842-01-3

Basic information

• Product Name: 7 8-DIHYDROXY-4-PHENYLCOUMARIN
• Synonyms: 7,8-dihydroxy-4-phenyl-2-chromenone;7,8-dihydroxy-4-phenyl-chromen-2-one;7,8-dihydroxy-4-phenylchromen-2-one;LDN 0063260;Coumarin 8;4-Phenyldaphnetin
• CAS NO: 842-01-3
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Product Categories: API intermediates;Building Blocks;Coumarins;Heterocyclic Building Blocks
• Mol File: 842-01-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 190-195 °C(lit.)
• Boiling Point: 495.1 °C at 760 mmHg
• Flash Point: 193.8 °C
• Appearance: /
• Density: 1.443 g/cm³
• Vapor Pressure: 1.99E-10mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: 7 8-DIHYDROXY-4-PHENYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 7 8-DIHYDROXY-4-PHENYLCOUMARIN(842-01-3)
• EPA Substance Registry System: 7 8-DIHYDROXY-4-PHENYLCOUMARIN(842-01-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 842-01-3(Hazardous Substances Data)

Usage

General Description

7 8-Dihydroxy-4-phenylcoumarin is a chemical compound that belongs to the coumarin family. It is a derivative of coumarin, a natural substance found in plants such as tonka beans and sweet woodruff, and is known for its anticoagulant and antioxidant properties. 7 8-DIHYDROXY-4-PHENYLCOUMARIN has been studied for its potential therapeutic applications in the treatment of various diseases, including cancer, diabetes, and cardiovascular disorders. Additionally, 7 8-dihydroxy-4-phenylcoumarin has been shown to exhibit significant anti-inflammatory and neuroprotective effects, making it a promising candidate for further research and drug development. Overall, this compound represents a potentially valuable resource for the development of novel pharmaceuticals with a range of therapeutic benefits.

InChI:InChI=1/C15H10O4/c16-12-7-6-10-11(9-4-2-1-3-5-9)8-13(17)19-15(10)14(12)18/h1-8,16,18H

Upstream product

• 87-66-1 2-hydroxyresorcinol 
• 525-52-0 pyrogallol triacetate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1610522-93-4 7,8-bis(benzyloxy)-4-hydroxy-2H-chromen-2-one 
• 1643318-41-5 ethyl 3-(3,4-bis(benzyloxy)phenyl)-3-oxopropanoate 
• 2652-27-9 1-(3,4-bis(benzyloxy)-2-hydroxyphenyl)ethanone 
• 1642785-09-8 7,8-bis(benzyloxy)-2-oxo-2H-chromen-4-yl trifluoromethanesulfonate 
• 24258-37-5 7,8-diacetoxy-4-phenylcoumarin 

Downstream Products

• 24258-37-5 7,8-diacetoxy-4-phenylcoumarin 
• 24258-36-4 8-hydroxy-7-methoxy-4-phenyl-2H-chromen-2-one 
• 1211944-11-4 7-hydroxy-8-methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1393371-51-1 7,8-bis(tert-butyldimethylsilyloxy)-4-phenyl-2H-chromen-2-one 
• 1181376-51-1 AD-C-002P-WZ₀₁₀₂₉ 
• 1181375-81-4 AD-C-001S-WZ₀₁₀₁₁ 
• 1181377-13-8 8-hydroxy-4-phenyl-7-(tetrahydro-2H-pyran-2-yloxy)-2H-chromen-2-one 
• 141925-12-4 20-Phenyl-2,5,8,11,14,17-hexaoxa-tricyclo[13.8.0.0^16,21]tricosa-1⁽¹⁵⁾,16⁽²¹⁾,19,22-tetraen-18-one 
• 2555-35-3 7,8-Dimethoxy-4-phenyl-2H-1-benzopyran-2-one 

Relevant articles and documents

Synthesis and structure-activity relationship of daphnetin derivatives as potent antioxidant agents

In this study, daphnetin 1 was chosen as the lead compound, and C-3 or C-4-substituted daphnetins were designed and synthesized to explore the potential relationship between the antioxidant activities and the chemical structures of daphnetin derivatives. The antioxidant activities of the generated compounds were evaluated utilizing the free radical scavenging effect on 2,2-diphenyl-1-picrylhydrazyl, 2,2-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation, and the ferric reducing power assays, and were then compared with those of the standard antioxidant Trolox. The results showed that the catechol group was the key pharmacophore for the antioxidant activity of the daphnetins. The introduction of an electron-withdrawing hydrophilic group at the C-4 position of daphnetin enhanced the antioxidative capacity, but this trend was not observed for C-3 substitution. In addition, introduction of a a hydrophobic phenyl group exerted negative effects on the antioxidant activity in both the C-3 and C-4 substitutions. Among all of the derivatives tested, the most powerful antioxidant was 4-carboxymethyl daphnetin (compound 9), for which the strongest antioxidant activity was observed in all of the assays. In addition, compound 9 also displayed strong pharmaceutical properties in the form of metabolic stability. To summarize, compound 9 holds great potential to be developed as an antioxidant agent with excellent antioxidant activity and proper pharmacokinetic behavior.

Meglumine sulfate catalyzed solvent-free one-pot synthesis of coumarins under microwave and thermal conditions

A convenient method has been developed for the Pechmann reaction of phenols and β-keto esters catalyzed by meglumine sulfate. Solvent-free conditions, inexpensive catalyst, short reaction times, high yield, and ease of purification of the products are the advantages of this protocol. This novel catalytic system is expected to contribute to the development of more benign Pechmann condensation reactions of phenols with β-keto esters.

Environmentally sustainable magnetic solid sulfonic acid: An efficient and reusable catalyst for the Pechmann reaction

Abstract An environmentally benign sulfonic acid nanocomposite based on Fe3O4@SiO2 core-shell magnetic nanoparticles, Fe3O4@SiO2@Et-PhSO3H, was prepared and the acidity and utility of the catalyst were explored for the synthesis of a diverse range of coumarin derivatives under solvent-free conditions. The catalyst shows potential for scale up in the synthesis of coumarins with high purity and was easily separated by using an external magnet. The recovered catalyst was reused in seven cycles without any significant loss of activity.