7249-34-5

Basic information

• Product Name: 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone
• CAS NO: 7249-34-5
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.3805
• Mol File: 7249-34-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 592.2°C at 760 mmHg
• Flash Point: 212°C
• Density: 1.326g/cm³
• Vapor Pressure: 1.27E-14mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone(7249-34-5)
• EPA Substance Registry System: 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone(7249-34-5)

Safety Data

• Hazardous Substances Data: 7249-34-5(Hazardous Substances Data)

Usage

Molecular Structure

2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone is a derivative of cyclopentanone with two benzylidene groups, each attached to a hydroxy and a methoxy group.

Reactivity

The presence of hydroxy and methoxy groups makes the compound highly reactive, making it a potential precursor for the synthesis of various organic molecules and polymers.

Antioxidant Properties

The presence of phenolic groups in the compound indicates potential antioxidant properties, which could have implications in the development of pharmaceuticals or health supplements.

Potential Applications

Due to its unique structure and properties, 2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone has potential applications in the fields of medicine and materials science.

Upstream product

• 121-33-5 vanillin 
• 120-92-3 cyclopentanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 946161-27-9 C₃₁H₃₆O₇ 
• 91471-08-8 3-methoxy-4-(tetrahydropyran-2-yloxy)benzaldehyde 

Downstream Products

• 834912-92-4 2,5-bis(4-acetoxy-3-methoxybenzylidene)cyclopentanone 
• 51728-79-1 2,5-divanillyl-cyclopentanone 

Relevant articles and documents

Vanillin-derived epoxy monomer for synthesis of bio-based epoxy thermosets: effect of functionality on thermal, mechanical, chemical and structural properties

Abstract: Tri-functional vanillin-derived epoxy monomer was developed through the synthesized di-functional reagent and cured with a series of different types of hardeners (hydroxyl and amine based) to evaluate thermo-mechanical properties of the resultan

Inhibition of dengue virus by curcuminoids

The dengue virus is considered to be a globally important human pathogen prevalent in tropical and subtropical regions of the world. According to a recent estimate, the disease burden due to DENV infections is ～390 million infections per year globally in ～100 countries including the southern US, Puerto Rico and Hawaii, resulting in nearly ～25,000 deaths mostly among children. Despite the significant morbidity and mortality that results from DENV infections, there is currently no effective chemotherapeutic treatment for DENV infections. We identified curcumin as an inhibitor of DENV2 NS2B/NS3protease in a previous high-throughput screening (HTS) campaign. We synthesized four analogues of curcumin (curcuminoids) and tested the in vitro protease inhibition activity and inhibition of replication by cell-based assays. The results revealed that curcumin is a weak inhibitor of the viral protease. However, the analogues exhibited more potent inhibition of DENV infectivity in plaque assays suggesting that the cellular pathway(s) required for viral replication and/or assembly are targeted by these compounds. Further analysis shows that inhibition of genes involved in lipid biosynthesis, and of actin polymerization by curcuminoids, are likely to be involved as their mode of action in DENV2-infected cells. Three of the curcumin derivatives possess good selectivity indices (SI) (>10) when compared to the parent curcumin.

Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway

Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/β-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of β-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of β-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than 1a (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma.