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ChemicalBook >> CAS DataBase List >>4-Hydroxyquinazoline

4-Hydroxyquinazoline

CAS No.
491-36-1
Chemical Name:
4-Hydroxyquinazoline
Synonyms
QUINAZOLIN-4(3H)-ONE;QUINAZOLINONE;4-Oxoquinazoline;QUINAZOLIN-4-OL;quinazolin-4(1H)-one;QUINAZOLONE;4-HQN;β-Nitropropionic acid;AKOS 219-06;AURORA 17795
CBNumber:
CB5182082
Molecular Formula:
C8H6N2O
Molecular Weight:
146.15
MDL Number:
MFCD00511302
MOL File:
491-36-1.mol
MSDS File:
SDS
Last updated:2025-01-27 09:38:02

4-Hydroxyquinazoline Properties

Melting point 216-219 °C (lit.)
Boiling point 265.75°C (rough estimate)
Density 1.2312 (rough estimate)
vapor pressure 0.015Pa at 20℃
refractive index 1.4900 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in DMSO (up to 14 mg/ml) or in Water (up to 1 mg/ml).
form Crystalline Powder
pka 2.69±0.20(Predicted)
color Off-white to light beige
Water Solubility Soluble in DMSO (100 mM), ethanol, methanol, and water (10 mM).
Sensitive Hygroscopic
BRN 118473
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month.
InChIKey QMNUDYFKZYBWQX-UHFFFAOYSA-N
LogP 0.94 at 20℃
CAS DataBase Reference 491-36-1(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 84JOT4EY5X
NIST Chemistry Reference 4(1H)-quinazolinone(491-36-1)
UNSPSC Code 12352100
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-22
Safety Statements  26-37/39-36/37/39-22
WGK Germany  3
RTECS  VA2300000
HazardClass  IRRITANT
HS Code  29335995
NFPA 704
0
2 0

4-Hydroxyquinazoline price More Price(36)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich H57807 4-Hydroxyquinazoline 98% 491-36-1 5g $26.22 2024-03-01 Buy
TCI Chemical H0803 4-Hydroxyquinazoline >98.0%(T) 491-36-1 5g $16 2024-03-01 Buy
TCI Chemical H0803 4-Hydroxyquinazoline >98.0%(T) 491-36-1 25g $39 2024-03-01 Buy
Alfa Aesar A17129 4-Hydroxyquinazoline, 98% 491-36-1 10g $36.65 2024-03-01 Buy
Alfa Aesar A17129 4-Hydroxyquinazoline, 98% 491-36-1 50g $107.65 2024-03-01 Buy
Product number Packaging Price Buy
H57807 5g $26.22 Buy
H0803 5g $16 Buy
H0803 25g $39 Buy
A17129 10g $36.65 Buy
A17129 50g $107.65 Buy

4-Hydroxyquinazoline Chemical Properties,Uses,Production

Description

4-HQN (491-36-1) is an inhibitor of poly(ADP-ribose) polymerase (PARP) (IC50?= 9.5 μM).1?Displays mixed inhibition with respect to NAD+. Protective against ischemia-reperfusion induced ROS production, and subsequent mitochondrial and cell damage in rat heart.2?4-HQN is anti-inflammatory in LPS-induced endotoxic mice?in vivo; decreases NF-κB and AP-1 activation.3

Chemical Properties

off-white to light beige crystalline powder

Uses

4-Hydroxyquinazoline is been used to inhibit PARP (poly(ADP-ribose) synthetase) which catalyzes covalent attachment of the ADP-ribose moiety of NAD+ to various proteins. This compound specifically and potently inhibits PARP-1. 4-HQN demonstrates the ability to decrease activation of transcription factor NFκB and AP-1 in lipopolysaccharide-induced shock. Mechanistic studies indicate that 4-HQN activates PI3-kinase/Akt pathway in the liver, spleen, and lung and down-regulates two elements of the MAP kinase system. Additionally, this agent has been observed to decrease ischemia-reperfusion-induced increase of protein oxidation, single-strand DNA breaks, lipid peroxidation, and mitochondrial reactive oxygen species production in the reperfusion period.

Uses

4-Hydroxyquinazoline shows anti-microbial and anti-carcinogenic activity as seen in studies due to the quinazoline moiety.

