Record Information
Version1.0
Creation date2010-04-08 22:04:48 UTC
Update date2020-09-17 15:40:49 UTC
Primary IDFDB001037
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Aminobenzoic acid
Descriptionp-Aminobenzoic acid, also known as PABA or p-aminobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. p-Aminobenzoic acid is a moderately basic compound (based on its pKa). p-Aminobenzoic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, p-Aminobenzoic acid is found, on average, in the highest concentration within pineapples. p-Aminobenzoic acid has also been detected, but not quantified in, milk (cow) and rices. This could make p-aminobenzoic acid a potential biomarker for the consumption of these foods. An aminobenzoic acid in which the amino group is para to the carboxy group.
CAS Number150-13-0
Structure
Thumb
Synonyms
SynonymSource
1-Amino-4-carboxybenzeneChEBI
4-Amino-benzoic acidChEBI
4-AminobenzoesaeureChEBI
4-CarboxyanilineChEBI
4-CarboxyphenylamineChEBI
ABEEChEBI
gamma-Aminobenzoic acidChEBI
p-AminobenzoesaeureChEBI
p-CarboxyanilineChEBI
p-CarboxyphenylamineChEBI
PABAChEBI
Para-aminobenzoic acidChEBI
4-Aminobenzoic acidKegg
p-AminobenzoateKegg
RVPaba lipstickKegg
4-Amino-benzoateGenerator
g-AminobenzoateGenerator
g-Aminobenzoic acidGenerator
gamma-AminobenzoateGenerator
Γ-aminobenzoateGenerator
Γ-aminobenzoic acidGenerator
Para-aminobenzoateGenerator
4-AminobenzoateGenerator
Acido p-aminobenzoicoHMDB
Acidum paraminobenzoicumHMDB
ActipolHMDB
AmbenHMDB
AminobenzoateHMDB
Aminobenzoic acidHMDB
Aniline-4-carboxylateHMDB
Aniline-4-carboxylic acidHMDB
Anti-chromotrichia factorHMDB
Anticanitic vitaminHMDB
Anticantic vitaminHMDB
Antichromotrichia factorHMDB
Bacterial vitamin H1HMDB
Chromotrichia factorHMDB
HacheminaHMDB
Kyselina p-aminobenzoovaHMDB
p-Amino-benzoateHMDB
p-Amino-benzoic acidHMDB
PABHMDB
PabacydHMDB
PabafilmHMDB
PabagelHMDB
PabamineHMDB
PabanolHMDB
PapacidumHMDB
ParaminolHMDB
ParanateHMDB
PotabaHMDB
RomavitHMDB
RvpabaHMDB
SunbrellaHMDB
Super shade by coppertoneHMDB
Trichochromogenic factorHMDB
Trochromogenic factorHMDB
Vitamin BXHMDB
Vitamin h'HMDB
4 Aminobenzoic acidHMDB
4 Aminobenzoic acid, potassium saltHMDB
EpitelplastHMDB
Jumer brand OF aminobenzoic acidHMDB
Medea brand OF aminobenzoic acidHMDB
ParaminanHMDB
4-Aminobenzoate, potassiumHMDB
Epit vitHMDB
Llorens brand OF aminobenzoic acidHMDB
PabasanHMDB
Potassium aminobenzoateHMDB
4-Aminobenzoic acid, potassium saltHMDB
Aminobenzoate, potassiumHMDB
Glenwood brand OF potassium aminobezoateHMDB
Llorens brand OF aminobenzoic acid sodium saltHMDB
Magnesium para-aminobenzoateHMDB
Potassium 4 aminobenzoateHMDB
Potassium 4-aminobenzoateHMDB
p Aminobenzoic acidHMDB
Para aminobenzoic acidHMDB
Para-aminobenzoate, magnesiumHMDB
p-Aminobenzoic acidChEBI
«gamma»-aminobenzoic acidbiospider
4-amino-BenzoateGenerator
4-AMINO-BENZOIC ACIDbiospider
Aminobenzoate acidbiospider
Aminobenzoic acid (usp)biospider
Aminobenzoic acid, parabiospider
Aminobenzoic acid, USANdb_source
Benzoic acid, 4-aminobiospider
Benzoic acid, 4-amino-biospider
Benzoic acid, p-amino-biospider
Gamma-aminobenzoatebiospider
Gamma-aminobenzoic acidbiospider
Kyselina P-aminobenzoovaHMDB
M-aminobenzonitrilebiospider
P-amino-benzoatebiospider
P-amino-benzoic acidbiospider
P-aminobenzoatebiospider
P-AminobenzoesaeureChEBI
P-aminobenzoic acidbiospider
P-carboxyanilinebiospider
P-carboxyphenylaminebiospider
Rvpaba lipstickbiospider
Rvpaba lipstick (TN)biospider
Sodium Aminobenzoate (4-Aminobenzoic Acid)biospider
Super shade BY coppertonebiospider
Vitamin H'db_source
γ-aminobenzoateGenerator
γ-aminobenzoic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility4.41 g/LALOGPS
logP0.78ALOGPS
logP0.8ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.77ChemAxon
pKa (Strongest Basic)2.69ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.01 m³·mol⁻¹ChemAxon
Polarizability13.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H7NO2
IUPAC name4-aminobenzoic acid
InChI IdentifierInChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
InChI KeyALYNCZNDIQEVRV-UHFFFAOYSA-N
Isomeric SMILESNC1=CC=C(C=C1)C(O)=O
Average Molecular Weight137.136
Monoisotopic Molecular Weight137.047678473
Classification
Description Belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids
Alternative Parents
Substituents
  • Aminobenzoic acid
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • 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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 61.31%; H 5.14%; N 10.21%; O 23.33%DFC
