Record Information
Version1.0
Creation date2011-09-21 00:31:49 UTC
Update date2015-10-09 22:33:11 UTC
Primary IDFDB023574
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzocaine
DescriptionA surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings.; Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. Benzocaine is an ester, a compound made from the organic acid PABA (para-aminobenzoic acid) and ethanol. The process in which this ester is created is known as Fischer esterification. [HMDB]
CAS Number94-09-7
Structure
Thumb
Synonyms
SynonymSource
4-Aminobenzoic acid ethyl esterChEBI
Amben ethyl esterChEBI
BenzocainaChEBI
BenzocainumChEBI
Ethyl aminobenzoateChEBI
Ethyl p-aminobenzoateChEBI
Ethyl p-aminophenylcarboxylateChEBI
p-(Ethoxycarbonyl)anilineChEBI
p-CarbethoxyanilineChEBI
p-Ethoxycarboxylic anilineChEBI
ParathesinKegg
4-Aminobenzoate ethyl esterGenerator
Ethyl aminobenzoic acidGenerator
Ethyl p-aminobenzoic acidGenerator
Ethyl p-aminophenylcarboxylic acidGenerator
(P-(Ethoxycarbonyl)phenylamineHMDB
4-(Ethoxycarbonyl)anilineHMDB
4-(Ethoxycarbonyl)phenylamineHMDB
4-AminobenzoateHMDB
4-Aminobenzoic acidHMDB
4-CarbethoxyanilineHMDB
AethoformHMDB
AmericaineHMDB, MeSH
Anaesthan-syngalaHMDB
AnaesthesinHMDB, MeSH
AnaesthinHMDB
AnestezinHMDB
AnesthesinHMDB, MeSH
AnesthesineHMDB
AnesthoneHMDB
Baby anbesolHMDB
BenzoakHMDB
DermoplastHMDB
Diet aydsHMDB
EthoformHMDB, MeSH
Ethyl 4-aminobenzoateHMDB
Ethyl 4-aminobenzoic acidHMDB
Ethyl P-aminobenzenecarboxylateHMDB
Ethylester kyseliny P-aminobenzooveHMDB
HurricaineHMDB
IdenthesinHMDB
KeloformHMDB
NorcainHMDB
NorcaineHMDB
Ora-jelHMDB
Orabase-bHMDB
OrthesinHMDB
P-AminobenzoateHMDB
P-Aminobenzoic acidHMDB
P-Aminobenzoic acid ethyl esterHMDB
ParathesineHMDB
Slim mint gumHMDB
SolarcaineHMDB
Solu HHMDB
TopcaineHMDB
Benzocaine acetateMeSH, HMDB
Formate, benzocaineMeSH, HMDB
Acetate, benzocaineMeSH, HMDB
Benzocaine formateMeSH, HMDB
Hydrobromide, benzocaineMeSH, HMDB
Methanesulfonate, benzocaineMeSH, HMDB
BensokainMeSH, HMDB
Benzocaine hydrochlorideMeSH, HMDB
Benzocaine hydrobromideMeSH, HMDB
Benzocaine methanesulfonateMeSH, HMDB
Hydrochloride, benzocaineMeSH, HMDB
(p-(Ethoxycarbonyl)phenylaminehmdb
Baby Anbesolhmdb
Benzocainehmdb
Diet Aydshmdb
ethyl 4-aminobenzoatehmdb
ethyl 4-aminobenzoic acidhmdb
Ethyl p-aminobenzenecarboxylatehmdb
Ethyl P-aminophenylcarboxylic acidGenerator
Ethylester kyseliny p-aminobenzoovehmdb
Orabase-Bhmdb
p-Aminobenzoic acid ethyl esterhmdb
Slim Mint Gumhmdb
Predicted Properties
PropertyValueSource
Water Solubility2.85 g/LALOGPS
logP2.2ALOGPS
logP1.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)2.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.53 m³·mol⁻¹ChemAxon
Polarizability17.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H11NO2
IUPAC nameethyl 4-aminobenzoate
InChI IdentifierInChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
InChI KeyBLFLLBZGZJTVJG-UHFFFAOYSA-N
Isomeric SMILESCCOC(=O)C1=CC=C(N)C=C1
Average Molecular Weight165.1891
Monoisotopic Molecular Weight165.078978601
Classification
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Aminobenzoic acid or derivatives
  • Benzoate ester
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Route of exposure:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00xr-6900000000-0594451f3b181ab3c883Spectrum
GC-MSBenzocaine, 1 TMS, GC-MS Spectrumsplash10-00dl-0980000000-9bd6d020be04ce49bd3eSpectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-00di-4900000000-9341302295e361a20bfdSpectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-0109-9400000000-8e31c925b871e0f0299eSpectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-0109-9400000000-c755b4e5336a2867357eSpectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-01b9-1900000000-a811093acfd0672fece6Spectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-49302e8e4fd5158a36daSpectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-00di-5900000000-dcd2847110af7c87bf18Spectrum
GC-MSBenzocaine, non-derivatized, GC-MS Spectrumsplash10-00dl-0980000000-9bd6d020be04ce49bd3eSpectrum
Predicted GC-MSBenzocaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3900000000-8d1e571ebb0276875b64Spectrum
Predicted GC-MSBenzocaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kr-0900000000-b54aebb77e7a69ada07cSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-5900000000-ce90658bd0fc66df820dSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03xu-9100000000-5179b7804d2c59e71aa4Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-00di-4900000000-9341302295e361a20bfdSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-0109-9400000000-8e31c925b871e0f0299eSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6D) , Positivesplash10-0109-9400000000-c755b4e5336a2867357eSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-01b9-1900000000-57d39b512bc5bdbb4987Spectrum
MS/MSLC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positivesplash10-014i-0900000000-49302e8e4fd5158a36daSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positivesplash10-00di-5900000000-dcd2847110af7c87bf18Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-a0f10abbe67842c2c958Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00du-5900000000-43a89461a4d9cc5d1409Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00dl-9600000000-049e2653cbbf24aaf010Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-002f-9100000000-6fbc7720b326773643afSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00ou-9000000000-d7f7622c3a270c5ffcbbSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-5900100000-72ac4bcb64db0d25261eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-0900000000-e061a0f4172b47a8bd22Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00du-5900000000-54757e57c91d3eaa1976Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-9600000000-049e2653cbbf24aaf010Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-002f-9100000000-e16fc2db7a632fc6f4daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-4479c2a548f4aa1aa697Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xr-0900000000-45723c7ad554a9d56bd1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-fab7bee6cbcfbc918d9cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1900000000-477a27b8617485132384Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-3900000000-df3eaaf30a4e906fb038Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9400000000-e9f4c1de93ac2ce072b4Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID13854242
ChEMBL IDCHEMBL278172
KEGG Compound IDC07527
Pubchem Compound ID2337
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01086
HMDB IDHMDB04992
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBenzocaine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference