Pyrroloquinoline quinone (PQQ) - ≥98%(HPLC) , CAS No.72909-34-3

CAS: 72909-34-3 Cat. No.: D134423 Peso molecular: 330.21 Número EC: 839-691-6

GRADE & PURITY ≥98%(HPLC)

Synonyms

2,4,6-tricarboxylic-pyrrolo[2,3-5,6]quinoline 8,9-quinone | 2,7,9-Tricarboxy-1H-pyrrolo(2,3-f)quinoline-4,5-dione | 4,5-Dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylic acid | Pyrroloquinoline dione tricarboxylic acid | MFCD00043125 | PQQ;

Storage

Store at 2-8°C

Shipped In

Wet ice

Descripción general

Pyrroloquinoline quinone is a cofactor of microbial quinoprotein enzyme, and imidazopyrroline. A redox/cofactor found in a a class of enzymes called quinoproteins.
A redox/cofactor found in a a class of enzymes called quinoproteins

Product Application
Pyrroloquinoline quinone has been used in：
As a component of nanocurcumin preparation (NCF), the effect of NCF on hypoxic-induced stress of hypertrophic cardiomyocytes was studied；As a standard product for fluorescence detection；The inhibitory effects on oxidative stress and liver fibrosis in mouse models were examined

Specifications

Sinónimos

2, 4, 6-tricarboxylic-pyrrolo[2, 3-5, 6]quinoline 8, 9-quinone | 2, 7, 9-Tricarboxy-1H-pyrrolo(2, 3-f)quinoline-4, 5-dione | 4, 5-Dihydro-4, 5-dioxo-1H-pyrrolo(2, 3-f)quinoline-2, 7, 9-tricarboxylic acid | Pyrroloquinoline dione tricarboxylic acid | MFCD00043125 | PQQ;

Especificaciones y pureza

≥98%(HPLC)

Mecanismos bioquímicos y fisiológicos

Pyrroloquinoline quinone (PQQ) plays an important role in the production and biosynthesis of gluconic acid by microorganisms. It is an effective microbial growth promoter and a biocontrol determinant of plant pathogens. PQQ is an antimelanin-producing age

Condiciones de almacenamiento de almacenamiento

Store at 2-8°C

Enviado en

Wet ice

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%(HPLC)

Nombres e identificadores

• Pubchem Sid: 504750451
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750451
• Sonrisas canónicas: C1=C(C2=C(C(=O)C(=O)C3=C2NC(=C3)C(=O)O)N=C1C(=O)O)C(=O)O
• IUPAC Name: 4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid
• InChIKey: MMXZSJMASHPLLR-UHFFFAOYSA-N
• 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)
• Isómeros SMILES: C1=C(C2=C(C(=O)C(=O)C3=C2NC(=C3)C(=O)O)N=C1C(=O)O)C(=O)O
• Peso molecular: 330.21
• Reaxy-Rn: 3596812
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=3596812&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Quinolines and derivatives
      • Subclass Pyrroloquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Quinolines and derivatives
• Subclass: Pyrroloquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrroloquinoline quinones
• Alternative Parents: Quinoline carboxylic acids Tricarboxylic acids and derivatives Pyridinecarboxylic acids Indoles and derivatives Pyrrole 2-carboxylic acids Aryl ketones O-quinones Substituted pyrroles Vinylogous amides Heteroaromatic compounds Azacyclic compounds Carboxylic acids Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pyrroloquinoline quinone - Quinoline-4-carboxylic acid - Quinoline-2-carboxylic acid - Indole or derivatives - Pyridine carboxylic acid - Pyridine carboxylic acid or derivatives - Tricarboxylic acid or derivatives - O-quinone - Pyrrole-2-carboxylic acid - Pyrrole-2-carboxylic acid or derivatives - Aryl ketone - Quinone - Pyridine - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Vinylogous amide - Ketone - Azacycle - Carboxylic acid derivative - Carboxylic acid - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as pyrroloquinoline quinones. These are compounds with a structure based on the 2,7,-tricarboxy-1H-pyrrolo[2,3-f ]quinoline-4,5-dione. Pyrroloquinoline Quinones usually bear a carboxylic acid group at the C-2, C-7 and C-9 positions.
• External Descriptors: Prosthetic group [Fig]

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

GPR35 Tchem G-protein coupled receptor 35 (2 Activities)

Discover Target: GPR35

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MCF7 (126967 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HepG2 (196354 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mecanismos de acción

Propiedades químicas y físicas

• Sensibilidad: Heat sensitive
• Punto de fusión (°C): 150 °C
• Peso molecular: 330.210 g/mol
• XLogP3: -0.100
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 330.012 Da
• Monoisotopic Mass: 330.012 Da
• Topological Polar Surface Area: 175.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 647.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Yan Shi, Wei Xu, Dawei Ni, Wenli Zhang, Cuie Guang, Wanmeng Mu.  (2023)  Identification and application of a novel deoxynivalenol-degrading enzyme from Youhaiella tibetensis.  FOOD CHEMISTRY,      [PMID:37783127] [10.1016/j.foodchem.2023.137609]

2. Meng Du, Wei Chen, Chen Qian, Zhuo Chen, Guan-Lin Chen, Han-Qing Yu.  (2023)  Using Rayleigh Scattering to Correct the Inner Filter Effect of the Fluorescence Excitation–Emission Matrix.  ANALYTICAL CHEMISTRY,      [PMID:37556363] [10.1021/acs.analchem.3c01093]

