68454-18-2

Basic information

• Product Name: 4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one
• Synonyms: 2H-1-benzopyran-2-one, 4-methyl-7-(2-oxopropoxy)-
• CAS NO: 68454-18-2
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.232
• Mol File: 68454-18-2.mol

Chemical Properties

• Boiling Point: 407.2°C at 760 mmHg
• Flash Point: 183.6°C
• Density: 1.227g/cm³
• Vapor Pressure: 7.67E-07mmHg at 25°C
• Refractive Index: 1.551
• CAS DataBase Reference: 4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one(68454-18-2)
• EPA Substance Registry System: 4-methyl-7-(2-oxopropoxy)-2H-chromen-2-one(68454-18-2)

Safety Data

• Hazardous Substances Data: 68454-18-2(Hazardous Substances Data)

Upstream product

• 108-46-3 recorcinol 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 584-08-7 potassium carbonate 
• 78-95-5 chloroacetone 
• 5980-33-6 sodium 4-methylumbelliferonate 

Downstream Products

• 1578238-12-6 N-(4-hydroxyphenyl)-3,5-dimethylbenzo[1,2-b:5,4-b']difuran-2-carboxamide 
• 1578238-10-4 N-(4-methoxyphenyl)-3,5-dimethylbenzo[1,2-b:5,4-b']difuran-2-carboxamide 
• 1578238-08-0 4-(3,5-dimethylbenzo[1,2-b:5,4-b']difuran-2-carboxamido)benzoic acid 
• 1578238-06-8 3,5-dimethyl-N-(p-tolyl)benzo[1,2-b:5,4-b']difuran-2-carboxamide 
• 1578238-15-9 3,5-dimethyl-N-phenylbenzo[1,2-b:5,4-b']difuran-2-carboxamide 
• 1578238-14-8 N-(4-chlorophenyl)-3,5-dimethylbenzo[1,2-b:5,4-b']difuran-2-carboxamide 
• 15183-96-7 3,5-dimethyl-7H-furo[3,2-g]chromen-7-one 

Relevant articles and documents

Improved synthesis, X-ray structure, and antifungal activity of a sugar-psoralen conjugate: 4,4′-Dimethylxanthotoxol 2,3,4,6-tetra-O-Acetyl-β-D-glucoside

An improved synthesis for 4,4′-dimethylxanthotoxol 2,3,4,6-tetra-O-acetyl-β-D-glucoside (1) starting from resorcinol was developed. Crystallographic analysis of glucoside 1 indicated that the dihedral angles between the mean planes of the tricyclic ring system of adjacent molecules was 54.820(22)° probably due to the steric hindrance caused by the bulky O-glucoside moiety, which prevents the molecules from packing via π···π stacking between the tricyclic cores. The antifungal screening data revealed that glucoside 1 had higher inhibition than its parent compound 4,4′-dimethylxanthotoxol and azoxystrobin against Rhizoctonia solani, Pyricularia grisea, and Alternaria alternate Japanese pear pathotype, with the inhibitory rates of 75.4, 65.7 and 70.1%, respectively, at the 50 μg/mL concentration.

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.

7-(2-Oxoalkoxy)coumarins: Synthesis and Anti-Inflammatory Activity of a Series of Substituted Coumarins

A series of 7-(2-oxoalkoxy)coumarins have been synthesized by conjugating substituted 7-hydroxycoumarins with different chloroketones. The anti-inflammatory properties of 7-(2-oxoalkoxy)coumarins were studied in LPS-induced inflammatory response in J774 macrophages. Western blot was used to determine the expression of iNOS and COX-2, NO was determined by measuring its metabolite nitrite by Griess reaction and IL-6 was measured by ELISA. Seventeen of the studied compounds inhibited NO and IL-6 production over 50% at 100 μM concentrations. IC50 values of the best inhibitors were 21 μM/24 μM (NO/IL-6) for compound 12 and 30 μM/10 μM (NO/IL-6) for compound 20. The main result was that the substitution with 7-(2-oxoalkoxy) group improved the anti-inflammatory properties of most of the investigated 7-hydroxycoumarins.

Synthesis and antimicrobial evaluation of amide derivatives of benzodifuran-2-carboxylic acid

We have synthesized various amide derivatives of benzodifuran-2-carboxylic acid from resorcinol. Reaction of 7-hydroxy-4-methylcoumarin with chloroacetone in anhydrous K2CO3 and dry acetone gave ether derivative of 7-hydroxy-4-methyl

Studies in synthesis of new psoralenamines

(Chemical Equation Presented) New amino psoralen derivatives have been synthesized via bromination. Bromination of 3,5-substituted psoralens has been studied. The second position of the furan ring is more susceptible to bromination than the α-position of

Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors

Three series of functionalized coumarin compounds were designed and prepared as cholinesterase (AChE and BuChE) inhibitors. The biological profile against AChE and BuChE of the prepared compounds was determined. Compound 7b exhibited a mixed-type of AChE

Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: Synthesis and photoreactivity

A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8- Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

Synthesis and evaluation of coumarin α-methylene-γ-butyrolactones: A new class of platelet aggregation inhibitors

In a search for new inhibitors of platelet aggregation, certain coumarin-hearing α-methylene-γ-butyrolactones were synthesized and evaluated for inhibitory activity against thrombin (Thr)-, arachidonic acid (AA)-, collagen (Col)-, and platelet-activating

POLYMER-SUPPORTED REAGENTS: AN EFFICIENT METHOD FOR THE SYNTHESIS OF PHENOXYACETONES

Phenoxides supported on Amberlite IRA-400 reacted with chloroacetone to give the corresponding phenoxyacetones in high yields and purity.

5'-Aminoalkyl-4',4-dialkylpsoralens

The invention relates to 5'-aminoalkyl-4',4-dialkylpsoralens having enhanced photosensitizing activity, especially oral activity, including early onset, increased maximum, and rapid decline, as well as low toxicity, when compared with psoralens of different structure.