Temoporfin

Base Information

• Chemical Name: Temoporfin
• CAS No.: 122341-38-2
• Molecular Formula: C₄₄H₃₂N₄O₄
• Molecular Weight: 680.762
• Mol file: 122341-38-2.mol

Synonyms:3,3',3'',3'''-(7,8-Dihydroporphyrin-5,10,15,20-tetrayl)tetraphenol;5,10,15,20-Tetra(m-hydroxyphenyl)chlorin;5,10,15,20-Tetrakis(m-hydroxyphenyl)chlorin;8-Dihydroporphyrin-5;EF 9;Foscan;Fosgel;Foslip;Fospeg;mTHPC;

Chemical Property of Temoporfin

Chemical Property:

• Melting Point: >250 °C
• Refractive Index: 1.734
• PSA: 137.22000
• Density: 1.386 g/cm³
• LogP: 5.91260
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Temoporfin,~90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Temoporfin (mTHPC) is a second-generation photosensitizer used in photodynamic therapy (PDT), known for its amphiphilic properties and efficacy in targeting tumors. It belongs to the chlorin class, specifically as a derivative of 5,10,15,20-tetrakis(m-hydroxyphenyl)chlorin, and has been modified to optimize its localization and photodynamic activity. The compound's structure allows for mixed hydrophilic/hydrophobic substitution patterns, enhancing its suitability for PDT applications. Research has focused on synthesizing related porphyrins to improve photosensitizer performance, leveraging methods like condensation and transition metal-catalyzed coupling. Temoporfin's derivatives are characterized for their potential in PDT, emphasizing their role in advancing therapeutic precision.

Technology Process of Temoporfin

There total 5 articles about Temoporfin 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: 60.0%

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine (22112-79-4) → temoporfin (122341-38-2)

Guidance literature:

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine; With toluene-4-sulfonic acid hydrazide; at 140 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; Inert atmosphere;

DOI:10.1002/chem.201304202

Reference yield:

methanol (67-56-1) + Temoporfin → Succinimide (123-56-8,89963-74-6) + methyl 3-hydroxybenzoate (19438-10-9) + temoporfin (122341-38-2) + 7,8-dihydro-1,9-bis(3-hydroxybenzoyl)-5-(3-hydroxyphenyl)pyrromethene

Guidance literature:

With air; In methanol; for 5.3h; Product distribution; Photolysis;

DOI:10.1021/ol025842c

Reference yield:

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine (22112-79-4) → temoporfin (122341-38-2) + Temoporfin

Guidance literature:

With potassium carbonate; toluene-4-sulfonic acid hydrazide; In 1,4-dioxane; at 120 ℃; for 0.416667h; Microwave irradiation; Sealed vessel;

DOI:10.1016/j.inoche.2009.12.032

upstream raw materials:

methanol

meso-5,10,15,20-tetra(3-hydroxyphenyl)porphine

meta-hydroxybenzaldehyde

Refernces

Lead structures for applications in photodynamic therapy. Part 1: Synthesis and variation of m-THPC (Temoporfin) related amphiphilic A₂BC-type porphyrins

10.1016/j.tet.2005.03.086

The research focuses on the synthesis and variation of m-THPC (Temoporfin) related amphiphilic A2BC-type porphyrins for applications in photodynamic therapy (PDT). The study explores the role of photosensitizer localization and aims to develop new photosensitizers by synthesizing unsymmetrically substituted tetrapyrroles with mixed hydrophilic/hydrophobic substitution patterns. The experiments involve the use of well-established condensation methods combined with functionalization via organolithium compounds or transition metal-catalyzed coupling protocols. Starting from simple A2- or AB-porphyrins, the researchers describe the synthesis of various A2B-, A3-, A3B-, and A2BC-porphyrins. The reactants include dipyrromethane, aldehydes, and organolithium reagents, while analyses are performed using techniques such as NMR, UV/vis spectroscopy, mass spectrometry, and elemental analysis to characterize the synthesized porphyrins and evaluate their potential as photosensitizers in PDT.