Pyrroloquinoline quinone

Base Information

• Chemical Name: Pyrroloquinoline quinone
• CAS No.: 72909-34-3
• Deprecated CAS: 124716-23-0
• Molecular Formula: C14H6N2O8
• Molecular Weight: 330.21
• Hs Code.: 29339900
• European Community (EC) Number: 839-691-6
• UNII: 47819QGH5L
• DSSTox Substance ID: DTXSID3041162
• Nikkaji Number: J126.218A
• Wikipedia: Pyrroloquinoline_quinone
• Wikidata: Q414583
• Pharos Ligand ID: C9ZFRJLPHA5Y
• Metabolomics Workbench ID: 42459
• ChEMBL ID: CHEMBL1235421
• Mol file: 72909-34-3.mol

Synonyms:2,7,9-Tricarboxy-1H-Pyrrolo-(2,3-f)Quinoline-4,5-Dione;2,7,9-Tricarboxypyrroloquinoline Quinone;4,5-Dihydro-4,5-Dioxo-1-H-Pyrrolo(2,3-f)Quinoline-2,7,9-Tricarboxylic Acid;Coenzyme PQQ;Coenzyme, PQQ;Cofactor, PQQ;Methoxatin;PQQ Coenzyme;PQQ Cofactor;PQQ, Coenzyme;Pyrrolo Quinoline Quinone;Pyrrolo-Quinoline Quinone;Pyrroloquinoline Quinone;Quinone, Pyrrolo-Quinoline;Quinone, Pyrroloquinoline

Chemical Property of Pyrroloquinoline quinone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.801
• Boiling Point: 1018.6 °C at 760 mmHg
• PKA: 1.88±0.20(Predicted)
• Flash Point: 569.8 °C
• PSA: 174.72000
• Density: 1.963 g/cm³
• LogP: 0.55030
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 330.01241515
• Heavy Atom Count: 24
• Complexity: 647

Purity/Quality:

99% ^*data from raw suppliers

4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic Acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C2=C(C(=O)C(=O)C3=C2NC(=C3)C(=O)O)N=C1C(=O)O)C(=O)O
• General Description: Pyrroloquinoline quinone (PQQ), also known as methoxatin or coenzyme PQQ, is a redox-active cofactor found in microbial dehydrogenases, oxidases, and mammalian copper-containing amine oxidases. It features an o-quinone structure that serves as the active site for catalytic functions, playing a critical role in enzymatic redox reactions. The functional groups of PQQ, particularly its carboxyl moieties, are essential for its binding and activity in enzyme systems. Isotopically labeled PQQ derivatives have been synthesized to study its biosynthesis, redox mechanisms, and physiological roles, highlighting its importance in biochemical and biomedical research.

Technology Process of Pyrroloquinoline quinone

There total 84 articles about Pyrroloquinoline quinone 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: 100.0%

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate (74447-88-4) → pyrroloquinoline quinone (72909-34-3)

Guidance literature:

With sodium carbonate; In water; at 30 ℃; for 24h;

DOI:10.1246/bcsj.59.1911

Reference yield: 98.0%

5,5-Dimethoxy-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester (78939-40-9) → pyrroloquinoline quinone (72909-34-3)

Guidance literature:

With potassium carbonate; In water; at 85 ℃; for 4h;

DOI:10.1021/ja00408a067

Reference yield: 97.0%

4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester (80721-47-7) → pyrroloquinoline quinone (72909-34-3)

Guidance literature:

4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester; With lithium hydroxide; water; In tetrahydrofuran; at 0 - 17 ℃; for 31.5h;

With hydrogenchloride; potassium chloride; In tetrahydrofuran; water; at 0 ℃; for 1h; pH=5.3 - 6;

With sulfuric acid; In water; at 20 ℃; for 2.5h;

upstream raw materials:

trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate

4,5-Dihydro-4,5-dioxo-1H-pyrrolo<2,3-f>chinolin-2,7,9-tricarbonsaeure-(2-ethyl)(7,9-dimethyl)ester

5,5-Dimethoxy-4-oxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester

4,5-dihydroxy-4,5-dioxo-1H-pyrrolo{2,3-f}quinoline-2,7,9-tricarboxylic acid

Downstream raw materials:

C₂₁H₁₁N₃O₇

C₁₈H₁₃N₃O₇

4,5-dihydro-5-hydroxy-4-oxo-5-(2-oxopropyl)-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylic acid

(4-hydroxyphenyl)methanol

Refernces

SYNTHESIS OF (13)C- AND (2)H-LABELLED PQQ

10.1016/S0040-4039(00)82160-7

The study focuses on the synthesis of isotopically labeled pyrroloquinoline quinone (PQQ), a cofactor found in various microbial dehydrogenases, oxidases, and mammalian copper-containing amine oxidases. The researchers adopted and modified existing chemical synthesis schemes to prepare different isotopically labeled PQQ derivatives, such as 3-13C-PQQ, 3-2H-PQQ, and 8-2H-PQQ. The synthesis of 3-13C-PQQ and 3-2H-PQQ involved the Japp-Klingemann hydrazone synthesis, Fischer indolixation, and Doebner-Von Miller type condensation, using starting materials like methoxy-nitro-aniline and methyl-acetoacetate. For 8-2H-PQQ, a Pfitzinger quinoline synthesis was employed, starting from aminoindole and using reagents like isatin, pyruvic acid, and ceric ammonium nitrate. These isotopically labeled PQQ compounds are valuable for studying the biosynthesis, enzymatic redox catalysis, and physiological role of PQQ in different organisms.

Syntheses of pyrroloquinoline quinone derivatives: Model compounds of a novel coenzyme PQQ (methoxatin)

10.1055/s-1987-28172

The study focuses on the synthesis of pyrroloquinoline quinone (PQQ) derivatives as model compounds to investigate the roles of functional groups in the novel coenzyme PQQ. PQQ is a crucial coenzyme for various oxidoreductases, and its o-quinone structure is confirmed to be the active site for catalytic functions. The researchers synthesized several PQQ derivatives, including 2,7-dicarboxylic acid derivative (1e), 2,9-dicarboxylic acid derivative (1d), and 1-methylated derivative (1f), using intermediates such as trimethyl ester (5) and methyl ester (4). The synthesis processes involved various chemical reactions, including selective hydrolysis, decarboxylation, oxidation, and N-methylation. The synthesized compounds were characterized by melting points, IR spectra, and NMR spectra. The study aims to clarify the roles of the carboxyl groups and the binding mode of PQQ to enzyme active sites, which are essential for understanding the catalytic activity of PQQ.