51589-12-9

Basic information

• Product Name: protoporphyrin
• CAS NO: 51589-12-9
• Molecular Weight: 654.806
• Mol File: 51589-12-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: protoporphyrin(CAS DataBase Reference)
• NIST Chemistry Reference: protoporphyrin(51589-12-9)
• EPA Substance Registry System: protoporphyrin(51589-12-9)

Safety Data

• Hazardous Substances Data: 51589-12-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 5522-66-7 protoporphyrin IX dimethyl ester 
• 100-66-3 methoxybenzene 
• 14459-29-1 hematoporphyrin 

Downstream Products

• 5522-66-7 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 
• 31444-62-9 2,4-di(α-methoxyethyl)deuteroporphyrin IX 
• 142230-12-4 3-{(1Z,4Z,9Z,15Z)-7,12-Bis-(1-methoxy-ethyl)-3,8,13,17-tetramethyl-18-[2-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienylmethoxycarbonyl)-ethyl]-porphyrin-2-yl}-propionic acid 2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienylmethyl ester 
• 142230-13-5 C₆₀H₇₀N₄O₁₀ 
• 142230-09-9 C₅₈H₆₈N₆O₁₀ 
• 142230-08-8 C₅₈H₆₆N₄O₁₀S₂ 

Relevant articles and documents

Natural Tetrapyrrol Derivatives for the Photodynamic Therapy, 2. - Model Reactions for Direct C-C Linkages of Porphyrins

Until now, there is a lack of information about the structure of the active components in the diagnosis and photodynamic therapy of cancer with hematoporphyrin derivatives (HPD).We describe the formation of HPD in terms of benzyl cation chemistry.Selective formation of the C-C-linked model compounds 4, 5 by reaction of protoporphyrin dimethyl ester (2) with electron-rich aromatic compounds as well as of 9-12, 15-17, obtained by reaction of the porphyrin dimethyl esters 2, 6, 7, and 8 with carbon electrophiles (preformed Mannich salts), results from this concept. K ey Words: Photodynamic therapy (PDT) / Porphyrins / Hematoporphyrin derivative (HPD) / Mannich bases / Benzyl cations

Mechanism of a Novel Synthesis of Haemin c from Protohaemin and L-Cysteine. A Markownikoff-type Radical Addition Reaction

As a simulation of in vivo sulphide bond formation of c-type cytochromes, haemin c (4) was synthesized by the reaction of iron protoporphyrin IX with sodium borohydride in the presence of L-cysteine, oxygen, and cetyltrimethylammonium bromide (CTAB).When L-cysteine was omitted from the reaction mixture, mesohaemin (9) and haematohaemin (5) were obtained.The inhibitory effect of cyanide anion or carbon monoxide, as well as the inability of protoporphyrin (8) to serve in place of (3) in both reactions, indicated that the iron of (3) and oxygen were crucial in a primary process to give a common intermediate (11) for (4), (5), and (9).Trapping of (11) with oxygen indicated that it is the α-carbon radical of the 2- or 4-ethyl group derived from (3).The addition of deuterium (from sodium borodeuteride) to the β-carbon of the vinyl group of (3) and the resulting formation of (11) strongly suggested the intermediacy of a free hydrogen atom, which was generated in the reduction of (3) with sodium borohydride.The generation of a free hydrogen atom was also supported by a transfer experiment.