156006-10-9

Basic information

• Product Name: 3,4-dimethyl-7-(2-oxopropoxy)-2H-chromen-2-one
• Synonyms: 2H-1-benzopyran-2-one, 3,4-dimethyl-7-(2-oxopropoxy)-
• CAS NO: 156006-10-9
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.2586
• Mol File: 156006-10-9.mol

Chemical Properties

• Boiling Point: 412.3°C at 760 mmHg
• Flash Point: 184.8°C
• Density: 1.188g/cm³
• Vapor Pressure: 5.25E-07mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 3,4-dimethyl-7-(2-oxopropoxy)-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dimethyl-7-(2-oxopropoxy)-2H-chromen-2-one(156006-10-9)
• EPA Substance Registry System: 3,4-dimethyl-7-(2-oxopropoxy)-2H-chromen-2-one(156006-10-9)

Safety Data

• Hazardous Substances Data: 156006-10-9(Hazardous Substances Data)

Upstream product

• 108-46-3 recorcinol 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 2107-78-0 3,4-dimethyl-7-hydroxycoumarin 
• 78-95-5 chloroacetone 

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.

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 characterization of new methylpsoralens as potential photochemotherapeutic agents

Three new psoralens with methyl groups on carbons involved in their reactive double bonds (compounds 9-11 in Scheme 1) were synthesized from the corresponding 7-hydroxycoumarins by cyclization of acetonyl derivatives of the latter in an alkaline medium. In preliminary tests, the new methyl-substituted psoralens exhibited considerable interaction in the dark with DNA, good photoreactivity against the macromolecule, and also interesting antiproliferative activity.