424048
2,6-Quinolinediol
Synonym(s):
2,6-Dihydroxyquinoline, 6-Hydroxycarbostyril
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About This Item
Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
Molecular Weight:
161.16
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
InChI
1S/C9H7NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h1-5,11H,(H,10,12)
SMILES string
Oc1ccc2nc(O)ccc2c1
InChI key
AQLYZDRHNHZHIS-UHFFFAOYSA-N
mp
>300 °C (lit.)
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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)
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)
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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