2624-63-7

Basic information

• Product Name: Coproporphyrinogen III
• Synonyms: Coproporphyrinogen III;2,7,12,18-Tetrakis(3-oxo-3-hydroxypropyl)-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydro-21H,23H-porphyrin;5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-porphyrin-2,7,12,18-tetrapropanoic acid;5,10,15,20,22,24-Hexahydrocoproporphyrin III
• CAS NO: 2624-63-7
• Molecular Formula: C₃₆H₄₄N₄O₈
• Molecular Weight: 660.75656
• Mol File: 2624-63-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 961°Cat760mmHg
• Flash Point: 535°C
• Appearance: /
• Density: 1.358g/cm³
• PKA: 4.70±0.10(Predicted)
• CAS DataBase Reference: Coproporphyrinogen III(CAS DataBase Reference)
• NIST Chemistry Reference: Coproporphyrinogen III(2624-63-7)
• EPA Substance Registry System: Coproporphyrinogen III(2624-63-7)

Safety Data

• Hazardous Substances Data: 2624-63-7(Hazardous Substances Data)

Usage

General Description

Coproporphyrinogen III is a chemical compound that plays a crucial role in the process of heme biosynthesis, which is essential for the formation of hemoglobin and other heme-containing proteins. It is an intermediate in the biosynthetic pathway of heme, a vital component of hemoglobin that carries oxygen in the blood. Coproporphyrinogen III is the substrate for the enzyme coproporphyrinogen oxidase, which catalyzes the formation of protoporphyrinogen IX, another crucial intermediate in the heme biosynthetic pathway. In addition to its role in heme biosynthesis, coproporphyrinogen III has been implicated in certain porphyria diseases, which are a group of disorders characterized by abnormalities in heme metabolism. Understanding the functions and metabolism of coproporphyrinogen III is important for the development of treatments for porphyria and other heme-related disorders.

Upstream product

• 14643-66-4 coproporphyrin-III 
• 74839-16-0 tert-butyl 3,4'-bis<β-(methoxycarbonyl)ethyl>-4,3'-dimethyl-5'-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate 
• 4792-10-3 3-{5-Formyl-2-[5-formyl-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrol-2-ylmethyl]-4-methyl-1H-pyrrol-3-yl}-propionic acid methyl ester 
• 809-27-8 4,4'-bis-(2-methoxycarbonyl-ethyl)-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid 
• 99602-83-2 13,17-bis(2-benzyloxycarbonylethyl)-8-(2-carboxyethyl)-3-(2-methoxycarbonylethyl)-2,7,12,18-tetramethylporphin 
• 99602-82-1 13,17-bis(2-benzyloxycarbonylethyl)-3-(2-carboxyethyl)-8-(2-methoxycarbonylethyl)-2,7,12,18-tetramethylporphin 
• 99602-78-5 C₃₁H₃₈N₂O₈ 
• 99602-71-8 5,5'-diformyl-3,3'-bis(2-benzyloxycarbonylethyl)-4,4'-dimethyl-2,2'-methylenedipyrrole 
• 99602-72-9 t-butyl 5'-carboxy-3,4'-bis(2-methoxycarbonylethyl)-3',4-dimethyl-2,2'-methylenedipyrrole-5-carboxylate 
• 99602-79-6 t-butyl 5-carboxy-3-(2-methoxycarbonylethyl)-4'-(2-carboxyethyl)-3',4-dimethyl-2,2'-methylenedipyrrole-5'-carboxylate 
• 99602-81-0 C₂₀H₂₄N₂O₈ 
• 99602-67-2 benzyl 5-acetoxymethyl-4-(2-benzyloxycarbonylethyl)-3-methylpyrrole-2-carboxylate 
• 72562-25-5 t-butyl 3-(2-carboxyethyl)-4-methylpyrrole-2-carboxylate 
• 51742-43-9 benzyl 3-(2-benzyloxycarbonylethyl)-4-methylpyrrole-2-carboxylate 

Downstream Products

• 42607-18-1 harderoporphyrinogen-III 
• 7412-77-3 harderoporphyrinogen IX 
• 30783-27-8 3-vinyl-2,7,12,18-tetramethylporphyrin-8,13,17-tripropionic acid 
• 553-12-8 protoporphyrin IX 
• 14643-66-4 coproporphyrin-III 
• 39010-85-0 iron-coproporphyrin III 
• 927179-10-0 heme b 
• 42607-17-0 8,13,17-tris(2-methoxycarbonylethyl)-2,7,12,18-tetramethyl-3-vinylporphyrin 
• 5522-66-7 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 
• 5522-63-4 coproporphyrin III tetramethyl ester 

Relevant articles and documents

Direct assay of enzymes in heme biosynthesis for the detection of porphyrias by tandem mass spectrometry. Uroporphyrinogen decarboxylase and coproporphyrinogen III oxidase

We report new assays of enzymes uroporphyrinogen decarboxylase (UROD) and coproporphyrinogen III oxidase (CPO) in the heme biosynthetic pathway. The assays were developed for use in clinical diagnostics of inherited disorders porphyria cutanea tarda and hereditary coproporphyria, respectively. Electrospray ionization tandem mass spectrometry is used to monitor the decarboxylation of pentaporphyrinogen I or uroporphyrinogen III catalyzed by UROD and to determine the enzyme activity in human erythrocytes by measuring the production of coproporphyrinogen I or III. The Km value for pentaporphyrinogen I was measured as 0.17 ± 0.03 μM. A mass spectrometric assay was also developed for the two-step decarboxylative oxidation of coproporphyrinogen III to protoporphyrinogen IX catalyzed by CPO in mitochondria from human lymphocytes (Km = 0.066 ± 0.009 μM). The assays show good reproducibility, use simple workup by liquid-liquid extraction of enzymatic products, and employ commercially available substrates and internal standards.

Handling heme: The mechanisms underlying the movement of heme within and between cells

Heme is an essential cofactor and signaling molecule required for virtually all aerobic life. However, excess heme is cytotoxic. Therefore, heme must be safely transported and trafficked from the site of synthesis in the mitochondria or uptake at the cell surface, to hemoproteins in most subcellular compartments. While heme synthesis and degradation are relatively well characterized, little is known about how heme is trafficked and transported throughout the cell. Herein, we review eukaryotic heme transport, trafficking, and mobilization, with a focus on factors that regulate bioavailable heme. We also highlight the role of gasotransmitters and small molecules in heme mobilization and bioavailability, and heme trafficking at the host-pathogen interface.

Biosynthesis of Porphyrins and Related Macrocycles. Part 25. Synthesis of Analogues of Coproporphyrinogen-III and Studies of their Interaction with Copropophyrinogen-III Oxidase from Euglena gracilis

Analogues of coproporphyrinogen-III have been synthesized in which the propionate groups respectively on ring-A and on ring-B are modified either by homologation or esterification.Coproporphyrinogen-III oxidase from Euglena gracilis acts on the analogues which possess normal substituents on ring-A to generate a vinyl group on that ring.The enzyme does not affect the analogues in which the ring-A propionate group has been changed.Conditions have been defined for the MacDonald synthesis of porphyrins which yield products of high isomeric purity.