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Showing Compound Quinoline (FDB011854)

Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2019-11-26 03:05:34 UTC
Primary IDFDB011854
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameQuinoline
DescriptionAlkaloid from various plant subspecies including Mentha subspeciesand is also present in cocoa, black tea and scotch whiskey. 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 is found in many foods, some of which are tea, alcoholic beverages, cocoa and cocoa products, and herbs and spices.
CAS Number91-22-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Benzo[b]pyridineChEBI
ChinolinChEBI
Quinoline hydrochlorideMeSH
1-AzanaphthaleneHMDB
1-BenzazineHMDB
1-BenzineHMDB
2,3-BenzopyridineHMDB
benzo(b)PyridineHMDB
ChinoleineHMDB
ChinolineHMDB
FEMA 3470HMDB
LeucolHMDB
LeukolHMDB
QuinolinHMDB
Quinoline (8ci,9ci)HMDB
Benzo(b)pyridinebiospider
Quinoline (8CI,9CI)biospider
Quinoline [UN2656] [Poison]biospider
Predicted Properties
PropertyValueSource
Water Solubility3.37 g/LALOGPS
logP2.19ALOGPS
logP2.13ChemAxon
logS-1.6ALOGPS
pKa (Strongest Basic)4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.89 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.98 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H7N
IUPAC namequinoline
InChI IdentifierInChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H
InChI KeySMWDFEZZVXVKRB-UHFFFAOYSA-N
Isomeric SMILESC1=CC=C2N=CC=CC2=C1
Average Molecular Weight129.1586
Monoisotopic Molecular Weight129.057849229
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNot Available
Direct ParentQuinolines and derivatives
Alternative Parents
Substituents
  • Quinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 83.69%; H 5.46%; N 10.84%DFC
Melting PointFp -15.6°DFC
Boiling PointBp17 114°DFC
Experimental Water Solubility6.11 mg/mL at 25 oCSMITH,JH et al. (1978)
Experimental logP2.03HANSCH,C ET AL. (1995)
Experimental pKapKa 4.9 (20°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.09DFC
Refractive Indexn20D 1.6268DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-4900000000-f18da8f2e791614f0c9a2014-09-20View Spectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-6650a64dcfaff97a384fSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-0fb9-9700000000-162da149cecb7471177eSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-589a1fb16b83c4fe8115Spectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-5900000000-f63ba1bba58ccc63c20aSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-06d1e2a8216798421e17Spectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-6650a64dcfaff97a384fSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-0fb9-9700000000-162da149cecb7471177eSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-0900000000-589a1fb16b83c4fe8115Spectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-5900000000-f63ba1bba58ccc63c20aSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-4900000000-06d1e2a8216798421e17Spectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
GC-MSQuinoline, non-derivatized, GC-MS Spectrumsplash10-004i-2900000000-5f026eea98547624a47fSpectrum
Predicted GC-MSQuinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fb9-0900000000-5bfb659404cb36aa304fSpectrum
Predicted GC-MSQuinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSQuinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-f80d7ca98d120817a55c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-027cf5e71116c5fcb4b62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-b503a364d204d8e6ac8c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-8900000000-49aa8f9641f21e97fc432017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9100000000-25969cc68eb743f7f3df2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7ca73e074935b2add2f42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-a45f6683fe6d4b0b16aa2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-0900000000-7026ebf0519b2fba00242017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-001i-1900000000-09e171e9467e40b551d22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fai-4900000000-7b17c392210401ee485d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0fba-9700000000-581ee9456c67170a05202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-001i-0900000000-f501f97d31380e58bdab2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-6596d88125ed21410c6d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6c1f93bf41d02c99ce732016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-3900000000-7293ce5372993b70ea552016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-f7d71396a8498e54005a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-f7d71396a8498e54005a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-1900000000-678317c07cf462bbdfa92016-08-03View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
ChemSpider ID6780
ChEMBL IDCHEMBL14474
KEGG Compound IDC06413
Pubchem Compound ID7047
Pubchem Substance IDNot Available
ChEBI ID17362
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33731
CRC / DFC (Dictionary of Food Compounds) IDGZZ73-X:GZZ73-X
EAFUS ID3281
Dr. Duke IDQUINOLINE
BIGG IDNot Available
KNApSAcK IDC00026478
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1009431
SuperScent IDNot Available
Wikipedia IDQuinoline
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
preservative65255 Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
medical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rubber
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
earthy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).