8-Hydroxyquinoline
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Basic Info
| Common Name | 8-Hydroxyquinoline(F06244) |
| 2D Structure | |
| FRCD ID | F06244 |
| CAS Number | 148-24-3 |
| PubChem CID | 1923 |
| Formula | C9H7NO |
| IUPAC Name | quinolin-8-ol |
| InChI Key | MCJGNVYPOGVAJF-UHFFFAOYSA-N |
| InChI | InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H |
| Canonical SMILES | C1=CC2=C(C(=C1)O)N=CC=C2 |
| Isomeric SMILES | C1=CC2=C(C(=C1)O)N=CC=C2 |
| Synonyms |
Quinophenol
8-HYDROXYQUINOLINE
quinolin-8-ol
8-quinolinol
148-24-3
Oxyquinoline
Oxine
8-Quinol
8-Oxyquinoline
Phenopyridine
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Quinolines and derivatives |
| Subclass | 8-hydroxyquinolines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | 8-hydroxyquinolines |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | 8-hydroxyquinoline - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Pyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as 8-hydroxyquinolines. These are compounds containing a quinoline moiety, which carries a hydroxy group at the 8-position. Quinoline consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 145.161 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Complexity | 138 |
| Monoisotopic Mass | 145.053 |
| Exact Mass | 145.053 |
| XLogP | 2 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9747 |
| Human Intestinal Absorption | HIA+ | 0.9969 |
| Caco-2 Permeability | Caco2+ | 0.7287 |
| P-glycoprotein Substrate | Non-substrate | 0.7132 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9716 |
| Non-inhibitor | 0.9513 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8064 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5166 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7663 |
| CYP450 2D6 Substrate | Non-substrate | 0.7506 |
| CYP450 3A4 Substrate | Non-substrate | 0.6855 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8585 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9236 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8461 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7385 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9401 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.8180 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8878 |
| Non-inhibitor | 0.8914 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.9614 |
| Fish Toxicity | Low FHMT | 0.5714 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6933 |
| Honey Bee Toxicity | High HBT | 0.6529 |
| Biodegradation | Not ready biodegradable | 0.7809 |
| Acute Oral Toxicity | III | 0.7863 |
| Carcinogenicity (Three-class) | Non-required | 0.7354 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.4056 | LogS |
| Caco-2 Permeability | 1.4460 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0520 | LD50, mol/kg |
| Fish Toxicity | 2.3570 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.7562 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| FRUITS, FRESH or FROZEN; TREE NUTS | 0100000 | European Union | 0.01* | 20/10/2013 | |
| Citrus fruits | 0110000 | European Union | 0.01* | 20/10/2013 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.01* | 20/10/2013 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 20/10/2013 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 20/10/2013 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.01* | 20/10/2013 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.01* | 20/10/2013 | |
| Others (2) | 0110990 | European Union | 0.01* | 20/10/2013 | |
| Tree nuts | 0120000 | European Union | 0.01* | 20/10/2013 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.01* | 20/10/2013 | |
| Brazil nuts | 0120020 | European Union | 0.01* | 20/10/2013 | |
| Cashew nuts | 0120030 | European Union | 0.01* | 20/10/2013 | |
| Chestnuts | 0120040 | European Union | 0.01* | 20/10/2013 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.01* | 20/10/2013 | |
| Macadamias | 0120070 | European Union | 0.01* | 20/10/2013 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.01* | 20/10/2013 | |
| Pistachios | 0120100 | European Union | 0.01* | 20/10/2013 | |
| Walnuts | 0120110 | European Union | 0.01* | 20/10/2013 | |
| Others (2) | 0120990 | European Union | 0.01* | 20/10/2013 | |
| Pome fruits | 0130000 | European Union | 0.01* | 20/10/2013 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Biopolymer strategy for the treatment of Wilson's disease. | J Control Release | 2018 Mar 10 | 29407674 |
| Iron species determination by task-specific ionic liquid-based in situ solventformation dispersive liquid-liquid microextraction combined with flame atomicabsorption spectrometry. | J Sci Food Agric | 2017 Oct | 28369892 |
| Solid Phase Extraction Preconcentration Method for Simultaneous Determination of Cadmium, Lead, and Nickel in Poultry Supplements. | J AOAC Int | 2017 Jul 1 | 28251882 |
| Evaluation of antibacterial potential and toxicity of plant volatile compoundsusing new broth microdilution volatilization method and modified MTT assay. | Fitoterapia | 2017 Apr | 28223069 |
| A new aldehyde oxidase catalyzing the conversion of glycolaldehyde to glycolatefrom Burkholderia sp. AIU 129. | J Biosci Bioeng | 2015 Apr | 25283808 |
| Biosorption of Al(+3) and Cd(+2) by an exopolysaccharide from Lactobacillusrhamnosus. | J Food Sci | 2014 Nov | 25308465 |
| Preconcentration of some metal ions with lanthanum-8-hydroxyquinolineco-precipitation system. | Food Chem | 2014 Mar 15 | 24206710 |
| Graphite furnace atomic absorption spectrometric detection of vanadium in waterand food samples after solid phase extraction on multiwalled carbon nanotubes. | Talanta | 2013 Nov 15 | 24148394 |
| Determination of trace bismuth in human serum by cloud point extraction coupledflow injection inductively coupled plasma optical emission spectrometry. | J Hazard Mater | 2011 Sep 15 | 21824726 |
| A novel microextraction technique based on 1-hexylpyridinium hexafluorophosphate ionic liquid for the preconcentration of zinc in water and milk samples. | Anal Chim Acta | 2009 Sep 7 | 19699396 |
| Curcumin reduces the toxic effects of iron loading in rat liver epithelial cells. | Liver Int | 2009 Jan | 18492020 |
| Speciation of aluminum in drink samples by 8-hydroxyquinoline loadedsilylanization silica gel microcolumn separation with off-line ICP-MS detection. | J Agric Food Chem | 2004 Nov 17 | 15537284 |
| Complexation of several fungicides with beta-cyclodextrin: determination of theassociation constants and isolation of the solid complexes. | J Agric Food Chem | 2003 Aug 13 | 12903966 |
| Improved immobilization of 8-hydroxyquinoline on polyacrylonitrile fiber andapplication of the material to the determination of trace metals in seawater byinductively coupled plasma mass spectrometry. | Anal Bioanal Chem | 2002 Nov | 12434254 |
| Direct and selective flow-injection method for the simultaneousspectrophotometric determination of calcium and magnesium in red and white wines using online dilution based on "Zone Sampling". | J Agric Food Chem | 2001 Nov | 11714295 |
| Use of 8-hydroxyquinoline-beta-D-glucuronide for presumptive identification of Shiga toxin-producing Escherichia coli O157. | Lett Appl Microbiol | 2000 May | 10792673 |
| [In vivo toxicity, lipid peroxide lowering, and glutathione, ascorbic acid and copper elevation induced in mouse liver by low dose of oxine-copper, a fungicide]. | Yakugaku Zasshi | 2000 Mar | 10723274 |
| Xanthophyll biosynthesis: molecular and functional characterization of carotenoidhydroxylases from pepper fruits (Capsicum annuum L.). | Biochim Biophys Acta | 1998 Apr 22 | 9555077 |
| Aluminium and fluoride in hospital daily diets and in teas. | Z Lebensm Unters Forsch | 1995 Oct | 8525696 |
| Quinoline anti-malarial drugs inhibit spontaneous formation of beta-haematin (malaria pigment). | FEBS Lett | 1994 Sep 19 | 7925942 |