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424048

Sigma-Aldrich

2,6-Quinolinediol

Synonym(s):

2,6-Dihydroxyquinoline, 6-Hydroxycarbostyril

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About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
19315-93-6
Molecular Weight:
161.16
MDL number:
MFCD00239446
UNSPSC Code:
12352100
PubChem Substance ID:
24866548
NACRES:
NA.22

mp

>300 °C (lit.)

SMILES string

Oc1ccc2nc(O)ccc2c1

InChI

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

InChI key

AQLYZDRHNHZHIS-UHFFFAOYSA-N

General description

2,6-Quinolinediol is a substituted quinoline compound. It has been prepared starting from 6-methoxyquinoline. It has been reported to be one of the UV-absorbing compounds (UAC) found in cow milk.

Application

2,6-Quinolinediol may be used as a test compound to investigate the carcinogenicity of the naturally occurring quinoline metabolite of tryptophan. The study was conducted by suspending tryptophan metabolites in cholesterol pellets, followed by the surgical implantation of the pellets into the mice bladder. It may be used as a reactant in the synthesis of 2-chloro-6-quinolinol by reacting with POCl3 (phosphorus oxychloride).
Reactant involved in synthesis of:
  • (Benzyloxy)methylquinolinone derivatives for use as PDE3 inhibitors
  • Substances related to cilostazol
  • 2,6-Quinolinyl derivatives for use as VLA-4 / VCAM-1 antagonists

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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In vivo elution of tryptophan metabolites and other aromatic nitrogen compounds from cholesterol pellets implanted into mouse bladders.
Bryan GT, et al.
Cancer Research, 24(4), 586-595 (1964)
2, 6-Quinolinyl derivatives as potent VLA-4 antagonists.
Lassoie MA, et al.
Bioorganic & Medicinal Chemistry Letters, 17(1), 142-146 (2007)
Mouse bladder carcinogenicity of certain tryptophan metabolites and other aromatic nitrogen compounds suspended in cholesterol.
Bryan GT, et al.
Cancer Research, 24(4), 596-602 (1964)
Pascal Rouge et al.
Food chemistry, 141(3), 1888-1894 (2013-07-23)
The aim of this work was to characterise new UV-absorbing compounds (UAC) in cow milk in order to gain an overview of the molecular diversity of the minor bioactive constituents, that could be used to trace animal feed or that

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