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

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

Uses

Used in Pharmaceutical Industry:
7,8-Dihydroxy-4-phenylcoumarin is used as a therapeutic agent for the treatment of various diseases, such as cancer, diabetes, and cardiovascular disorders, due to its potential therapeutic applications and beneficial properties.
Used in Anticancer Applications:
In the field of oncology, 7,8-dihydroxy-4-phenylcoumarin is utilized as an anticancer agent, targeting the treatment of various types of cancer. Its potential therapeutic benefits in this area are attributed to its anticoagulant and antioxidant properties.
Used in Anti-inflammatory Applications:
7,8-Dihydroxy-4-phenylcoumarin is employed as an anti-inflammatory agent, leveraging its significant anti-inflammatory effects to alleviate inflammation and associated symptoms in various conditions.
Used in Neuroprotective Applications:
In the realm of neurology, 7,8-dihydroxy-4-phenylcoumarin is used as a neuroprotective agent, capitalizing on its neuroprotective effects to safeguard neurons and mitigate neurodegenerative processes in conditions such as Alzheimer's disease and Parkinson's disease.
Overall, 7,8-dihydroxy-4-phenylcoumarin's diverse range of applications across different industries highlights its potential as a versatile and valuable compound in the development of novel pharmaceuticals for a variety of therapeutic purposes.

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

• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 87-66-1 2-hydroxyresorcinol 
• 525-52-0 pyrogallol triacetate 
• 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

• 24258-36-4 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 
• 24258-37-5 7,8-diacetoxy-4-phenylcoumarin 
• 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.

SnCl4 grafted on silica gel: an efficient catalyst for solvent-free synthesis of coumarins via the Pechmann condensation

A facile synthesis of substituted coumarins via Pechmann condensation catalyzed by SnCl4 grafted on silica gel is described, which was conducted under solvent-free condition in high yields. The catalyst is noncorrosive and can be easily prepared and separated from the reaction mixture. This methodology offers some advantages with regard to yield of products, simplicity in operation and green aspects.

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.

Preparation and pharmacological effects of coumarin derivative and application of coumarin derivative to treatment on pruritus

The invention relates to preparation of a coumarin derivative 7,8-dihydroxy-4-trifluoromethyl-chromene-2H-chromen-2-one for treating the pruritus symptom, studies of pharmacodynamics on the aspects of a molecular pharmacology mechanism, a pruritus animal model and the like of the coumarin derivative, and a pharmaceutics study applicable to treatment on pruritus. The active compound is definite in pharmacological effect mechanism, is broad-spectrum and effective to treat the pruritus symptom, and can be used for clinical application to treatment on skin diseases.

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.

Synthesis and anticancer activity of 7,8-dihydroxy-4-arylcoumarins

A series of 7,8-dihydroxy-4-arylcoumarins, the derivatives related to DW532 that was an anti-tumor agent targeting both kinase and tubulin, was prepared by Suzuki coupling reaction. Among them, compounds 6a, 6b, and 6c were found to exhibit anti-prolifera

Silica supported boric tri-sulfuric anhydride as a novel and efficient catalyst for solvent-free synthesis of coumarins via Pechmann condensation

It is found that silica supported boric trisulfuric anhydride (BTSA.SiO2) is a novel, suitable and versatile catalyst for efficient and clean synthesis of coumarins via Pechmann cyclocondensation under mild and solvent-free conditions. Different kinds of

Cux2 (x =cl, br) as catalysts for pechmann reaction: Synthesis of 4-substituted coumarins

CuX2 (X=Cl, Br) are found to be efficient catalysts (10 mol%) for the Pechmann condensation reaction of phenols and b-ketoesters to give 4-substituted coumarins under solvent-free conditions. The yields of coumarin derivatives obtained via this

Ceric ammonium nitrate (CAN): An efficient catalyst for the coumarin synthesis via Pechmann condensation using conventional heating and microwave irradiation

An efficient and convenient method for the synthesis of substituted coumarins via Pechmann condensation of different phenols with ethylacetoacetate in the presence of ammonium cerium(IV) nitrate as the catalyst in a solvent- free media using both conventional heating and microwave irradiation. Copyright Taylor & Francis Group, LLC.

Microwave-promoted automated synthesis of a coumarin library

A 30-membered library of coumarins has been synthesized in a microwave-assisted Pechmann reaction using neat trifluoroacetic acid both as an acidic reagent and a reaction medium. Alternatively, polymer-supported sulfonic acid Amberlyst-15 could also be employed to facilitate the formation of coumarins. The use of a specially-built microwave synthesizer with liquid handling tools rendered the automated synthesis of a coumarin library feasible.