3. Xiong Xiang, Amakye William Kwame, Yinglu Qing, Shan Li, Min Wang, Jiaoyan Ren.  (2023)  Natural antioxidants inhibit oxidative stress-induced changes in the morphology and motility of cells.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2023.102442]

4. Yan Zhang, Qiang Liu, Wei Ma, Hanxiao Liu, Jingwen Zhu, Likai Wang, Hongchang Pei, Qinze Liu, Jinshui Yao.  (2021)  Insight into the synergistic adsorption-reduction character of chromium(VI) onto poly(pyrogallol-tetraethylene pentamine) microsphere in synthetic wastewater.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:34839912] [10.1016/j.jcis.2021.11.086]

5. Fato Tano Patrice, Kaipei Qiu, Li-Jun Zhao, Essy Kouadio Fodjo, Da-Wei Li, Yi-Tao Long.  (2018)  Individual Modified Carbon Nanotube Collision for Electrocatalytic Oxidation of Hydrazine in Aqueous Solution.  ACS Applied Nano Materials,      [PMID:] [10.1021/acsanm.8b00018]

6. Fato Tano Patrice, Kaipei Qiu, Li-Jun Zhao, Essy Kouadio Fodjo, Da-Wei Li, Yi-Tao Long.  (2018)  Electrocatalytic Oxidation of Tris(2-carboxyethyl)phosphine at Pyrroloquinoline Quinone Modified Carbon Nanotube through Single Nanoparticle Collision.  ANALYTICAL CHEMISTRY,      [PMID:29701064] [10.1021/acs.analchem.7b05405]

7. Shanying Han, Tianyu Du, Hui Jiang, Xuemei Wang.  (2016)  Synergistic effect of pyrroloquinoline quinone and graphene nano-interface for facile fabrication of sensitive NADH biosensor.  BIOSENSORS & BIOELECTRONICS,      [PMID:27156055] [10.1016/j.bios.2016.04.092]

8. Yanli Zhou, Hui Dong, Lantao Liu, Yuanqiang Hao, Zhu Chang, Maotian Xu.  (2014)  Fabrication of electrochemical interface based on boronic acid-modified pyrroloquinoline quinine/reduced graphene oxide composites for voltammetric determination of glycated hemoglobin.  BIOSENSORS & BIOELECTRONICS,      [PMID:25286351] [10.1016/j.bios.2014.09.058]

9. Yong Chang, Yajun Wang, Xueqian Fan, Jia Zhou, Yunhe Lv, Ning Xia.  (2024)  Electrochemical immunosensors based on the solubility difference of electroactive probe and the dual signal amplification of nanocarrier plus redox cycling.  BIOELECTROCHEMISTRY,      [PMID:39602974] [10.1016/j.bioelechem.2024.108858]

10. Daoyang Zhu, Qiuya Gu, Xiaobin Yu.  (2025)  Fluorescence-activated cell sorting and random mutagenesis for enhanced pyrroloquinoline quinone accumulation by Hyphomicrobium denitrificans.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2024.109627]

11. Zhao-Jiang Yu, Ting-Ting Yang, Gang Liu, De-Hua Deng, Lin Liu.  (2024)  Gold Nanoparticles-Based Colorimetric Immunoassay of Carcinoembryonic Antigen with Metal–Organic Framework to Load Quinones for Catalytic Oxidation of Cysteine.  SENSORS,  24  (20): (6701).  [PMID:39460180] [10.3390/s24206701]

12. Ning Xia, Fengli Gao, Gang Liu, Yong Chang, Lin Liu.  (2024)  Pyrroloquinoline quinone exhibiting peroxidase-mimicking property for colorimetric assays.  ANALYTICA CHIMICA ACTA,      [PMID:39643317] [10.1016/j.aca.2024.343468]

13. Shan Li, Xiong Xiang, Yinglu Qing, Yanbo Wang, Min Wang, Jiaoyan Ren.  (2024)  The protective effect of antioxidant from the perspective of cell morphology and motility.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2024.103673]

14. Hongxin Zhang, Junxia Liu, Fred Mwabulili, Peng Li, Xiao Li, Yanli Xie, Yuhui Yang, Qian Li, Weibin Ma, Hang Jia, Yuan Tian.  (2025)  The expression, identification, and application of DsDDH: a dehydrogenase from Devosia sp. 63-57 for the biodegradation of deoxynivalenol.  Food Bioscience,      [PMID:] [10.1016/j.fbio.2025.107293]

15. Shengnan Zheng, Chuzhou Wen, Jiaxue Tang, Changkai Sun, Fengtao Wang, Shui Guan.  (2025)  Synthesis and structural characterization of pyrroloquinoline quinone grafted carboxymethyl chitosan copolymer with neuroprotective potential.  International Journal of Polymeric Materials and Polymeric Biomaterials,      [PMID:] [10.1080/00914037.2025.2537951]

16. Fengli Gao, Lin Liu, Cancan He, Yong Chang, Weiqiang Wang.  (2025)  A Metal–Organic Hybrid Composed of Dual Quenching Cofactors as a Nanoquencher for the Fluorescent Determination of Protease Caspase-3.  Biosensors-Basel,  15  (6): (354).  [PMID:40558436] [10.3390/bios15060354]

17. Li Cheng, Jiang Peng, Fan Chenglong, Chen Jinji, Liang Shengsheng, Chen Shaohua, Mi Hua.  (2025)  Characteristics of gut microbiota and metabolites in rats with ketamine-induced cystitis.  Scientific Reports,      [PMID:41392116] [10.1038/s41598-025-31280-y]