87345-22-0

Basic information

• Product Name: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin
• Synonyms: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin;Phenol, 4-(10,15,20-triphenyl-21H,23H-porphin-5-yl)- 4-(10,15,20-triphenylporphyrin-5-yl)phenol;5-(4-hydroxyphenyl)-10,15,20-triphenyl porphine
• CAS NO: 87345-22-0
• Molecular Formula: C₄₄H₃₀N₄O
• Molecular Weight: 630.74
• Mol File: 87345-22-0.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• Density: 1.29g/cm³
• Refractive Index: 1.709
• CAS DataBase Reference: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin(87345-22-0)
• EPA Substance Registry System: 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin(87345-22-0)

Safety Data

• Hazardous Substances Data: 87345-22-0(Hazardous Substances Data)

Usage

General Description

5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is a chemical compound that belongs to the porphyrin family. It is a synthetic derivative of naturally occurring porphyrins, which are tetrapyrrole macrocyclic compounds that play important roles in biological processes such as oxygen transport and enzyme catalysis. This specific compound contains a central porphyrin core with three phenyl groups attached at the 5, 10, and 15 positions, and a 4-hydroxyphenyl group at the 20 position. Porphyrins have been extensively studied for their potential applications in various fields including medicine, biology, and materials science, due to their unique photophysical and photochemical properties. 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin is particularly interesting for its potential use in photodynamic therapy, imaging, and sensing applications.

InChI:InChI=1/C44H30N4O/c49-32-18-16-31(17-19-32)44-39-26-24-37(47-39)42(29-12-6-2-7-13-29)35-22-20-33(45-35)41(28-10-4-1-5-11-28)34-21-23-36(46-34)43(30-14-8-3-9-15-30)38-25-27-40(44)48-38/h1-27,45,48-49H/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-

Upstream product

• 109-97-7 pyrrole 
• 100-52-7 benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 99522-34-6 4-[(tetrahydro-2H-pyran-2-yl)oxy]iodobenzene 
• 67066-09-5 5-bromo-10,20-dihexyl-15-phenylporphyrin (5) 
• 107798-98-1 5-phenyldipyrromethane 

Downstream Products

• 102202-48-2 5-(4-bromotetramethyleneoxyphenyl)-10,15,20-triphenylporphine 
• 88147-09-5 5-(4-hexadecyloxyphenyl)-10,15,20-triphenylporphine 

Relevant articles and documents

Selective synthesis and biological activity of triazine-porphyrins as potential anti-cancer agents

Ten new triazine-porphyrin derivatives were synthesized using a simple one-pot procedure from the reaction of tetraphenylporphyrin bearing a hydroxyl group with 2,4,6-trichloro-1,3,5-triazine, and then with amines or alcohols. The structures of the products were characterized by 1H NMR, LC/MS, UV-vis and elemental analysis. The cytotoxic activity of the triazine-porphyrin derivatives was evaluated in vitro against MCF-7 cell. All new compounds showed similar activity against MCF-7 cells in the absence of light when compared to 5-fluorouracil and hematoporphyrin.

Intramolecular Electron Transfer in Donor-Acceptor Systems. Porphyrins Bearing Trinitroaryl Acceptor Group

Porphyrins bearing picryl group in ortho, meta, and para positions of one of the mesoaryl groups of tetraphenylporphyrin (TPP) have been synthesized in the free-base form.The metal derivatives of the free-base picrylporphyrins (PPc) have been prepared.The broadened Soret absorption, the decreased optical absorbance values of Q bands, and the reduced singlet emission quantun yields of PPc indicate the existence of intramolecular interaction.The extent of this interaction is found to be greater than those observed for the intermolecular systems and varies with the position at which the picryl moiety is attached to the porphyrin as ortho > meta > para.The energies of the redox states, E(CT) of P+Pc-, calculated from the electrochemical redox potentials depend on the nature of the metal ion as free-base PPc > CuPPc > ZnPPc.The nature of intramolecular interaction between the picryl moiety and porphyrin unit is essentially ?-? (CT).Conclusive evidence for light-induced electron transfer in ZnPPc is presented from EPR studies.The decay profiles of the EPR signals vary with the position of the picryl moiety as ortho para meta.Computer simulation of structures substantiated by the 1H NMR results point out the restricted conformational freedom of the picryl moiety in ZnPPc.Arguments based on symmetry considerations of HOMO of the excited singlet state PPc and LUMO of picryl group indicate plane-to-plane orientation of the donor and acceptor in the picrylporphyrins.

Red Light-Triggered Intracellular Carbon Monoxide Release Enables Selective Eradication of MRSA Infection

Carbon monoxide (CO) is an important gaseous signaling molecule. The use of CO-releasing molecules such as metal carbonyls enables the elucidation of the pleiotropic functions of CO. Although metal carbonyls show a broad-spectrum antimicrobial activity, i

Synthesis and photophysical properties of novel pyrene-metalloporphyrin dendritic systems

A novel series of dendronized porphyrins bearing pyrene units in the periphery (Porph-O-Gn) and their metal complexes (M-[Porph-O-Gn]) are reported. The pyrene-containing Frechet-type dendrons up to the first generation were synthesized and further reacted with 5-phenol-10,15,20-triphenylporphyrin via an esterification reaction to afford the desired pyrene-labeled dendronized porphyrins. Later, these compounds were used as ligands to produce the corresponding complexes of Zn2+, Cu2+, Mg2+ and Mn3+. With the compounds in hand, the optical and photophysical properties of the dendritic metalloporphyrins were studied by absorption and fluorescence spectroscopy. The quantum yields, F?rster radius and efficiency of energy transfer were determined and discussed as a function of the structure and the donor-acceptor distances, finding an efficient energy transfer from the pyrene moiety to the metallated porphyrin core in each case.