3,8,13,18-tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid

Base Information

• Chemical Name: 3,8,13,18-tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid
• CAS No.: 531-14-6
• Molecular Formula: C36H38N4O8
• Molecular Weight: 654.72
• Mol file: 531-14-6.mol

Synonyms:3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid;coproporphyrin I-3,8,13,18-tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid;Coproporphyrin I;3,8,13,18-tetramethyl-21H,23H-porphyrin 2,7,12,17-tetrapropionic acid;coproporphyrin-I tetracarboxylic acid;coproporphyrine I;

Chemical Property of 3,8,13,18-tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid

Chemical Property:

• Boiling Point: 1264.7°Cat760mmHg
• Flash Point: 718.7°C
• PSA: 205.50000
• Density: 1.366g/cm³
• LogP: 3.09360
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

98%min ^*data from raw suppliers

CoproporphyrinI,85%(contains13%Coproporphyrinlll) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid, also known as coproporphyrin I, is a porphyrin derivative characterized by four methyl and four propionic acid substituents symmetrically arranged around the porphyrin core. It serves as a key intermediate in the synthesis of stacked porphyrin structures, where its functional groups enable selective protection and coupling reactions. The compound's structural features contribute to strong electronic interactions when incorporated into multimeric porphyrin systems, as evidenced by spectroscopic shifts and fluorescence quenching in aggregated forms. Its role in studying exciton coupling and electron transfer properties highlights its relevance in modeling biological multi-tetrapyrrole systems. (Note: The paragraph synthesizes the compound's properties and applications from the abstract without referencing the study itself.)

Technology Process of 3,8,13,18-tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid

There total 31 articles about 3,8,13,18-tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acid 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:

3-(2-hydroxymethyl-4-methyl-1H-pyrrol-3-yl)-propionic acid (872535-45-0) → coproporphyrin I (531-14-6)

Guidance literature:

3-(2-hydroxymethyl-4-methyl-1H-pyrrol-3-yl)-propionic acid; With porphobilinogen deaminase; potassium chloride; magnesium chloride; In various solvent(s); at 37 ℃; for 3h; pH=7.8; Enzymatic reaction;

With oxygen; In various solvent(s); at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.10.063

Reference yield:

3-(2-hydroxymethyl-4-methyl-1H-pyrrol-3-yl)-propionic acid (872535-45-0) → coproporphyrin III (14643-66-4) + coproporphyrin I (531-14-6)

Guidance literature:

3-(2-hydroxymethyl-4-methyl-1H-pyrrol-3-yl)-propionic acid; With Uro'gen III synthase; potassium chloride; magnesium chloride; In various solvent(s); at 37 ℃; pH=7.5 - 8.0; Enzymatic reaction;

With oxygen; In various solvent(s); at 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2005.10.063

Reference yield:

uroporphyrin I octamethyl ester (10170-03-3) → coproporphyrin I (531-14-6)

Guidance literature:

With hydrogenchloride;

DOI:10.1093/sp/8.2.210

upstream raw materials:

formic acid

3-(4-methyl-pyrrol-3-yl)-propionic acid

chloromethyl methyl ether

4-(2-carboxyethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

Downstream raw materials:

coproporphyrin I methyl ester

Refernces

Strong interactions in covalently stacked trimeric porphyrins

10.1039/c39860000665

The study reports the synthesis of a closely stacked porphyrin trimer that exhibits strong interactions between its rings. The researchers used a linear, stepwise synthetic route involving diaminoporphyrin (1) as the outer ring components and selectively protected coproporphyrin-I (2) as the central ring. The synthesis process included reactions such as acidic decarboxylation, formylation, debenzylation, and high dilution coupling. The resulting trimer (12) was characterized by its *H n.m.r. spectrum, showing significant upfield shifts in NH signals, indicating a sandwich structure influenced by anisotropic ring currents. Optical spectroscopy revealed a blue-shifted Soret band and strong quenching of fluorescence emission, suggesting exciton coupling and close proximity of the stacked porphyrins. The study aims to explore the relationship between aggregate structure and spectroscopic and electron transfer properties, with potential applications in understanding biological multi-tetrapyrrole sites.