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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:01:10 UTC
Update Date2021-10-13 23:08:09 UTC
HMDB IDHMDB0039531
Secondary Accession Numbers
  • HMDB39531
Metabolite Identification
Common NameEthoxyquin
DescriptionEthoxyquin is an antioxidant used in animal feeds and for the preservation of colour in the production of chili powder, paprika and ground chilli. Ethoxyquin is formerly used as an agricultural pesticide/herbicide, now superseded. Also used as a post-harvest dip for apples and pears to prevent scald.
Structure
Data?1563863392
Synonyms
ValueSource
1,2-Dihydro-2,2,4-trimethyl-6-ethoxyquinolineChEBI
1,2-Dihydro-6-ethoxy-2,2,4-trimethylquinolineChEBI
2,2,4-Trimethyl-6-ethoxy-1,2-dihydroquinolineChEBI
6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinolineChEBI
e 324ChEBI
e324ChEBI
EthoxyquineChEBI
Ethyl 2,2,4-trimethyl-1,2-dihydro-6-quinolinyl etherChEBI
(-)-LobelineHMDB
2,2, 4-Trimethyl-6-ethoxy-1,2-dihydroquinolineHMDB
6-(Ethyloxy)-2,2,4-trimethyl-1,2-dihydroquinolineHMDB
6-Ethoxy-1, 2-dihydro-2,2,4-trimethylquinolineHMDB
6-Ethoxy-1,2-dihydro-2,2,4-trimethyl-quinolineHMDB
6-Ethoxy-1,2-dihydro-2,2,4-trimethylquinoline, 9ci, 8ciHMDB
6-Ethoxy-2,2,4-trimethyl-1, 2-dihydroquinolineHMDB
6-Ethoxy-2,2,4-trimethyl-1,2-dihydroquinolineHMDB
6-ETMDQHMDB
Alterungsschutzmittel ecHMDB
Antage awHMDB
Antioxidant ecHMDB
AntoxHMDB
Aries antoxHMDB
Dawe'S nutrigardHMDB
EMQHMDB
EQHMDB
EthoxychinHMDB
LobelineHMDB
NiflexHMDB
Niflex DHMDB
Nix-scaldHMDB
Nocrac awHMDB
Nocrack awHMDB
Permanax 103HMDB
PolyflexHMDB
Quinol edHMDB
SantoflexHMDB
Santoflex aHMDB
Santoflex awHMDB
SantoquinHMDB
SantoquineHMDB
SantoquineqHMDB
Stop-scaldHMDB
Chemical FormulaC14H19NO
Average Molecular Weight217.3068
Monoisotopic Molecular Weight217.146664235
IUPAC Name6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline
Traditional Nameethoxyquin
CAS Registry Number91-53-2
SMILES
CCOC1=CC2=C(NC(C)(C)C=C2C)C=C1
InChI Identifier
InChI=1S/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3
InChI KeyDECIPOUIJURFOJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentHydroquinolones
Alternative Parents
Substituents
  • Dihydroquinolone
  • Dihydroquinoline
  • Alkyl aryl ether
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Azacycle
  • Secondary amine
  • Ether
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point332.00 to 333.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility17.46 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.105 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP10(4.01) g/LALOGPS
logP10(3) g/LChemAxon
logS10(-2.9) g/LALOGPS
pKa (Strongest Basic)5.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity69.68 m³·mol⁻¹ChemAxon
Polarizability25.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.62431661259
DarkChem[M-H]-151.88631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthoxyquinCCOC1=CC2=C(NC(C)(C)C=C2C)C=C12384.8Standard polar33892256
EthoxyquinCCOC1=CC2=C(NC(C)(C)C=C2C)C=C11737.9Standard non polar33892256
EthoxyquinCCOC1=CC2=C(NC(C)(C)C=C2C)C=C11776.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Ethoxyquin,1TMS,isomer #1CCOC1=CC=C2C(=C1)C(C)=CC(C)(C)N2[Si](C)(C)C1853.1Semi standard non polar33892256
Ethoxyquin,1TMS,isomer #1CCOC1=CC=C2C(=C1)C(C)=CC(C)(C)N2[Si](C)(C)C1919.0Standard non polar33892256
Ethoxyquin,1TBDMS,isomer #1CCOC1=CC=C2C(=C1)C(C)=CC(C)(C)N2[Si](C)(C)C(C)(C)C2116.4Semi standard non polar33892256
Ethoxyquin,1TBDMS,isomer #1CCOC1=CC=C2C(=C1)C(C)=CC(C)(C)N2[Si](C)(C)C(C)(C)C2172.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethoxyquin GC-MS (1 TMS)splash10-00dj-2690000000-2b783a3c0e06c9476b862014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethoxyquin GC-MS (Non-derivatized)splash10-00dj-2690000000-2b783a3c0e06c9476b862017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethoxyquin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fki-0920000000-e7b66012b60323079c3c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethoxyquin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uk9-1980000000-25958a756414a66315472014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-014i-0090000000-a10faf6f2ad9a301d3282017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-014i-0090000000-4e661aa96345ca11a4dc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-014i-0970000000-95e3dd12809eada73bd02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-0hmw-0910000000-30509ee0b909df1db28b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-01wb-0900000000-ac750e6f3eb663d9dda42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-01wb-0900000000-6ac6089762818c098d382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-02aj-2900000000-8cf867953c6d56b1df7b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-0159-4900000000-29f53200e56ee7740ec22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin LC-ESI-QFT , positive-QTOFsplash10-0159-8900000000-c30df52c0104a240a1652017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 45V, Positive-QTOFsplash10-014i-0960000000-ea4a09ea32cff102e76c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 60V, Positive-QTOFsplash10-01vt-0910000000-8cc1fa05bcdbd09e32e92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 30V, Positive-QTOFsplash10-014i-0190000000-fa3625e950af550b6d232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 15V, Positive-QTOFsplash10-014i-0090000000-3601351bc5c6b77367892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 30V, Positive-QTOFsplash10-014i-0090000000-494356038cb566f97b412021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 75V, Positive-QTOFsplash10-01wb-0900000000-7bd39873f18f852a57442021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 90V, Positive-QTOFsplash10-01wb-0900000000-04e5d011d9ab9b1526052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 120V, Positive-QTOFsplash10-02aj-2900000000-2060e3cd29f3dcc873842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 15V, Positive-QTOFsplash10-014i-0090000000-76c8d5edb3bd28e19bec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Ethoxyquin 45V, Positive-QTOFsplash10-014i-0980000000-bb83ab7a0c4f542d856d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxyquin 10V, Positive-QTOFsplash10-014i-0190000000-8be63631af40c6c4279a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxyquin 20V, Positive-QTOFsplash10-014i-1970000000-42c681d6c7c9f7b238fe2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxyquin 40V, Positive-QTOFsplash10-05fr-1900000000-dec276bdd56140e41f8b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxyquin 10V, Negative-QTOFsplash10-014i-0190000000-421634377cab228d85032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxyquin 20V, Negative-QTOFsplash10-014r-0980000000-26cd4b9aa32fdb7654882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethoxyquin 40V, Negative-QTOFsplash10-00di-0900000000-fade67d3785d3b8dac3b2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019147
KNApSAcK IDC00052159
Chemspider ID3177
KEGG Compound IDC07475
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthoxyquin
METLIN IDNot Available
PubChem Compound3293
PDB IDNot Available
ChEBI ID77323
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1353101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .