Showing Compound Benzocaine (FDB023574)

Record Information

Version

1.0

Creation date

2011-09-21 00:31:49 UTC

Update date

2015-10-09 22:33:11 UTC

Primary ID

FDB023574

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Benzocaine

Description

A 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 Number

94-09-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4-Aminobenzoic acid ethyl ester	ChEBI
Amben ethyl ester	ChEBI
Benzocaina	ChEBI
Benzocainum	ChEBI
Ethyl aminobenzoate	ChEBI
Ethyl p-aminobenzoate	ChEBI
Ethyl p-aminophenylcarboxylate	ChEBI
p-(Ethoxycarbonyl)aniline	ChEBI
p-Carbethoxyaniline	ChEBI
p-Ethoxycarboxylic aniline	ChEBI
Parathesin	Kegg
4-Aminobenzoate ethyl ester	Generator
Ethyl aminobenzoic acid	Generator
Ethyl p-aminobenzoic acid	Generator
Ethyl p-aminophenylcarboxylic acid	Generator
(P-(Ethoxycarbonyl)phenylamine	HMDB
4-(Ethoxycarbonyl)aniline	HMDB
4-(Ethoxycarbonyl)phenylamine	HMDB
4-Aminobenzoate	HMDB
4-Aminobenzoic acid	HMDB
4-Carbethoxyaniline	HMDB
Aethoform	HMDB
Americaine	HMDB, MeSH
Anaesthan-syngala	HMDB
Anaesthesin	HMDB, MeSH
Anaesthin	HMDB
Anestezin	HMDB
Anesthesin	HMDB, MeSH
Anesthesine	HMDB
Anesthone	HMDB
Baby anbesol	HMDB
Benzoak	HMDB
Dermoplast	HMDB
Diet ayds	HMDB
Ethoform	HMDB, MeSH
Ethyl 4-aminobenzoate	HMDB
Ethyl 4-aminobenzoic acid	HMDB
Ethyl P-aminobenzenecarboxylate	HMDB
Ethylester kyseliny P-aminobenzoove	HMDB
Hurricaine	HMDB
Identhesin	HMDB
Keloform	HMDB
Norcain	HMDB
Norcaine	HMDB
Ora-jel	HMDB
Orabase-b	HMDB
Orthesin	HMDB
P-Aminobenzoate	HMDB
P-Aminobenzoic acid	HMDB
P-Aminobenzoic acid ethyl ester	HMDB
Parathesine	HMDB
Slim mint gum	HMDB
Solarcaine	HMDB
Solu H	HMDB
Topcaine	HMDB
Benzocaine acetate	MeSH, HMDB
Formate, benzocaine	MeSH, HMDB
Acetate, benzocaine	MeSH, HMDB
Benzocaine formate	MeSH, HMDB
Hydrobromide, benzocaine	MeSH, HMDB
Methanesulfonate, benzocaine	MeSH, HMDB
Bensokain	MeSH, HMDB
Benzocaine hydrochloride	MeSH, HMDB
Benzocaine hydrobromide	MeSH, HMDB
Benzocaine methanesulfonate	MeSH, HMDB
Hydrochloride, benzocaine	MeSH, HMDB
(p-(Ethoxycarbonyl)phenylamine	hmdb
Baby Anbesol	hmdb
Benzocaine	hmdb
Diet Ayds	hmdb
ethyl 4-aminobenzoate	hmdb
ethyl 4-aminobenzoic acid	hmdb
Ethyl p-aminobenzenecarboxylate	hmdb
Ethyl P-aminophenylcarboxylic acid	Generator
Ethylester kyseliny p-aminobenzoove	hmdb
Orabase-B	hmdb
p-Aminobenzoic acid ethyl ester	hmdb
Slim Mint Gum	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	2.85 g/L	ALOGPS
logP	2.2	ALOGPS
logP	1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	2.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.53 m³·mol⁻¹	ChemAxon
Polarizability	17.46 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H11NO2

IUPAC name

ethyl 4-aminobenzoate

InChI Identifier

InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3

InChI Key

BLFLLBZGZJTVJG-UHFFFAOYSA-N

Isomeric SMILES

CCOC(=O)C1=CC=C(N)C=C1

Average Molecular Weight

165.1891

Monoisotopic Molecular Weight

165.078978601

Classification

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

substituted aniline (CHEBI:116735 )
benzoate ester (CHEBI:116735 )

Ontology

Disposition

Source:

Synthetic:

Personal care product

Route of exposure:

Parenteral:

Dermal

Enteral:

Ingestion

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00xr-6900000000-0594451f3b181ab3c883	2014-09-20	View Spectrum
GC-MS	Benzocaine, 1 TMS, GC-MS Spectrum	splash10-00dl-0980000000-9bd6d020be04ce49bd3e	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-00di-4900000000-9341302295e361a20bfd	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-0109-9400000000-8e31c925b871e0f0299e	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-0109-9400000000-c755b4e5336a2867357e	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-01b9-1900000000-a811093acfd0672fece6	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-49302e8e4fd5158a36da	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-00di-5900000000-dcd2847110af7c87bf18	Spectrum
GC-MS	Benzocaine, non-derivatized, GC-MS Spectrum	splash10-00dl-0980000000-9bd6d020be04ce49bd3e	Spectrum
Predicted GC-MS	Benzocaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-3900000000-8d1e571ebb0276875b64	Spectrum
Predicted GC-MS	Benzocaine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00kr-0900000000-b54aebb77e7a69ada07c	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-5900000000-ce90658bd0fc66df820d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03xu-9100000000-5179b7804d2c59e71aa4	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00di-4900000000-9341302295e361a20bfd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positive	splash10-0109-9400000000-8e31c925b871e0f0299e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6D) , Positive	splash10-0109-9400000000-c755b4e5336a2867357e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-01b9-1900000000-57d39b512bc5bdbb4987	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-60) , Positive	splash10-014i-0900000000-49302e8e4fd5158a36da	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-DX-300) , Positive	splash10-00di-5900000000-dcd2847110af7c87bf18	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-a0f10abbe67842c2c958	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-00du-5900000000-43a89461a4d9cc5d1409	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00dl-9600000000-049e2653cbbf24aaf010	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-002f-9100000000-6fbc7720b326773643af	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00ou-9000000000-d7f7622c3a270c5ffcbb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-5900100000-72ac4bcb64db0d25261e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-0900000000-e061a0f4172b47a8bd22	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00du-5900000000-54757e57c91d3eaa1976	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00dl-9600000000-049e2653cbbf24aaf010	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-002f-9100000000-e16fc2db7a632fc6f4da	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-4479c2a548f4aa1aa697	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00xr-0900000000-45723c7ad554a9d56bd1	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9300000000-fab7bee6cbcfbc918d9c	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-477a27b8617485132384	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-3900000000-df3eaaf30a4e906fb038	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9400000000-e9f4c1de93ac2ce072b4	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum