6054-10-0

Basic information

• Product Name: 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2
• Synonyms: 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2;6-Methoxy-8,8-dimethyl-2H,8H-benzo[1,2-b:3,4-b']dipyran-2-one;Braylin
• CAS NO: 6054-10-0
• Molecular Formula: C15H14O4
• Molecular Weight: 258.26926
• Mol File: 6054-10-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 133-135 °C
• Boiling Point: 441.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.225±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2(CAS DataBase Reference)
• NIST Chemistry Reference: 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2(6054-10-0)
• EPA Substance Registry System: 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2(6054-10-0)

Safety Data

• Hazardous Substances Data: 6054-10-0(Hazardous Substances Data)

Usage

General Description

2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2, also known as benzodipyran, is a chemical compound with a molecular formula of C16H10O2. This aromatic compound is composed of two fused pyran rings and is commonly used in the production of dyes, pigments, and antioxidants. It possesses fluorescent properties, making it useful for applications in fluorescence microscopy and labeling. Benzodipyran has also been studied for its potential as a photodynamic therapy agent for cancer treatment, as its light activation can generate reactive oxygen species to induce cell death in tumors. Additionally, it has shown promise as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. Overall, the unique structure and functional properties of 2H, 8H-Benzo[1,2-b:3,4-b']dipyran-2 make it a versatile and important chemical in various industrial and scientific fields.

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Relevant articles and documents

Synthesis and evaluation of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one derivatives as vasorelaxing agents

A series of substituted 8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-ones (chromeno-coumarin hybrids) was synthesized from scopoletin (11) as vasorelaxing agents. The synthesized compounds 21a-f, 22, 23a-e and scopoletin (11) were evaluated for vasorelaxation in endothelium intact rat main mesenteric artery (MMA). Compounds 11, 21a, 21c-f and 22 showed significant vasorelaxation in precontracted MMA within the range of EC50 value 1.58–5.02 μM. These derivatives presented 29.40–70.89 fold increased sensitivity for experimental tissue compared to scopoletin (11), the parent molecule. Among others, 22 was found to be the most active compound which had EC50 1.58 μM with 70.89 fold increased sensitivity. The mechanistic evaluation of 22 showed that it exerted vasorelaxation through Ca2+-activated K+ (BKca) channel and the effect was endothelium-independent.

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.