4-hydroxy-2-benzopyrone], novel drug delivery systems are being developed. These systems aim to improve the compound's delivery, solubility, and efficacy in treating various diseases by employing carriers such as organic and metallic nanoparticles.

Check Digit Verification of cas no

The CAS Registry Mumber 1821-16-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,2 and 1 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1821-16:
(6*1)+(5*8)+(4*2)+(3*1)+(2*1)+(1*6)=65
65 % 10 = 5
So 1821-16-5 is a valid CAS Registry Number.

1821-16-5Downstream Products

1821-16-5Relevant academic research and scientific papers

Ca(II)-catalyzed, one-pot four component synthesis of functionally embellished benzylpyrazolyl coumarins in water

Yaragorla, Srinivasarao,Pareek, Abhishek,Dada, Ravikrishna

supporting information, p. 4770 - 4774 (2015/07/20)

A facile one-pot, four-component synthesis of biologically important benzylpyrazolyl coumarins in water has been demonstrated using environmentally benign Ca(II) as the catalyst. Participation of aliphatic aldehydes has been described for the first time. Short reaction times, high yields and chromatography free isolation of the products, usage of eco-friendly catalyst and solvent are the key features of this method.

Biscoumarin: New class of urease inhibitors; Economical synthesis and activity

Khan, Khalid Mohammed,Iqbal, Sajid,Lodhi, Muhammad Arif,Maharvi, Ghulam Murtaza,Zia-Ullah,Choudhary, Muhammad Iqbal,Atta-ur-Rahman,Perveen, Shahnaz

, p. 1963 - 1968 (2007/10/03)

A variety of biscoumarins (1-21) with variable substituents at C-11 were synthesized with an improved method and evaluated as urease inhibitors. The synthesized compounds showed varying degree of urease inhibitory activity ranging from 15.06-91.35 μM. The size and electron donating or withdrawing effects of substituents influenced the activity, which lead to the urease inhibitors.

The Chemistry of Coumarin Derivatives Synthesis of 3-Alkyl-4-hydroxycoumarins by Reductive Fragmentation of 3,3'-Alkylidene-4,4'-dihydroxybis

Appendino, Giovanni,Cravotto, Giancarlo,Tagliapietra, Silvia,Ferraro, Stefano,Nano, Gian Mario,Palmisano, Giovanni

, p. 1451 - 1458 (2007/10/02)

Treatment of 3,3'-alkylidene-4,4'-dihydroxybis 1 with NaBH3CN in refluxing MeOH affords 3-alkyl-4-hydroxycoumarins 2 and 4-hydroxycoumarin (3; Scheme 1).The reaction may take place via hydride trapping of alkylidenechromandiones C formed from 1 in a retro-Michael reaction.Such a retro-Michael reaction of 1 might be biologically relevant.The presence of C during the reductive fragmentation 1 --> 2 is suggested by Diels-Alder and nucleophilic trapping of the alkylidenechromandiones C as well as from cross-over experiments with coumarins other than 3 (see Scheme 2).The reductive fragmentation of 1 allows the chemo- and regioselective synthesis of a variety of 3-alkyl-4-hydroxycoumarins 2 (see Table).

Quantitative structure activity relationships for dicoumarol antivitamins K in the uncoupling of mitochondrial oxidative phosphorylation

Labbe Bois,Laruelle,Godfroid

, p. 85 - 90 (2007/10/05)

The dynamic structure of dicoumarol derivatives substituted on the methylene bridge was studied by nuclear magnetic resonance (nmr) spectroscopy. These molecules may be considered as dimers with restricted rotation around the methylene bridge, held by intramolecular hydrogen bonds; the presence of the substituent R modifies this dynamic process, mainly the facility of exchange of the 2 hydroxyl protons. These compounds were compared in respect of their potency in uncoupling oxidative phosphorylation in pig heart mitochondria; the data were correlated with constants used to characterize the substituent R; to make a potent uncoupler, R should be as small and as hydrophilic as possible. The results are discussed in consonance with the postulated mechanisms of action of the uncouplers, but no simple conclusion could be drawn, especially concerning the role of the dissociable protons.

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