Record Information
Version1.0
Creation date2010-04-08 22:04:48 UTC
Update date2015-10-09 22:29:28 UTC
Primary IDFDB001037
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Aminobenzoic acid
DescriptionListed in the EAFUS Food Additive Database (Jan. 2001) but with no reported use 4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA) is an organic compound with the molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxyl group.; 4-Aminobenzoic acid, para-aminobenzoic acid, or simply PABA, is an organic compound with molecular formula C7H7NO2. PABA is a white crystalline substance that is only slightly soluble in water. It consists of a benzene ring substituted with an amino group and a carboxylic acid.; A member of the vitamin B complex. It used to be a common sunscreening agent until found to also be a sensitizer. The potassium salt is used therapeutically in fibrotic skin disorders.; PABA is an essential nutrient for some bacteria and is sometimes called Vitamin Bx. However, PABA is not essential for humans and it varies in its activity from other B vitamins. Although humans lack the ability to synthesize folate from PABA, it is sometimes marketed as an essential nutrient under the premise that it can stimulate intestinal bacteria.; PABA is an essential nutrient for some bacteria and is sometimes called Vitamin Bx. In humans, PABA is normally made by E. coli in the colon and therefore PABA from food is not normally essential to human health. PABA is therefore not officially classified as a vitamin. PABA is an intermediate in bacterial synthesis of folate. Although humans lack the ability to synthesize folate from PABA, that is also normally done by E. coli. PABA is sometimes marketed as an essential nutrient for use whenever normal PABA synthesis by intestinal bacteria is insufficient.
CAS Number150-13-0
Structure
Thumb
Synonyms
SynonymSource
«gamma»-aminobenzoic acidbiospider
1-Amino-4-carboxybenzenebiospider
4-amino-BenzoateGenerator
4-AMINO-BENZOIC ACIDbiospider
4-Aminobenzoatebiospider
4-AminobenzoesaeureChEBI
4-Carboxyanilinebiospider
4-Carboxyphenylaminebiospider
ABEEbiospider
Acido p-aminobenzoicobiospider
Acidum paraminobenzoicumbiospider
Actipolbiospider
Ambenbiospider
Aminobenzoatebiospider
Aminobenzoate acidbiospider
Aminobenzoic acidbiospider
Aminobenzoic acid (usp)biospider
Aminobenzoic acid, parabiospider
Aminobenzoic acid, USANdb_source
Aniline-4-carboxylatebiospider
Aniline-4-carboxylic acidbiospider
Anti-chromotrichia factorbiospider
Anticanitic vitaminbiospider
Anticantic vitaminbiospider
Antichromotrichia factorbiospider
Bacterial vitamin H1biospider
Benzoic acid, 4-aminobiospider
Benzoic acid, 4-amino-biospider
Benzoic acid, p-amino-biospider
Chromotrichia factorbiospider
g-AminobenzoateGenerator
g-Aminobenzoic acidGenerator
Gamma-aminobenzoatebiospider
Gamma-aminobenzoic acidbiospider
Hacheminabiospider
Kyselina P-aminobenzoovaHMDB
M-aminobenzonitrilebiospider
P-amino-benzoatebiospider
P-amino-benzoic acidbiospider
P-aminobenzoatebiospider
P-AminobenzoesaeureChEBI
P-aminobenzoic acidbiospider
P-carboxyanilinebiospider
P-carboxyphenylaminebiospider
PABbiospider
PABAdb_source
Pabacydbiospider
Pabafilmbiospider
Pabagelbiospider
Pabaminebiospider
Pabanolbiospider
Papacidumbiospider
Para-aminobenzoatebiospider
Para-aminobenzoic acidbiospider
Paraminolbiospider
Paranatebiospider
Potababiospider
Romavitbiospider
Rvpababiospider
Rvpaba lipstickbiospider
Rvpaba lipstick (TN)biospider
Sodium Aminobenzoate (4-Aminobenzoic Acid)biospider
Sunbrellabiospider
Super shade BY coppertonebiospider
Trichochromogenic factorbiospider
Trochromogenic factorbiospider
Vitamin BXbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 KeyInChIKey=ALYNCZNDIQEVRV-UHFFFAOYSA-N
Isomeric SMILESNC1=CC=C(C=C1)C(O)=O
Average Molecular Weight137
Monoisotopic Molecular Weight137
Classification
DescriptionThis compound 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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00yl-1960000000-b22b04854c131470802aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fkc-2900000000-dec9b6851633ff2c426cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00yl-2890000000-b299bfaaed61286c2ff6View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-9600000000-075c262f1e5d23ef097dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00yl-1960000000-b22b04854c131470802aView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0fkc-2900000000-dec9b6851633ff2c426cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00yl-2890000000-b299bfaaed61286c2ff6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00yl-1960000000-4d7d9e3e3a7a741c72caView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kr-5900000000-8244277f60fc465369b8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-4900000000-299c72af4aa4008292bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ku-4900000000-ab0d2860a4f23e4fcad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00mo-9100000000-667a53f89529678400c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-0bbc34587525655f98efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-8f6c193895f5adf391beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-78f63538a3011f036551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-521edb7d484c452d0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-7ae0035594587960bab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00kf-9000000000-35088605171b150e8b08View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-3900000000-d67f9d252f758529a83cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-00di-1900000000-e4d34d9516fe889137f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-6900000000-387d1a3c2d588c6f8552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r6-9200000000-9ef61d003f891b00406fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-eaf693e5f0cde39a548eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-000i-7900000000-225973eab49386396fa9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-8f6c193895f5adf391beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-78f63538a3011f036551View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-521edb7d484c452d0da3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-7ae0035594587960bab7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00kf-9000000000-35088605171b150e8b08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-173f144fba431cca9164View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-ab3524c5aadc6fdc28cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9200000000-67cea679b40b94c39ac0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-682d5d9d22372ece770bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-8d4bba3f647000005bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5d9b80bb0601c2f238c2View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00dr-8900000000-bface88b2e77a7dce6e1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).