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D7783 Sigma-Aldrich

Pyrroloquinoline quinone

≥95.0% (HPLC)

Synonym: 4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, Methoxatin, PQQ

  • CAS Number 72909-34-3

  • Empirical Formula (Hill Notation) C14H6N2O8

  • Molecular Weight 330.21

  •  Beilstein/REAXYS Number 3596812

  •  MDL number MFCD00043125

  •  PubChem Substance ID 24894162

  •  NACRES NA.79

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Properties

Related Categories Biochemicals and Reagents, Cofactors, Enzymes, Inhibitors, and Substrates, Oxidation-Reduction
Quality Level   200
biological source   synthetic
assay   ≥95.0% (HPLC)
form   powder
application(s)   HPLC: suitable
color   red to deep red
storage temp.   2-8°C
SMILES string   OC(=O)c1cc(C(O)=O)c-2c(n1)C(=O)C(=O)c3cc([nH]c-23)C(O)=O
InChI   1S/C14H6N2O8/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/h1-2,15H,(H,19,20)(H,21,22)(H,23,24)
InChI key   MMXZSJMASHPLLR-UHFFFAOYSA-N

Description

General description

Pyrroloquinoline Quinone (PQQ), also referred as methoxatin, is a water soluble orthoquinone molecule with redox-cycling ability.

Novel o-quinone coenzyme found in bacterial dehydrogenases and oxidases.

Application

Pyrroloquinoline quinone has been used:
• as a component of nanocurcumin formulation (NCF), to study its therapeutic effect on ameliorate hypoxia-induced stress in hypertrophied cardiomyocytes
• as a standard in fluorescence analysis
• to test its efficiency in suppressing restrained oxidative stress and hepatic fibrogenesis in mouse models

Biochem/physiol Actions

Pyrroloquinoline Quinone (PQQ) plays a vital role in gluconic acid production and biosynthesis by microbes. It acts as an effective microbial growth stimulant and biological control determinant for plant pathogens. PQQ also acts as an anti-melanogenic agent and is used to treat disorders related to hyper pigmentation. It exhibits diverse role in metabolism and cell signaling pathways. PQQ is used as a potential therapeutic to treat liver fibrosis.

PQQ is present in nanomolar quantities in most foods and in most animal tissuse. It promotes growth, mitochondrial function, and development in vivo and stimulates cell proliferation and viability in culture. It is a potent antioxidant that scavenges superoxide and peroxinitrite. It is neuroprotectant against 6-hydroxydopamine-induced and hypoxia/ischemia-induced neurotoxicity. PQQ conjugates to α-synuclein in vitro, inhibiting the formation of amyloid fibrils.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D7783.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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