Definition

ChEBI: 1H-quinazolin-4-one is a member of quinazolines.

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 1669, 1951 DOI: 10.1021/jo50005a003

Flammability and Explosibility

Not classified

Biological Activity

Inhibitor of poly(ADP-ribose) polymerase (PARP) (IC 50 = 9.5 μ M); displays mixed inhibition with respect to NAD + . Protective against ischemia-reperfusion induced ROS production, and subsequent mitochondrial and cell damage in rat heart. Anti-inflammatory in LPS-induced endotoxic mice in vivo ; decreases NF- κ B and AP-1 activation.

References

1) Banasil?et al. (1992),?Specific inhibitors of poly(ADP-ribose) synthetase and mono(ADP-ribosyl)transferase;? J. Biol. Chem.,?267?1569 2) Halmosi?et al. (2001),?Effect of poly(ADP-ribose) polymerase inhibitors on the ischemia-reperfusion-induced oxidative cell damage and mitochondrial metabolism in Langendorff heart perfusion system.? Clin. Mol. Pharmacol.,?59?1497 3) Veres?et al. (2004),?Regulation of kinase cascades and transcription factors by a poly(ADP-ribose) polymerase-1 inhibitor, 4-hydroxyquinazoline, in lipopolysaccharide-induced inflammation in mice;? J. Pharmacol. Exp. Ther.,?310?247

118-48-9
122-51-0
491-36-1
Synthesis of 4-Hydroxyquinazoline from Isatoic Anhydride and Triethyl orthoformate
Global( 365)Suppliers
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Henan Fengda Chemical Co., Ltd 		+86-371-86557731 +86-13613820652 info@fdachem.com China 20260 58
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View Lastest Price from 4-Hydroxyquinazoline manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
4(3H)-Quinazolinone pictures 2024-11-17 4(3H)-Quinazolinone
491-36-1
 US $48.00 / mg 99.23% 10g TargetMol Chemicals Inc.
4-Hydroxyquinazoline pictures 2024-04-09 4-Hydroxyquinazoline
491-36-1
 US $8.00-0.80 / KG 1KG 99% g-kg-tons, free sample is available Henan Fengda Chemical Co., Ltd
4-Hydroxyquinazoline pictures 2022-03-04 4-Hydroxyquinazoline
491-36-1
 US $1.10 / g 1g 99.00% 100 Tons Dideu Industries Group Limited
4(3H)-Quinazolone 4-Quinazolinone Quinazolone, 4- quinazolidin-4-one 1H-quinazolin-4-one TIMTEC-BB SBB005858 AURORA 17795 4-HYDROXYQUINAZOLINE 4-QUINAZOLINO 4-QUINAZOLINOL 4-QUINAZOLONE 4-(1H)-QUINAZOLINONE 4(3H)-QUINAZOLINONE AKOS 219-06 AKOS BBS-00002691 3,4-Dihydroquinazolin-4-One 4-Hydroxyquizoline 3H-QUINAZOLIN-4-ONE 4(1H)-Quinazolinone (6CI,7CI,8CI,9CI) 4-Hydroxyquinazoline,98% 4-Hydroxyquinazoline for synthesis 4-Hydroxyquinazoline, 98% 5GR quinazoline-4(3H)-one 4-HydroxyquinazoL Quinazolin-4-ol, 4-Quinazolinol JACS-491-36-1 4-Hydroxyquinazoline> 4-Hydroxyquinazoline ISO 9001：2015 REACH Chinazolin-4(1H)-on β-Nitropropionic acid QUINAZOLINONE quinazolin-4(1H)-one 4-HQN QUINAZOLONE QUINAZOLIN-4-OL QUINAZOLIN-4(3H)-ONE 4-Oxoquinazoline Phenol,2,2'-[1,7-ethanediylbis(iminomethylene)]bis- 2-Naphthalenecarboxylicacid,10-amino-,methylester 491-36-1 ALCOHOL Quinazolines Heterocyclic Building Blocks Building Blocks Bioactive Small Molecules Building Blocks Cell Biology Chemical Synthesis H Heterocyclic Building Blocks Quinazolines Caspases/Apoptosis quinazolinone Quinolines, Quinazolines and derivatives Alcohols and Derivatives Heterocycles PYRIMIDINE