Trioxsalen

Base Information

• Chemical Name: Trioxsalen
• CAS No.: 3902-71-4
• Molecular Formula: C14H12O3
• Molecular Weight: 228.247
• Hs Code.: 29322985
• European Community (EC) Number: 223-459-0
• NSC Number: 757371,71047
• UNII: Y6UY8OV51T
• DSSTox Substance ID: DTXSID3023716
• Nikkaji Number: J3.411H
• Wikipedia: Trioxsalen
• Wikidata: Q854263
• NCI Thesaurus Code: C66640
• Pharos Ligand ID: 92UQ9WMQ4CL4
• Metabolomics Workbench ID: 43620
• ChEMBL ID: CHEMBL1475
• Mol file: 3902-71-4.mol

Synonyms:2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-one;4,5',8-Trimethylpsoralen;NSC 71047;NSC-71047;NSC71047;Trimethylpsoralen;Trioxisalenum;Trioxsalen;Trioxysalen;Trisoralen

Chemical Property of Trioxsalen

Chemical Property:

• Appearance/Colour: White to slightly beige crystalline powder
• Melting Point: 229-231 °C(lit.)
• Refractive Index: 1.5557 (estimate)
• Boiling Point: 389 °C at 760 mmHg
• Flash Point: 189.1 °C
• PSA: 43.35000
• Density: 1.236 g/cm³
• LogP: 3.46440
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 228.078644241
• Heavy Atom Count: 17
• Complexity: 374

Purity/Quality:

99% ^*data from raw suppliers

Trioxysalen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-40
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
• Uses: melanizing agent, antipsoriatic Trioxsalen has been used: to induce small deletion mutations in worms in combination with ultraviolet A (UVA) to induce interstrand crosslinks (ICLs) in DNA for the preparation and photoactivation of trimethyl psoralen
• Indications: Trioxsalen (Trisoralen) followed by UVA exposure is used to repigment vitiliginous areas and in photochemotherapy.

Technology Process of Trioxsalen

There total 6 articles about Trioxsalen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

→ trioxsalen (3902-71-4)

Guidance literature:

Reference yield: 60.0%

4,8-dimethyl-7-<(β-bromoallyl)oxy>coumarin (72478-66-1) → trioxsalen (3902-71-4)

Guidance literature:

With N,N-diethylaniline; at 225 ℃; for 24h;

DOI:10.1021/jo01292a045

Reference yield: 14.0%

4,8-dimethyl-7-<(β-chloroalllyl)oxy>coumarin (69897-63-8) → trioxsalen (3902-71-4)

Guidance literature:

With N,N-diethylaniline; at 220 - 225 ℃; for 24h;

DOI:10.1021/jo01292a045

upstream raw materials:

4,8-dimethyl-7-<(β-chloroalllyl)oxy>coumarin

6-allyl-7-hydroxy-4,8-dimethyl-2H-chromen-2-one

4,8-dimethyl-7-<(β-bromoallyl)oxy>coumarin

4,8-dimethyl-7-hydroxycoumarin

Downstream raw materials:

4'-N-Phthalimidomethyl-4,5',8-trimethylpsoralen

4'-(4-amino-2-oxa)butyl-4,5',8-trimethylpsoralen Hydrochloride

4-(<β-hydroxyethoxy>methyl)-4,5',8-trimethylpsoralen

4'-chloromethyl-4,5',8-trimethylpsoralen

Refernces

Dopamine/serotonin receptor ligands. 13¹: Homologization of a benzindoloazecine-type dopamine receptor antagonist modulates the affinities for dopamine D₁-D₅ receptors

10.1021/jm060213k

The research focuses on the synthesis and evaluation of dopamine receptor antagonists based on the benzindoloazecine structure. The study aimed to modulate the affinities for dopamine D1-D5 receptors by homologizing a lead compound, LE 300. Two homologue antagonists were synthesized, and their affinities and inhibitory activities at D1-D5 receptors were measured using radioligand binding experiments and a functional Ca2+ assay. The phenylpropyl homologue 3 showed superior selectivity and affinity for the D5 subtype with a Ki of 0.6 nM, while the indolylpropyl homologue 2 exhibited decreased affinity for all subtypes. The experiments involved the synthesis of compounds 2 and 3 through a series of chemical reactions, including the use of tryptamine, lactone 15, and various reagents such as PCl5, POCl3, and NaBH4. The synthesized compounds were then tested for their binding affinities and inhibitory activities, with the results indicating significant differences in receptor affinities between the two homologues. The analyses used included radioligand binding studies and a calcium fluorescence assay to determine the inhibitory activity of the compounds at the dopamine receptors.