275727

5-Methoxypsoralen

99%

• Synonym(s): 4-Methoxyfuro[3,2-g]benzopyrane-7-one, Bergapten, Geralen, Heraclin, Majudin
• Empirical Formula (Hill Notation): C₁₂H₈O₄
• CAS Number: 484-20-8
• Molecular Weight: 216.19
• UNSPSC Code: 12352103
• NACRES: NA.23
• PubChem Substance ID: 24856667
• EC Number: 207-604-5
• Beilstein/REAXYS Number: 19560
• MDL number: MFCD00010272

Properties

• Quality Segment: 200
• assay: 99%
• mp: 190-193 °C (lit.)
• SMILES string: COc1c2C=CC(=O)Oc2cc3occc13
• InChI: 1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
• InChI key: BGEBZHIAGXMEMV-UHFFFAOYSA-N

Description

General description

5-Methoxypsoralen (Bergapten) is a high-purity furanocoumarin derivative utilized primarily as a reference standard and photo-reactive probe in advanced biochemical research. At 99% purity, this compound is optimized for studying the mechanisms of photo-activation and nucleic acid intercalation. Its well-defined chemical profile makes it a foundational tool for laboratories investigating the interactions between small molecules, ultraviolet radiation, and cellular pathways.

Application

5-Methoxypsoralen has been studied for its use in oral photochemotherapy in the treatment of psoriasis and other skin diseases.

Features and Benefits

• Analytical Grade Purity: A minimum assay of 99% ensures high reproducibility and minimizes interference in sensitive analytical assays or high-throughput screening.
• Photo-Reactive Versatility: Serves as a critical reagent for experimental models involving light-induced biological responses, including studies on DNA cross-linking and enzymatic inhibition.
• Characterized Standards: Supported by rigorous quality control protocols (HPLC/NMR), providing researchers with the precision required for kinetic and structural studies.
• Analytical Standardization & Green Chemistry: Serves as a high-purity (99%) reference standard for calibrating HPLC/MS equipment and validating more sustainable extraction methodologies, such as Supercritical Fluid Extraction (SFE).
• Enzyme Kinetics & Signaling: Utilized as a biochemical probe to study acetylcholinesterase (AChE) inhibition and the modulation of cytokine signaling pathways (specifically TNF- and IL-6) in cellular models.
• Photo-Reactive Material Science: Investigated for the development of light-activated nanocarriers and photo-responsive polymers for precision-targeted molecular delivery research.
• In Vitro Metabolic Modeling: Employed in laboratory assays to investigate the chemical pathways of adipogenesis and the regulation of lipid accumulation within experimental cell lines.
• Molecular Interaction Studies: Used to analyze the kinetics of nucleic acid intercalation and the structural dynamics of covalent bonding in furanocoumarin-DNA research.
• Biocatalysis Research: Applied as a substrate in studies involving enzyme-catalyzed transformations to explore more eco-friendly chemical synthesis routes.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H317,H341,H351
• pcodes: P202 - P261 - P272 - P280 - P302 + P352 - P308 + P313
• Hazard Classifications: Carc. 2 - Muta. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges