coproporphyrinogen III

Base Information

• Chemical Name: coproporphyrinogen III
• CAS No.: 2624-63-7
• Molecular Formula: C36H44 N4 O8
• Molecular Weight: 660.767
• DSSTox Substance ID: DTXSID40180875
• Nikkaji Number: J313.191B
• Wikipedia: Coproporphyrinogen_III
• Wikidata: Q2468481
• Metabolomics Workbench ID: 37689
• ChEMBL ID: CHEMBL1231891
• Mol file: 2624-63-7.mol

Synonyms:coproporphyrinogen III

Chemical Property of coproporphyrinogen III

Chemical Property:

• Boiling Point: 961°Cat760mmHg
• PKA: 4.70±0.10(Predicted)
• Flash Point: 535°C
• PSA: 212.36000
• Density: 1.358g/cm³
• LogP: 4.97800
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 12
• Exact Mass: 660.31591437
• Heavy Atom Count: 48
• Complexity: 1170

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2CC3=C(C(=C(N3)CC4=C(C(=C(N4)CC5=C(C(=C(N5)CC(=C1CCC(=O)O)N2)C)CCC(=O)O)C)CCC(=O)O)CCC(=O)O)C
• General Description: Coproporphyrinogen III is a tetrapyrrole macrocycle and a key intermediate in the biosynthesis of heme and other porphyrins, playing a vital role in bioenergetic processes. It can form abiotically from acyclic reactants, such as decarboxy analogues of d-aminolevulinic acid, under prebiotic conditions without requiring porphobilinogen (PBG) as an intermediate. This suggests a plausible non-enzymatic pathway for its formation, relevant to the origin of life and early metabolic systems.

Technology Process of coproporphyrinogen III

There total 34 articles about coproporphyrinogen III 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-{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 (4792-10-3) → coproporphyrinogen III (2624-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH₂Cl₂ / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min

2: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min

With potassium hydroxide; sodium amalgam; sodium acetate; trifluoroacetic acid; In methanol; dichloromethane;

Reference yield:

heptaprophyrinogen III (111980-20-2) → coproporphyrinogen III (2624-63-7)

Guidance literature:

heptaprophyrinogen III; With ethylenediaminetetraacetic acid; DL-dithiothreitol; uroporphyrinogen decarboxylase; In phosphate buffer; water; at 37 ℃; pH=6.8;

With ethylenediaminetetraacetic acid; DL-dithiothreitol; uroporphyrinogen decarboxylase; In phosphate buffer; water; at 37 ℃;

With ethylenediaminetetraacetic acid; DL-dithiothreitol; uroporphyrinogen decarboxylase; In phosphate buffer; water; at 37 ℃; Further stages.;

DOI:10.1021/ac702130n

Reference yield:

dibenzyl 3,3'-bis(2-methoxycarbonylethyl)-4,4'-dimethyl-2,2'-pyrromethane-5,5'-dicarboxylate (992-36-9) → coproporphyrinogen III (2624-63-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / H₂ / 10percent Pd/C / tetrahydrofuran

2: 60 percent / trimethyl orthoformate / trifluoroacetic acid / 0.37 h / 0 °C

3: 58 percent / 1.) trifluoroacetic acid, 2.) sodium acetate / methanol; CH₂Cl₂ / 1.) 2-3 deg C 90 min, 2.) 18 deg C 5 min, 3.) 50 min

4: 1.) 2M aq. potassium hydroxide; 2.) sodium amalgam / 1.) tetrahydrofuran 20 deg C; 2.) 3-4 min

With potassium hydroxide; sodium amalgam; hydrogen; sodium acetate; trifluoroacetic acid; trimethyl orthoformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; trifluoroacetic acid;

upstream raw materials:

coproporphyrin III tetramethyl ester

4-(2-methoxycarbonylethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate

benzyl 5-acetoxymethyl-4-(2-methoxycarbonylethyl)-3-methylpyrrole-2-carboxylate

Downstream raw materials:

harderoporphyrinogen-III

harderoporphyrinogen IX

3-vinyl-2,7,12,18-tetramethylporphyrin-8,13,17-tripropionic acid

protoporphyrin IX

Refernces

Abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants

10.1039/c0nj00716a

The research focuses on the abiotic formation of uroporphyrinogen and coproporphyrinogen from acyclic reactants, which are key precursors in the biosynthesis of tetrapyrrole macrocycles like porphyrins. These macrocycles are essential in various bioenergetic processes and are considered crucial for the origin of life. The study aimed to identify plausible prebiotic routes for forming these macrocycles, particularly addressing the challenge of forming the pyrrole precursor, porphobilinogen (PBG). The researchers successfully demonstrated a structure-directed route where d-aminolevulinic acid (ALA) reacts with 5-methoxy-3-(methoxyacetyl)levulinic acid (1-AcOH) under anaerobic conditions in water at moderate temperatures and pH levels, yielding uroporphyrinogen. This process bypasses the need for PBG, a significant hurdle in prebiotic chemistry, and suggests a possible prebiotic pathway for the formation of tetrapyrrole macrocycles. The study also showed that a different precursor could lead to the formation of coproporphyrinogen without the intermediacy of uroporphyrinogen. The chemicals used in this process include ALA, 1-AcOH, and their decarboxy analogues, which under specific conditions, resulted in the formation of uroporphyrinogen and coproporphyrinogen, respectively.