39513-75-2

Basic information

• Product Name: 6-METHYL-4-CHROMANONE
• Synonyms: 6-METHYL-4-CHROMANONE;6-METHYLCHROMAN-4-ONE;6-METHYLCHROMANONE;6-METHYL-4-CHROMANONE 95.0%;6-METHYL-4-CHROMONE;6-Methylchromanone (6-Methylchroman-4-one);2,3-Dihydro-6-methyl-4H-1-benzopyran-4-one;6-Methyl-2,3-dihydro-4H-1-benzopyran-4-one
• CAS NO: 39513-75-2
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Product Categories: Benzopyrans;Building Blocks;Heterocyclic Building Blocks
• Mol File: 39513-75-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 31-35 °C(lit.)
• Boiling Point: 141-143 °C13.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.071 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000949mmHg at 25°C
• Refractive Index: 1.5550
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 6-METHYL-4-CHROMANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYL-4-CHROMANONE(39513-75-2)
• EPA Substance Registry System: 6-METHYL-4-CHROMANONE(39513-75-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 39513-75-2(Hazardous Substances Data)

Usage

Description

6-METHYL-4-CHROMANONE is an organic compound with the molecular structure featuring a chromanone core and a methyl group at the 6th position. It is known for its potential applications in various fields due to its unique chemical properties.

Uses

Used in Enzyme Research:
6-METHYL-4-CHROMANONE is used as a substrate for carbonyl reductase from Sporobolomyces salmonicolor, where it is reduced to the corresponding (R)-chiral alcohol. This application is significant for studying enzyme mechanisms and their role in biotransformation processes.
Used in Biocatalyst Research:
6-METHYL-4-CHROMANONE is also used as a substrate for the enantioselective reduction by three biocatalysts, namely, Didymosphaeria igniaria, Coryneum betulinum, and Chaetomium sp. This application is crucial for understanding the selectivity and efficiency of these biocatalysts in producing enantiomerically pure compounds, which are essential in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
6-METHYL-4-CHROMANONE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for developing new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
6-METHYL-4-CHROMANONE is used as a key intermediate in the synthesis of various organic compounds, including natural products and specialty chemicals. Its versatility in chemical reactions allows for the development of novel compounds with diverse applications.
Used in Analytical Chemistry:
6-METHYL-4-CHROMANONE can be employed as a reference compound or a standard in analytical chemistry for the development and validation of analytical methods, such as high-performance liquid chromatography (HPLC) and gas chromatography (GC), to ensure accurate and reliable results.

InChI:InChI=1/C10H10O2/c1-7-2-3-10-8(6-7)9(11)4-5-12-10/h2-3,6H,4-5H2,1H3

Upstream product

• 13102-87-9 3-chloro-1-(2-hydroxy-5-methylphenyl)propan-1-one 
• 25173-37-9 3-(4-methylphenoxy)propionic acid 
• 36763-48-1 4-p-tolyloxy-but-2-yn-1-ol 
• 117543-35-8 4-chloro-6-methyl-2H-chromene 
• 117543-23-4 1-(3-Chloro-prop-2-ynyloxy)-4-methyl-benzene 
• 115997-62-1 1-(3-Bromo-prop-2-ynyloxy)-4-methyl-benzene 
• 38445-23-7 6-methyl-chromen-4-one 
• 1121-70-6 sodium 4-methylphenoxide 
• 106-44-5 p-cresol 
• 107-13-1 acrylonitrile 
• 106942-84-1 1-(3-bromo-2-methoxy-5-methylphenyl)-1-ethanone 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 56609-15-5 3'-bromo-2'-hydroxy-5'-methylacetophenone 
• 1225533-42-5 C₁₂H₁₆O₃ 

Downstream Products

• 1031206-36-6 IMS 2186 
• 638220-39-0 6-methylchroman-4-amine 
• 1220452-71-0 3-(4-hydroxyphenyl)-6-methylchroman-4-one 
• 140870-50-4 6-methyl-3-phenylchroman-4-one 
• 720684-44-6 (4-chloro-phenyl)-(4-isocyanato-6-methyl-chroman-4-yl)-diazene 
• 720684-39-9 (4-isocyanato-6-methyl-chroman-4-yl)-phenyl-diazene 

Relevant articles and documents

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Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.