79127-57-4

Basic information

• Product Name: 2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-diol
• Synonyms: 2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-diol;pyrroloquinoline quinol
• CAS NO: 79127-57-4
• Molecular Formula: C₁₄H₈N₂O₈
• Molecular Weight: 0
• Mol File: 79127-57-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 619.6°C at 760 mmHg
• Flash Point: 328.5°C
• Appearance: /
• Density: 2.07g/cm³
• Vapor Pressure: 3.25E-16mmHg at 25°C
• Refractive Index: 1.855
• CAS DataBase Reference: 2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-diol(79127-57-4)
• EPA Substance Registry System: 2,7,9-tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-diol(79127-57-4)

Safety Data

• Hazardous Substances Data: 79127-57-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A pyrroloquinoline having hydroxy groups at the 4- and 5-positions and carboxy groups at the 2-, 7- and 9-positions.

InChI:InChI=1/C14H8N2O8/c17-10-4-2-6(14(23)24)15-8(4)7-3(12(19)20)1-5(13(21)22)16-9(7)11(10)18/h1-2,15-16,19-20H,(H,21,22)(H,23,24)

Upstream product

• 52-90-4 L-Cysteine 
• 70-18-8 GLUTATHIONE 
• 33721-54-9 N-(2-methoxy-5-nitrophenyl)acetamide 
• 81770-66-3 4,5-dimethoxy-1H-pyrrolo<2,3-f>quinoline-2,7,9-tricarboxylic acid 
• 5965-53-7 diethyl 2-ketoglutarate 
• 67827-72-9 2-methoxy-5-nitroaniline hydrochloride 
• 72909-34-3 pyrroloquinoline quinone 
• 108-98-5 thiophenol 
• 996-19-0 aminoguanidine sulfate 
• 74447-88-4 trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate 

Downstream Products

• 115736-51-1 Cu(PQQH2)(bpy) 
• 72909-34-3 pyrroloquinoline quinone 

Relevant articles and documents

Chemical behavior of coenzyme PQQ toward aminoguanidine: Redox reaction and adduct formation

The reaction of coenzyme PQQ with aminoguanidine, which is known as an inhibitor of quinoprotein amine oxidases, was investigated in vitro. The redox reaction predominantly proceeded at pH 10.0 to give PQQH2 (quinol), whereas deactivation of PQQ occurred at pH 6.7 to give the triazine adduct. In the case of semicarbazide or acetohydrazide as the substrate, azo adduct formation was mainly observed even at pH 10.0. Importance of the C-5 carbinolamine-type intermediate a is discussed.

4,5-disubstituted-1-hydro-pyrrole(2,3-f)quinoline-2,7,9-tricarboxylate compound and application

The invention discloses a 4,5-disubstituted-1-hydro-pyrrole(2,3-f)quinoline-2,7,9-tricarboxylate compound and analogues or derivatives thereof. The structure of the compound is shown as a formula I, and the structural formula is as shown in the specification. In the formula, R1 and R4 are respectively and independently selected from the following atoms or groups: hydrogen, linear or branched C1-8 alkyl, deuterated linear or branched C1-8 alkyl, aralkyl or substituted aryl radical; R2 is independently selected from the following atoms or groups: halogen, linear or branched C1-8 alkoxy and deuterated linear or branched C1-8 alkoxy; and R3 is independently selected from the following atoms or groups: linear or branched C1-8 alkoxy and deuterated linear or branched C1-8 alkoxy. The compound can serve as a reaction intermediate for synthesizing PQQ (Pyrroloquinoline Quinone), and the oxidizing agent process adopting CAN in the PQQ synthesis in the conventional patent and literature is replaced. Therefore, the whole process is cheap and high-efficiency.

PRODUCTION METHOD OF REDUCED PYRROLOQUINOLINE QUINONE

An object of the present invention is to provide a method for conveniently producing reduced pyrroloquinoline quinone from oxidized pyrroloquinoline quinone without needing expensive equipment, and a method for stabilizing reduced pyrroloquinoline quinone. According to the present invention, high-quality reduced pyrroloquinoline quinone can be obtained conveniently and efficiently in a manner suitable for industrial-scale production by mixing pyrroloquinoline quinone and ascorbic acid in a solvent.