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
• Description: Pyrroloquinoline quinone (PQQ) is a novel biofactor for which a proposition can be made for physiological importance. PQQ was first recognized as an enzyme cofactor in bacteria. It has recently been tentatively identified as a component of interstellar dust. Thus, PQQ may have been present throughout early biological conception and evolution. PQQ is also a potent plant growth factor. Consequently, for animals and humans, there has been constant exposure to PQQ. In animals, PQQ is reported to participate in a range of biological functions with apparent survival benefits (e.g., improved neonatal growth and reproductive performance). There are also benefits from PQQ supplementation related to cognitive, immune, and antioxidant functions, as well as protection from cardiac and neurological ischemic events. Although PQQ is not currently viewed as a vitamin, its involvement in cell signaling pathways, particularly those important to mitochondriogenesis in experimental animal models, may eventually provide a rationale for defining PQQ as vital to life. For humans, such evidence suggests there may be similar parallels or benefits from improving PQQ status.
• Uses: Pyrroloquinoline quinone is an important growth factor for the body and a redox/cofactor found in a a class of enzymes called quinoproteins. It is a cofactor of microbial quinoprotein enzyme, and imidazopyrroline. it regulates the level of free radicals in the body, protects the body; anti-oxidative damage; enhances mitochondrial function; detoxification; disease, etc.

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:

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

diphenyldisulfane

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

C₁₈H₁₃N₃O₇

Refernces

• 1、 Lumpe, Henning,Daumann, Lena J.. "Studies of Redox Cofactor Pyrroloquinoline Quinone and Its Interaction with Lanthanides(III) and Calcium(II)". . p. 8432 - 8441. Retrieved 2019.
• 2、 RoseFigura, Jordan M.,Ehringer, Sandra,Schwarzenbacher, Robert,Toyama, Hirohide,Klinman, Judith P.. "Characterization of a protein-generated O2 binding pocket in PqqC, a cofactorless oxidase catalyzing the final step in PQQ production". . p. 1556 - 1566. Retrieved 2011.
• 3、 -. "Preparation method for synthesizing pyrroloquinoline quinone by five-step method". . . Retrieved 2020/05/01.
• 4、 -. "Pyrroloquinoline quinone synthetic method". Paragraph 0116-0117. . Retrieved 2018/05/07.