5452-39-1

Basic information

• Product Name: 3-ACETYL-8-METHOXY-CHROMEN-2-ONE
• Synonyms: RARECHEM AB KA K008;3-ACETYL-8-METHOXY-CHROMEN-2-ONE;3-ACETYL-8-METHOXYCOUMARIN;CHEMBRDG-BB 5557338;3-ACETYL-8-METHOXY-2H-CHROMEN-2-ONE;3-ethanoyl-8-methoxy-chromen-2-one;3-acetyl-8-methoxy-2H-chromen-2-one(SALTDATA: FREE);8-Methoxy-3-acetylcouMarin
• CAS NO: 5452-39-1
• Molecular Formula: C₁₂H₁₀O₄
• Molecular Weight: 218.21
• Mol File: 5452-39-1.mol
• Article Data: 47

Chemical Properties

• Boiling Point: 439.6°C at 760 mmHg
• Flash Point: 200.5°C
• Appearance: /
• Density: 1.281g/cm³
• Vapor Pressure: 6.3E-08mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 3-ACETYL-8-METHOXY-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-ACETYL-8-METHOXY-CHROMEN-2-ONE(5452-39-1)
• EPA Substance Registry System: 3-ACETYL-8-METHOXY-CHROMEN-2-ONE(5452-39-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 5452-39-1(Hazardous Substances Data)

Usage

General Description

3-acetyl-8-methoxy-chromen-2-one is a chemical compound with the molecular formula C13H10O4. It is a derivative of chromenone, a naturally occurring compound found in various plants. 3-acetyl-8-methoxy-chromen-2-one possesses antioxidant and anti-inflammatory properties, and has been studied for its potential therapeutic effects. It has also been investigated for its potential use as a drug candidate for treating various diseases and conditions, including cancer. 3-acetyl-8-methoxy-chromen-2-one is of interest to researchers and scientists for its diverse pharmacological activities and potential applications in medicine and drug development.

InChI:InChI=1/C12H10O4/c1-7(13)9-6-8-4-3-5-10(15-2)11(8)16-12(9)14/h3-6H,1-2H3

Upstream product

• 141-97-9 ethyl acetoacetate 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 5977-14-0 acetoacetamido 
• 102-01-2 N-phenylacetoacetamide 
• 700-44-7 6-methoxysalicylaldehyde 
• 6186-89-6 ethyl methyl malonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 
• 13664-26-1 2-hydroxy-3-methoxybenzylideneimine 

Downstream Products

• 116317-06-7 3-[2-(3,5-Dimethyl-4-phenylazo-pyrazol-1-yl)-thiazol-4-yl]-8-methoxy-chromen-2-one 
• 1419179-72-8 8-methoxy-3-(5-(2-hydroxybenzoyl)pyridin-2-yl)coumarin 
• 1419179-73-9 8-methoxy-3-(5-(2-hydroxy-5-methylbenzoyl)pyridin-2-yl)coumarin 
• 1419179-74-0 8-methoxy-3-(5-(5-chloro-2-hydroxybenzoyl)pyridin-2-yl)coumarin 
• 1365411-57-9 C₂₆H₁₉ClN₄O₃ 

Relevant articles and documents

Synthesis of Chromeno[4′,3′:4,5]pyrido[1,2- a ]pyrazines and -diazepines by the Reaction of Substituted 2-(3-Acetyl-2-oxo-2 H -chromen-4-yl)fumarates with 1, n -Diamines

A two-step sequence was developed for the synthesis of chromeno[4′,3′:4,5]pyrido[1,2- a ]pyrazine-13-carboxylates and -diazepine-14-carboxylates by the reaction of substituted dimethyl 2-(3-acetyl-2-oxo-2 H -chromen-4-yl)fumarates with 1, n -diamines at room temperature. Advantages of this protocol include ease of handling and the absence of a metal catalyst.

Design, synthesis, antioxidant and anticancer activity of new coumarin derivatives linked with thiazole, isoxazole or pyrazole moiety

Background: Three new series of coumarin derivatives 4a-e, 6a-d and 7a-d were synthesized and characterized by elemental analyses and spectral data including 2D NMR. All compounds 4a-e, 6a-d and 7a-d were evaluated for their in vitro antioxidant and antic

3-Acetyl-8-methoxy-2[H]-chromen-2-one derived Schiff bases as potent antiproliferative agents: Insight into the influence of 4(N)-substituents on the in vitro biological activity

A series of 3-acetyl-8-methoxycoumarin appended thiosemicarbazones (1–4) was prepared from the reaction of 3-acetyl-8-methoxycoumarin with 4(N)-substituted thiosemicarbazides in a view of ascertaining their biological properties with the change of N-terminal substitution in the thiosemicarbazide moiety. Comprehensive characterization was brought about by various spectral and analytical methods. The molecular structures of all the compounds were determined by single crystal X-ray diffraction analysis. Binding studies with Calf thymus DNA (CT-DNA) and proteins such as Bovine Serum Albumin (BSA) and Human Serum Albumin (HSA) indicated an intercalative mode of binding with DNA and static quenching mechanism with proteins. The compounds cleaved plasmid DNA (pBR322) and acted well as free radical scavengers. A good spectrum of antimicrobial activity was observed against four bacterial and five fungal pathogens. The compounds exhibited profound antiproliferative activity on MCF-7 (human breast cancer) and A549 (human lung carcinoma) cell lines. Assay on human normal keratinocyte cell line HaCaT showed that the compounds were non-toxic to normal cells.

One-pot synthesis of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives

An efficient synthetic procedure for the preparation of novel (E)-3-(3,8a-dihydro-2H-oxazolo[3,2-a]pyridin-2-ylidene)chroman-2-one derivatives was developed. A sequential one-pot, two-step tandem reaction starting from 3-(2-bromoacetyl)-2H-chromen-2-one derivatives synthesized, pyridine, and naphthols in the presence of triethylamine proceeded smoothly in acetonitrile under reflux conditions. In this process, 2-oxo-2H-chromen-3-yl)ethyl)pyridinium bromide derivatives as intermediate produced in situ, followed by Michael addition of naphthoxide anion and intramolecular cylization, resulted the corresponding products in good to high yields. All of the compounds were obtained in high purity without any use of more purification.

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.