Melting PointMp 188-188.5°DFC
Boiling PointNot Available
Experimental Water Solubility6.11 mg/mL at 30 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP0.83HANSCH,C ET AL. (1995)
Experimental pKapKa2 4.87 (25°)DFC
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)splash10-00dr-8900000000-bface88b2e77a7dce6e1Spectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-24fa3ff739ff064312abSpectrum
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-8900000000-5b42adf83e422cffefb6Spectrum
GC-MS4-Aminobenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00yl-1960000000-b22b04854c131470802aSpectrum
GC-MS4-Aminobenzoic acid, 1 TMS, GC-MS Spectrumsplash10-0fkc-2900000000-dec9b6851633ff2c426cSpectrum
GC-MS4-Aminobenzoic acid, 2 TMS, GC-MS Spectrumsplash10-00yl-2890000000-b299bfaaed61286c2ff6Spectrum
GC-MS4-Aminobenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0079-9600000000-075c262f1e5d23ef097dSpectrum
GC-MS4-Aminobenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00yl-1960000000-b22b04854c131470802aSpectrum
GC-MS4-Aminobenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0fkc-2900000000-dec9b6851633ff2c426cSpectrum
GC-MS4-Aminobenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00yl-2890000000-b299bfaaed61286c2ff6Spectrum
GC-MS4-Aminobenzoic acid, non-derivatized, GC-MS Spectrumsplash10-00yl-1960000000-4d7d9e3e3a7a741c72caSpectrum
Predicted GC-MS4-Aminobenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kr-5900000000-8244277f60fc465369b8Spectrum
Predicted GC-MS4-Aminobenzoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-4900000000-299c72af4aa4008292bcSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ku-4900000000-ab0d2860a4f23e4fcad4Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00mo-9100000000-667a53f89529678400c7Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-0bbc34587525655f98efSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-8f6c193895f5adf391beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-78f63538a3011f036551Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-521edb7d484c452d0da3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7ae0035594587960bab7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-35088605171b150e8b08Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-3900000000-d67f9d252f758529a83cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-e4d34d9516fe889137f6Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-6900000000-387d1a3c2d588c6f8552Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r6-9200000000-9ef61d003f891b00406fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-eaf693e5f0cde39a548eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-7900000000-225973eab49386396fa9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-8f6c193895f5adf391beSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-78f63538a3011f036551Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-521edb7d484c452d0da3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7ae0035594587960bab7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9000000000-35088605171b150e8b08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-173f144fba431cca9164Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-ab3524c5aadc6fdc28cbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-67cea679b40b94c39ac0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-682d5d9d22372ece770bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-8d4bba3f647000005bb0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5d9b80bb0601c2f238c2Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID953
ChEMBL IDCHEMBL542
KEGG Compound IDC00568
Pubchem Compound ID978
Pubchem Substance IDNot Available
ChEBI ID30753
Phenol-Explorer IDNot Available
DrugBank IDDB02362
HMDB IDHMDB01392
CRC / DFC (Dictionary of Food Compounds) IDBQP21-U:BQP21-U
EAFUS ID164
Dr. Duke IDP-AMINOBENZOIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001401
HET IDPAB
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDp-Aminobenzoic acid
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
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti rickettsial33282 A substance that kills or slows the growth of bacteria.DUKE
anti thyroidDUKE
anti tubercular33282 A substance that kills or slows the growth of bacteria.DUKE
detoxicant50247 Any protective agent counteracting or neutralizing the action of poisons.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).