42059-79-0

Basic information

• Product Name: 6-METHOXY-4-OXO-4H-CHROMENE-3-CARBALDEHYDE
• Synonyms: 6-Methoxychromone-3-carboxaldehyde;4-keto-6-methoxy-chromene-3-carbaldehyde;6-methoxy-4-oxo-3-chromenecarboxaldehyde;6-methoxy-4-oxo-chromene-3-carbaldehyde;6-methoxy-4-oxochromene-3-carbaldehyde;6-METHOXY-3-FORMYLCHROMONE;6-METHOXY-4-OXO-4H-CHROMENE-3-CARBALDEHYDE;AKOS BBS-00001402
• CAS NO: 42059-79-0
• Molecular Formula: C₁₁H₈O₄
• Molecular Weight: 204.18
• Mol File: 42059-79-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 162-166°C
• Boiling Point: 365.2°Cat760mmHg
• Flash Point: 165.2°C
• Appearance: /
• Density: 1.401g/cm³
• Vapor Pressure: 1.6E-05mmHg at 25°C
• Refractive Index: 1.648
• CAS DataBase Reference: 6-METHOXY-4-OXO-4H-CHROMENE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-4-OXO-4H-CHROMENE-3-CARBALDEHYDE(42059-79-0)
• EPA Substance Registry System: 6-METHOXY-4-OXO-4H-CHROMENE-3-CARBALDEHYDE(42059-79-0)

Safety Data

• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 42059-79-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 30, p. 3553, 1974 DOI: 10.1016/S0040-4020(01)97034-6

InChI:InChI=1/C11H8O4/c1-14-8-2-3-10-9(4-8)11(13)7(5-12)6-15-10/h2-6H,1H3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 1200-06-2 4-methoxyphenyl acetate 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 79-37-8 oxalyl dichloride 
• 68-12-2 N,N-dimethyl-formamide 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 4998-50-9 (2-hydroxy-5-methoxyphenyl)(p-tolyl)methanone 

Relevant articles and documents

Design and synthesis of chromone-nitrogen mustard derivatives and evaluation of anti-breast cancer activity

Chromone has emerged as one of the most important synthetic scaffolds for antitumor activity, which promotes the development of candidate drugs with better activity. In this study, a series of nitrogen mustard derivatives of chromone were designed and syn

Discovery of Novel Chromone Derivatives Containing a Sulfonamide Moiety as Anti-ToCV Agents through the Tomato Chlorosis Virus Coat Protein-Oriented Screening Method

A number of novel chromone derivatives containing sulfonamide moieties were designed and synthesized, and the activity of compounds against tomato chlorosis virus (ToCV) was assessed using the ToCVCP-oriented screening method. Comparative molecular field analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA) models were established based on the dissociation constant (Kd) values of the target compounds, and compound 35 was designed and synthesized with the aid of CoMFA and CoMSIA models. The study of affinity interaction indicated that compound 35 exhibited excellent affinity with ToCVCP with a Kd value of 0.11 μM, which was better than that of the positive control agents xiangcaoliusuobingmi (0.44 μM) and ningnanmycin (0.79 μM). In addition, the in vivo inhibitory effect of compound 35 on the ToCVCP gene was evaluated by the quantitative real-time polymerase chain reaction. ToCVCP gene expression levels of the compound 35 treatment group were reduced by 67.2%, which was better than that of the positive control agent ningnanmycin (59.5%). Therefore, compound 35 can be used as a potential anti-ToCV drug in the future.

Synthesis and biological evaluation of chromone-3-carboxamides

The aim of our study was to synthesize novel chromone-3-carboxamides and to conduct biological evaluations in search for lead compounds for the treatment of a range of debilitating disease states. Corresponding 2-hydroxyacetophenones were subjected to Vilsmeier-Haack formylation to give chromone-3-carbaldehydes, which were subsequently oxidised to give chromone-3-carboxylic acids. Treatment of the carboxylic acids with thionyl chloride resulted in the in situ formation of the corresponding acid chlorides, which were reacted with various amines in the presence of triethylamine to give the corresponding novel chromone-3-carboxamides in good yields. Selected chromone derivatives were then evaluated for their anti-inflammatory, anti-tryponosomal and cytotoxic properties.