14643-66-4

Basic information

• Product Name: COPROPORPHYRIN III DIHYDROCHLORIDE
• Synonyms: COPROPORPHYRIN III DIHYDROCHLORIDE;3,8,13,17-TETRAMETHYL-21H,23H-PORPHINE-2,7,12, 18-TETRAPROPIONIC ACID DIHYDROCHLORIDE;coproporphyriniii2HCl;Coproporphyrin Ⅲ dihydrochloride;3,8,13,17-tetramethylporphyrin-2,7,12,18-tetrapropanoic acid;Coproporphyrin dihydrochloride;2,7,12,18-Tetramethyl-21H,23H-porphyrin-3,8,13,17-tetrapropionic acid;CoproporphyrinIII Dihyrochloride
• CAS NO: 14643-66-4
• Molecular Formula: C₃₆H₃₈N₄O₈
• Molecular Weight: 727.63
• EINECS: 273-142-6
• Product Categories: Natural Porphyrins and Derivitives;Porphyrins;porphine (porphyrin) ligand
• Mol File: 14643-66-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 1258 °C at 760 mmHg
• Flash Point: 714.6 °C
• Appearance: purple/crystal
• Density: 1.366 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly, Sonicated), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: COPROPORPHYRIN III DIHYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: COPROPORPHYRIN III DIHYDROCHLORIDE(14643-66-4)
• EPA Substance Registry System: COPROPORPHYRIN III DIHYDROCHLORIDE(14643-66-4)

Safety Data

• Hazardous Substances Data: 14643-66-4(Hazardous Substances Data)

Usage

Description

COPROPORPHYRIN III DIHYDROCHLORIDE is a chemical compound derived from the porphyrin family, which is an essential component in various biological processes, including heme synthesis and energy production. It is characterized by its unique molecular structure and properties, making it a valuable compound for research and potential applications in different fields.

Uses

Used in Environmental Toxicity Assessment:
COPROPORPHYRIN III DIHYDROCHLORIDE is used as a biomarker for assessing environmental toxicity. It helps in identifying the presence of harmful substances in the environment and their potential impact on living organisms.
Used in Autism Research:
COPROPORPHYRIN III DIHYDROCHLORIDE is used as a biomarker for studying the susceptibility and underlying mechanisms of autism spectrum disorders. It aids in understanding the genetic and environmental factors that contribute to the development of autism and can potentially lead to the development of targeted therapies and interventions.
Used in Pharmaceutical Industry:
COPROPORPHYRIN III DIHYDROCHLORIDE is used as an active pharmaceutical ingredient for the development of drugs targeting various medical conditions. Its unique properties and interactions with biological systems make it a promising candidate for drug discovery and therapeutic applications.
Used in Diagnostics:
COPROPORPHYRIN III DIHYDROCHLORIDE is used as a diagnostic tool in the detection and monitoring of certain diseases and conditions. Its ability to interact with specific biological targets allows for the development of sensitive and specific diagnostic assays and tests.
Used in Research and Development:
COPROPORPHYRIN III DIHYDROCHLORIDE is used as a research compound for studying various biological processes and mechanisms. It serves as a valuable tool in the development of new therapies, understanding disease pathways, and advancing our knowledge of biochemistry and molecular biology.

InChI:InChI=1/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h13-16,38,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-

Upstream product

• 121992-23-2 [5-bromo-3-(2-carboxy-ethyl)-4-methyl-pyrrol-2-yl]-[5-bromo-3-(2-carboxy-ethyl)-4-methyl-pyrrol-2-ylidene]-methane; hydrobromide 
• 2624-63-7 coproporphyrinogen III 
• 1266113-13-6 5-methoxy-3-(2-methoxyacetyl)levulinic acid 
• 130895-64-6 1,5-dimethoxy-3-methyl-2,4-pentanedione 
• 34463-53-1 2-formyl-3-<2-(methoxycarbonyl)ethyl>-4-methylpyrrole 
• 132281-87-9 3-(2-FORMYL-4-METHYL-1H-PYRROL-3-YL)-PROPIONIC ACID 
• 872535-45-0 3-(2-hydroxymethyl-4-methyl-1H-pyrrol-3-yl)-propionic acid 
• 37531-58-1 [5-bromo-3-(2-carboxy-ethyl)-4-methyl-pyrrol-2-yl]-[4-(2-carboxy-ethyl)-3,5-dimethyl-pyrrol-2-ylidene]-methane; hydrobromide 

