pyrroloquinoline quinone

Names

[ Name ]:
pyrroloquinoline quinone

[Synonym ]:
MFCD00043125
coenzyme PQQ
2,7,9-Tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione
PQQ Cofactor
Pyrroloquinoline-quinone
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
4,5-dihydro-4,5-dioxo-1H-pyrrolo-[2,3-f]quinoline-2,7,9-tricarboxylic acid
1H-Pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
methoxanthin
4,5-Dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
PQQ
Pyrroloquinoline quinone
2,7,9-Tricarboxy-4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline
Methoxatin
1H-Pyrrolo[2,3-f]quinolin-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-
1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid, 4,5-dihydro-4,5-dioxo-

Biological Activity

[Description]:

Pyrroloquinoline quinone (PQQ), a redox co-factor, is an anionic, redox-cycling orthoquinone. Pyrroloquinoline quinone is isolated from cultures of methylotropic bacteria and tissues of mammals. Pyrroloquinoline quinone is an essential nutrient for mammals and is important for immune function[1][2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

Human Endogenous Metabolite

[In Vitro]

Mouse pups born to and nursing from Pyrroloquinoline quinone (PQQ)-deprived dams have a compromised immune response as well as alopecia, a hunched posture, and a susceptibility to aortic aneurysms[2].

[References]

[1]. Moog RS, et al. Evidence for methoxatin (pyrroloquinolinequinone) as the cofactor in bovine plasma amine oxidase from resonance Raman spectroscopy. Proc Natl Acad Sci U S A. 1986 Nov;83(22):8435-9.

[2]. Bishop A, et al. Methoxatin (PQQ) in guinea-pig neutrophils. Free Radic Biol Med. 1994 Oct;17(4):311-20.

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
1018.6±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₄H₆N₂O₈

[ Molecular Weight ]:
330.206

[ Flash Point ]:
569.8±34.3 °C

[ Exact Mass ]:
330.012421

[ PSA ]:
174.72000

[ LogP ]:
-0.65

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.801

[ Storage condition ]:
2-8°C

[ Stability ]:
Light and Temperature Sensitive

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Molecular-level characterization of elastin-like constructs and human aortic elastin

Matrix Biol. 38 , 12-21, (2014)

This study aimed to characterize the structures of two elastin-like constructs, one composed of a cross-linked elastin-like polypeptide and the other one of cross-linked tropoelastin, and native aorti...

Genome-wide RNA sequencing analysis of quorum sensing-controlled regulons in the plant-associated Burkholderia glumae PG1 strain.

Appl. Environ. Microbiol. 81 , 7993-8007, (2015)

Burkholderia glumae PG1 is a soil-associated motile plant-pathogenic bacterium possessing a cell density-dependent regulation system called quorum sensing (QS). Its genome contains three genes, here d...

Pyrroloquinoline-quinone suppresses liver fibrogenesis in mice.

PLoS ONE 10(3) , e0121939, (2015)

Liver fibrosis represents the consequences of a sustained wound healing response to chronic liver injuries, and its progression toward cirrhosis is the major cause of liver-related morbidity and morta...