21392-48-3

Basic information

• Product Name: 7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE
• Synonyms: 7-hydroxy-8-methyl-4-phenyl-2-chromenone;7-hydroxy-8-methyl-4-phenyl-chromen-2-one;7-hydroxy-8-methyl-4-phenylchromen-2-one;7-hydroxy-8-methyl-4-phenyl-coumarin
• CAS NO: 21392-48-3
• Molecular Formula: C₁₆H₁₂O₃
• Molecular Weight: 252.27
• Mol File: 21392-48-3.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 457.9°Cat760mmHg
• Flash Point: 199.7°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 5.25E-09mmHg at 25°C
• Refractive Index: 1.651
• CAS DataBase Reference: 7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE(21392-48-3)
• EPA Substance Registry System: 7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE(21392-48-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 21392-48-3(Hazardous Substances Data)

Usage

General Description

7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE, also known as HMC, is a chemical compound belonging to the family of chromones. 7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE can be synthesized and has been found to exhibit various pharmacological properties, including antioxidant, anti-inflammatory, and anti-cancer activities. Its antioxidant properties make it a potential candidate for the development of new drugs for the treatment of oxidative stress-related diseases, while its anti-inflammatory and anti-cancer activities could be utilized in the development of novel therapeutics for inflammatory and cancer-related conditions. Additionally, HMC has shown potential as a neuroprotective agent, making it an interesting compound for further research and development in the field of neurology. Overall, 7-HYDROXY-8-METHYL-4-PHENYL-2H-CHROMEN-2-ONE has demonstrated promising pharmacological properties, making it a valuable compound for further study and potential therapeutic applications.

InChI:InChI=1/C16H12O3/c1-10-14(17)8-7-12-13(9-15(18)19-16(10)12)11-5-3-2-4-6-11/h2-9,17H,1H3

Upstream product

• 608-25-3 2-methylbenzene-1,3-diol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 87-66-1 2-hydroxyresorcinol 
• 65-85-0 benzoic acid 
• 93-89-0 benzoic acid ethyl ester 
• 2216-94-6 phenylpropynoic acid ethyl ester 

Downstream Products

• 314742-99-9 8-methyl-7-(1-methyl-2-oxo-2-phenylethoxy)-4-phenylcoumarin 
• 25944-34-7 7-acetoxy-8-methyl-4-phenylchromen-2-one 
• 25944-21-2 9-methyl-3,5-diphenyl-7H-furo[3,2-g]chromen-7-one 

Relevant articles and documents

Synthesis of Novel Anti-inflammatory Psoralen Derivatives?-?Structures?with?Distinct?Anti-Inflammatory?Activities

As a continuum to our work with coumarins, 12 psoralens were synthesized and evaluated for their anti-inflammatory activity. Psoralens were prepared in three steps; at first, 7-hydroxycoumarins were synthesized by von Pechmann condensation and then converted to 7-(2-oxopropoxy)coumarins. In the final step, a fused furan ring was introduced in an intramolecular ring-formation reaction. Based on a SciFinder search, two out of the 12 synthesized psoralen derivatives (compounds 9 and 12) were found to be novel. The derivatives displayed anti-inflammatory activity by suppressing iNOS and IL-6 expression, but their mechanism of action seemed to be dependent on the substitution. Compound 6 with propyl side chain inhibited NF-κB mediated transcription, while compound 10 with a phenyl substituent down-regulated iNOS expression in a posttranscriptional manner. The results introduce psoralen derivatives as promising anti-inflammatory compounds with potential for treatment of conditions involving iNOS and/or IL-6-mediated adverse responses.

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.

7-substituted-4-aryl coumarins compound, and preparation method and application thereof

The invention discloses a 7-substituted-4-aryl coumarins compound, and a preparation method and an application thereof and belongs to the technical field of antitumor drugs. The 7-substituted-4-aryl coumarins compound is acquired in the manner of modifying and remolding 4 and 7 loci of the coumarins. The structural formula is shown in the specification. A pharmacological experiment proves that such a compound has an excellent antitumor activity, can be used for preparing the antitumor drugs, is capable of supplying a new selection for the development and application of the antitumor drugs and further can be applied to the design and optimization of the antitumor drugs. The preparation method of the compound has the advantages of easily acquired raw materials, mild reaction condition, easily realized synthesis method, simple reaction process and operation, low-cost reagents and higher yield.