Downstream Products

• 2624-63-7 coproporphyrinogen III 
• 30783-27-8 3-vinyl-2,7,12,18-tetramethylporphyrin-8,13,17-tripropionic acid 
• 553-12-8 protoporphyrin IX 

Relevant articles and documents

Intermediates in the biosynthesis of porphyrins from porphobilinogen by Rhodopseudomonas spheroides.

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Noncanonical coproporphyrin-dependent bacterial heme biosynthesis pathway that does not use protoporphyrin

It has been generally accepted that biosynthesis of protoheme (heme) uses a common set of core metabolic intermediates that includes protoporphyrin. Herein, we show that the Actinobacteria and Firmicutes (high-GC and low-GC Gram-positive bacteria) are unable to synthesize protoporphyrin. Instead, they oxidize coproporphyrinogen to coproporphyrin, insert ferrous iron to make Fecoproporphyrin (coproheme), and then decarboxylate coproheme to generate protoheme. This pathway is specified by three genes named hemY, hemH, and hemQ. The analysis of 982 representative prokaryotic genomes is consistent with this pathway being the most ancient heme synthesis pathway in the Eubacteria. Our results identifying a previously unknown branch of tetrapyrrole synthesis support a significant shift from current models for the evolution of bacterial heme and chlorophyll synthesis. Because some organisms that possess this coproporphyrin-dependent branch are major causes of human disease, HemQ is a novel pharmacological target of significant therapeutic relevance, particularly given high rates of antimicrobial resistance among these pathogens.

The oxygen-independent coproporphyrinogen III oxidase HemN utilizes harderoporphyrinogen as a reaction intermediate during conversion of coproporphyrinogen III to protoporphyrinogen IX

During heme biosynthesis the oxygen-independent coproporphyrinogen III oxidase HemN catalyzes the oxidative decarboxylation of the two propionate side chains on rings A and B of coproporphyrinogen III to the corresponding vinyl groups to yield protoporphyrinogen IX. Here, the sequence of the two decarboxylation steps during HemN catalysis was investigated. A reaction intermediate of HemN activity was isolated by HPLC analysis and identified as monovinyltripropionic acid porphyrin by mass spectrometry. This monovinylic reaction intermediate exhibited identical chromatographic behavior during HPLC analysis as harderoporphyrin (3-vinyl-8,13,17-tripropionic acid-2,7,12,18- tetramethylporphyrin). Furthermore, HemN was able to utilize chemically synthesized harderoporphyrinogen as substrate and converted it to protoporphyrinogen IX. These results suggest that during HemN catalysis the propionate side chain of ring A of coproporphyrinogen III is decarboxylated prior to that of ring B. by Walter de Gruyter.

Biosynthesis of Porphyrins and Related Macrocycles. Part 15. Chemical and Enzymic Formation of Uroporphyrinogen Isomers from Unrearranged Aminomethylpyrromethane: Separation of Isomeric Coproporphyrin Esters

The unrearranged pyrromethane (1) is transformed chemically mainly into uro'gen-I with a smaller amount of uro'gen-IV but only traces of uro'gen-III are formed.Uro'gen-I is produced via a tetrapyrrolic (bilane) intermediate and when the diaminase-cosynthetase enzyme system from Euglena gracilis is present, this intermediate is converted into uro'gen-III.The rearrangement step for this conversion has the same characteristics found earlier for the natural biosynthetic process from porphobilinogen.Pyrromethane (1) is not a direct biosynthetic precursor of uro'gen-III and reasons are advanced why this is understandable.Methods are developed based on high pressure liquid chromatography for the separation of all four isomeric coproporphyrin esters.