37640

Sigma-Aldrich

2,8-Quinolinediol

≥99.0% (HPLC)

Synonym(s):
2,8-Dihydroxyquinoline
Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
Molecular Weight:
161.16
Beilstein/REAXYS Number:
472906
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

≥99.0% (HPLC)

mp

~290 °C (dec.)

SMILES string

Oc1ccc2cccc(O)c2n1

InChI

1S/C9H7NO2/c11-7-3-1-2-6-4-5-8(12)10-9(6)7/h1-5,11H,(H,10,12)

InChI key

ZXZKYYHTWHJHFT-UHFFFAOYSA-N

General description

2,8-Quinolinediol is a quinolone derivative. It has been reported as metabolite of 8-hydroxyquinoline-N-oxide in rabbits. Synthesis of 2,8-quinolinediol has been reported. It is reported as one of the six possible forms of 8-hydroxycarbostyril. It has been detected as new UV-absorbing compound (UAC) in cow milk and its structure was elucidated using HRMS and by 1H, 13C and 1H ×13C NMR.It is also known as 8-hydroxycarbostyril or 8-hydroxyquinolin-2(1H)-one.
8-hydroxyquinolin-2(1H)-one has been reported as the tautomeric form of 2,8-quinolinediol. 2,8-Quinolinediol (2,8-Dihydroxyquinoline) has been identified as one of the metabolite of quinolone formed in the culture medium of gram-negative bacteria, Pseudomonas stutzeri.

Application

2,8-Quinolinediol is suitable for use as standard in a study to identify the urinary metabolites for the toxicity related processes and pathogenesis induced by doxorubicin (DOX) to rats by online and off-line LC-MS techniques. It may be used as starting reagent for the preparation of two powerful β2-adrenergic receptor agonists, used for the treatment of asthma:
  • Procaterol
  • Indacaterol

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26-36

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Two polymorphs of 8-hydroxycarbostyril: X-ray crystallography, solid-state NMR and DFT calculations.
Nieto CI, et al.
Journal of Molecular Structure, 1008, 88-94 (2012)
Jiangshan Wang et al.
Metabolomics : Official journal of the Metabolomic Society, 5(4), 407-418 (2010-01-05)
A metabolomics-based systems toxicology approach was used to profile the urinary metabolites for the toxicity related processes and pathogenesis induced by doxorubicin (DOX) to rats. Endogenous metabolite profiles were obtained with ultra performance liquid chromatography-mass spectrometry (UPLC-MS) for rats receiving...
Muhammad Bilal et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 183, 417-424 (2017-05-06)
A green tunable dispersive liquid-liquid micro extraction (TDLLME) technique was established for the simultaneous enrichment of lead (Pb) and cadmium (Cd) from different lakes water before analysis by flame atomic absorption spectrometry (FAAS). A solvent known as tunable polarity solvent...
O P Shukla
Microbios, 59(238), 47-63 (1989-01-01)
A Gram-negative, oxidase positive, polar flagellated rod, characterised as Pseudomonas stutzeri, has been isolated from sewage by enrichment culture on quinoline. The organism utilizes quinoline as the sole source of carbon, nitrogen and energy, and liberates UV absorbing and phenolic...
O P Shukla
Applied and environmental microbiology, 51(6), 1332-1342 (1986-06-01)
A Pseudomonas sp. isolated from sewage by enrichment culture on quinoline metabolized this substrate by a novel pathway involving 8-hydroxycoumarin. During early growth of the organism on quinoline, 2-hydroxyquinoline accumulated as the intermediate; 8-hydroxycoumarin accumulated as the major metabolite on...

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