494-56-4

Basic information

• Product Name: [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE
• Synonyms: [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE;6,7-(Methylenedioxy)-2H-1-benzopyran-2-one;6,7-(Methylenedioxy)coumarin;6,7-Methylenedioxy-2H-1-benzopyran-2-one;6H-1,3-Dioxolo[4,5-g][1]benzopyran-6-one;Aiapin
• CAS NO: 494-56-4
• Molecular Formula: C₁₀H₆O₄
• Molecular Weight: 190.15224
• Mol File: 494-56-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 369.9°Cat760mmHg
• Flash Point: 169.5°C
• Appearance: /
• Density: 1.482g/cm³
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE(494-56-4)
• EPA Substance Registry System: [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE(494-56-4)

Safety Data

• Hazardous Substances Data: 494-56-4(Hazardous Substances Data)

Usage

Description

[1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE is a complex and systematic chemical compound that belongs to the class of chromenone compounds. These are fused heterocyclic compounds that contain a benzene ring fused to a pyran ring. This particular compound is unique due to an additional dioxolane ring fused to the pyran ring. Chromenone compounds are known for their various biological activities, such as anti-inflammatory, antibacterial, anticancer, and antioxidant properties. The specific properties and potential applications of [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE would depend on further research and testing, but its unique structure and potential biological activities make it an interesting compound for further study.

Uses

Used in Pharmaceutical Industry:
[1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE is used as a potential therapeutic agent for various medical conditions due to its potential biological activities. Its anti-inflammatory, antibacterial, anticancer, and antioxidant properties make it a promising candidate for the development of new drugs and treatments.
Used in Chemical Research:
[1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE is used as a subject of study in chemical research to better understand its properties, potential applications, and to explore its use in the development of new compounds with specific biological activities.
Used in Material Science:
The unique structure of [1,3]DIOXOLO[4,5-G]CHROMEN-6-ONE may also have potential applications in material science, where it could be used to develop new materials with specific properties based on its chemical and physical characteristics.

InChI:InChI=1/C10H6O4/c11-10-2-1-6-3-8-9(13-5-12-8)4-7(6)14-10/h1-4H,5H2

Upstream product

• 4720-68-7 4,5-methylenedioxy-2-hydroxybenzaldehyde 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 108-24-7 acetic anhydride 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 305-01-1 aesculetin 

Relevant articles and documents

Toward establishing structure-activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity.

Synthesis and structural revision of naturally occurring ayapin derivatives

The synthesis of three highly oxygenated naturally occurring coumarins, 8-methoxy-6,7-methylenedioxycoumarin, 5-methoxy-6,7-methylenedioxycoumarin and 5,8-dimethoxy-6,7-methylenedioxycoumarin is described for the first time, together with a new method for the preparation of ayapin (6,7- methylenedioxycoumarin). Comparison of the spectroscopic data of the synthetic tetraoxygenated coumarin 5,8-dimethoxy-6,7-methylenedioxycoumarin with literature reports resulted in the structural revision of several natural coumarins. Two coumarins, both identified as 5,8-dimethoxy-6,7- methylenedioxycoumarin must have other structures, while the structure of another coumarin, described as the isomeric 7,8-dimethoxy-5,6- methylenedioxycoumarin has to be revised to 5,8-dimethoxy-6,7- methylenedioxycoumarin.

A Convenient & Short Route for the Synthesis of Ayapin & Scoparone

A short, convenient and general route to synthesise two important intermediates in coumarin synthesis, viz. 2-hydroxy-4,5-methylenedioxybenzaldehyde (4a) and 2-hydroxy-4,5-dimethoxybenzaldehyde (4b), is described.These have been converted by Wittig reaction into the naturally occurring coumarins, ayapin (1a) and scoparone (1b), respectively.