D7783
Pyrroloquinoline quinone
≥95.0% (HPLC)
Synonym(s):
4,5-Dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, Methoxatin, PQQ
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About This Item
Empirical Formula (Hill Notation):
C14H6N2O8
CAS Number:
Molecular Weight:
330.21
UNSPSC Code:
12352106
NACRES:
NA.79
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3596812
biological source
synthetic
Quality Level
assay
≥95.0% (HPLC)
form
powder
technique(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
Related Categories
General description
Novel o-quinone coenzyme found in bacterial dehydrogenases and oxidases.
Pyrroloquinoline Quinone (PQQ), also referred as methoxatin, is a water soluble orthoquinone molecule with redox-cycling ability.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Crystal structure of PqqB from Pseudomonas putida at 2.2
Metlitzky M, et al.
Journal of biophysical chemistry, 3(02), 206-206 (2012)
Nanocurcumin--pyrroloquinoline formulation prevents hypertrophy--induced pathological damage by relieving mitochondrial stress in cardiomyocytes under hypoxic conditions
Nehra S, et al.
Experimental & Molecular Medicine, 49(12), e404-e404 (2017)
J A Duine
European journal of biochemistry, 200(2), 271-284 (1991-09-01)
The presently best known and largest group of quinoproteins consists of enzymes using the cofactor 2,7,9-tricarboxy-1H-pyrrolo[2,3-f]quinoline- 4,5-dione (PQQ), a compound having a pyrrole ring fused to a quinoline ring with an o-quinone group in it. Representatives of this group are
Jiro Omata et al.
JPEN. Journal of parenteral and enteral nutrition, 35(5), 616-624 (2011-04-22)
Experimental intravenous (IV) parenteral nutrition (PN) diminishes gut-associated lymphoid tissue (GALT) cell number and function. PN solution cannot maintain GALT at the same level as a normal diet, even when delivered intragastrically (IG). Previous studies demonstrated pyrroloquinoline quinone (PQQ)-deficient mice
Pyrroloquinoline quinone (PQQ) from methanol dehydrogenase and tryptophan tryptophylquinone (TTQ) from methylamine dehydrogenase.
V L Davidson
Advances in protein chemistry, 58, 95-140 (2001-10-23)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| D7783-10MG | 04061833588888 |
| D7783-5MG | 04061833270530 |
| D7783-1MG | 04061833588895 |
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