4-quinolone

Names

[ CAS No. ]:
611-36-9

[ Name ]:
4-quinolone

[Synonym ]:
4-Quinolinol
Chinolin-4-ol
p-hydroxyquinoline
4-quinolone
4(1H)-QUINOLINONE
Chinolin-4(1H)-on
Quinolin-4(1H)-one
quinolin-4-one
1,4-Dihydroquinoline-4-one
HYDROXYQUINOLINE,4
4-hydroxyquinoline acid
KYNURINE
4-Hydroxyquinoline
4-oxo-1,4-dihydroquinoline
4-hydroxy-quinolin
EINECS 210-268-2
quinolin-4-ol
quinoline-4-ol
MFCD00006777

Biological Activity

[Description]:

4-Quinolone (Kynurine) is a quinoline derivative. Kynurine pathway modulates tryptophan metabolism and involves in neuroprotective effect. Kynurine promotes tumor cell survival and motility by suppressing antitumor immune[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Neurological Disease

[In Vitro]

4-Quinolone (Kynurine) promotes tumor cell survival and motility by suppressing antitumor immune responses through AhR in an autocrine/paracrine fashion. This system is particularly active in human brain tumors where the activation of AhR enhances the expression of TDO producing more kynurine and kynurinic acid. In the healthy human brain, very low levels of TDO exist, whereas, in human brain tumors, the TDO protein levels increase with malignancy[3].

[References]

[1]. Pellicciari R, et al. Modulation of the kynurine pathway of tryptophan metabolism in search for neuroprotective agents. Focus on kynurenine-3-hydroxylase. Adv Exp Med Biol. 2003;527:621-8.

[2]. Marija Pinne, et al. Cytochrome P450 Gene Regulation: Reporter Assays to Assess Aryl Hydrocarbon Receptor (HLHE76, AhR) Activation and Antagonism. Cytochrome P450. pp 157-174.

[3]. Opitz CA, et al. An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor. Nature. 2011 Oct 5;478(7368):197-203.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
313.0±15.0 °C at 760 mmHg

[ Melting Point ]:
200-202 °C(lit.)

[ Molecular Formula ]:
C₉H₇NO

[ Molecular Weight ]:
145.158

[ Flash Point ]:
143.1±20.4 °C

[ Exact Mass ]:
145.052765

[ PSA ]:
33.12000

[ LogP ]:
2.45

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.691

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC4070000

CHEMICAL NAME :: 4-Quinolinol

CAS REGISTRY NUMBER :: 611-36-9

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H7-N-O

MOLECULAR WEIGHT :: 145.17

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
VC4070000

[ HS Code ]:
2933499090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Synergistic antidepressant-like effect of ferulic acid in combination with piperine: involvement of monoaminergic system.

Metab. Brain Dis. 30 , 1505-14, (2015)

The lifetime prevalence rate for major depressive disorder (MDD) is approximately 17 % for most developed countries around the world. Dietary polyphenols are currently used as an adjuvant therapy to a...

Evolution from a natural flavones nucleus to obtain 2-(4-Propoxyphenyl)quinoline derivatives as potent inhibitors of the S. aureus NorA efflux pump.

J. Med. Chem. 54 , 5722-36, (2011)

Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resi...

Antioxidant properties of 4-quinolones and structurally related flavones.

Bioorg. Med. Chem. 20 , 809-18, (2012)

Neurodegenerative disorders are frequently associated with increased oxidative damage to the brain as a result of free radicals produced by cellular respiration. The onset and progression of neurodege...