ContaminantDB: Quinoline

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:59:16 UTC

Update Date

2026-05-14 20:06:16 UTC

Accession Number

CHEM000563

Identification

Common Name

Quinoline

Class

Small Molecule

Description

Quinoline is found in alcoholic beverages. Quinoline is an alkaloid from various plant species including Mentha species. Also present in cocoa, black tea and scotch whiskey. Quinoline is a flavouring ingredient Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name Assert. Quinoline has been shown to exhibit catabolic, anti-microbial, anti-tumor, anti-fungal and anti-cancer functions (4, 5, 6, 7, 8).

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Pesticide
Plant Toxin
Pollutant
Polycyclic Aromatic Hydrocarbon

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Benzo[b]pyridine	ChEBI
Chinolin	ChEBI
Quinoline hydrochloride	MeSH
1-Azanaphthalene	HMDB
1-Benzazine	HMDB
1-Benzine	HMDB
2,3-Benzopyridine	HMDB
benzo(b)Pyridine	HMDB
Chinoleine	HMDB
Chinoline	HMDB
FEMA 3470	HMDB
Leucol	HMDB
Leukol	HMDB
Quinolin	HMDB
Quinoline (8ci,9ci)	HMDB

Chemical Formula

C₉H₇N

Average Molecular Mass

129.159 g/mol

Monoisotopic Mass

129.058 g/mol

CAS Registry Number

91-22-5

IUPAC Name

quinoline

Traditional Name

cinch

SMILES

C1=CC=C2N=CC=CC2=C1

InChI Identifier

InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H

InChI Key

SMWDFEZZVXVKRB-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as quinolines and derivatives. Quinolines and derivatives are compounds containing a quinoline moiety, which consists of a benzene ring fused to a pyrimidine ring to form benzo[b]azabenzene.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Not Available

Direct Parent

Quinolines and derivatives

Alternative Parents

Substituents

Quinoline
Benzenoid
Pyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:17362 )
mancude organic heterobicyclic parent (CHEBI:17362 )
azaarene (CHEBI:17362 )
ortho-fused heteroarene (CHEBI:17362 )
a small molecule (QUINOLINE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless solid.

Experimental Properties

Property	Value
Melting Point	-15.6°C
Boiling Point	238°C (460.4°F)
Solubility	6.11 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	3.37 g/L	ALOGPS
logP	2.19	ALOGPS
logP	2.13	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Basic)	4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.89 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	39.98 m³·mol⁻¹	ChemAxon
Polarizability	13.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-6650a64dcfaff97a384f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9700000000-162da149cecb7471177e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-589a1fb16b83c4fe8115	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-f63ba1bba58ccc63c20a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-06d1e2a8216798421e17	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-5f026eea98547624a47f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-5f026eea98547624a47f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-6650a64dcfaff97a384f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fb9-9700000000-162da149cecb7471177e	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-589a1fb16b83c4fe8115	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-f63ba1bba58ccc63c20a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-06d1e2a8216798421e17	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-5f026eea98547624a47f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-5f026eea98547624a47f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-0900000000-5bfb659404cb36aa304f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-f80d7ca98d120817a55c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-027cf5e71116c5fcb4b6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-b503a364d204d8e6ac8c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-8900000000-49aa8f9641f21e97fc43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9100000000-25969cc68eb743f7f3df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-7ca73e074935b2add2f4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-a45f6683fe6d4b0b16aa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-0900000000-7026ebf0519b2fba0024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-001i-1900000000-09e171e9467e40b551d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0fai-4900000000-7b17c392210401ee485d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-ITFT , positive	splash10-0fba-9700000000-581ee9456c67170a0520	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - APCI-ITFT , positive	splash10-001i-0900000000-f501f97d31380e58bdab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-6596d88125ed21410c6d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0900000000-6c1f93bf41d02c99ce73	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-3900000000-7293ce5372993b70ea55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-f7d71396a8498e54005a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-f7d71396a8498e54005a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900000000-678317c07cf462bbdfa9	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-4900000000-f18da8f2e791614f0c9a	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (9) ; inhalation (9)

Mechanism of Toxicity

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (9, 10, 2, 3)

Metabolism

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (9)

Toxicity Values

LD50: 331 mg/kg (Oral, Rat) (12) LD50: 540 mg/kg (Dermal, Rabbit) (12)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC. IARC has evaluated related PAHs (11).

Uses/Sources

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (9)

Minimum Risk Level

Not Available

Health Effects

PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (9)

Symptoms

Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (1)

Treatment

There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (9)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0033731

FooDB ID