Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2019-11-26 02:55:36 UTC
Primary IDFDB000894
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetylsalicylic acid
DescriptionAspirin, also known as ASA or acetylsalicylate, belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid. Aspirin is an extremely weak basic (essentially neutral) compound (based on its pKa). Aspirin has been detected, but not quantified in, herbs and spices. This could make aspirin a potential biomarker for the consumption of these foods. Aspirin is a potentially toxic compound.
CAS Number50-78-2
Structure
Thumb
Synonyms
SynonymSource
2-(ACETYLOXY)benzoIC ACIDChEBI
2-Acetoxybenzenecarboxylic acidChEBI
2-Acetoxybenzoic acidChEBI
AcetylsalicylateChEBI
AcetylsalicylsaeureChEBI
Acide 2-(acetyloxy)benzoiqueChEBI
Acide acetylsalicyliqueChEBI
Acido acetilsalicilicoChEBI
Acidum acetylsalicylicumChEBI
ASAChEBI
AzetylsalizylsaeureChEBI
EasprinChEBI
O-Acetoxybenzoic acidChEBI
O-Acetylsalicylic acidChEBI
O-Carboxyphenyl acetateChEBI
Salicylic acid acetateChEBI
Acetylsalicylic acidKegg
AspalonKegg
DurlazaKegg
2-(ACETYLOXY)benzoateGenerator
2-AcetoxybenzenecarboxylateGenerator
2-AcetoxybenzoateGenerator
O-AcetoxybenzoateGenerator
O-AcetylsalicylateGenerator
O-Carboxyphenyl acetic acidGenerator
Salicylate acetateGenerator
Salicylic acid acetic acidGenerator
2-Carboxyphenyl acetateHMDB
AcenterineHMDB
AcetardHMDB
AceticylHMDB
AcetolHMDB
AcetonylHMDB
AcetophenHMDB
AcetosalHMDB
AcetosalinHMDB
AcetylinHMDB
AcetyonylHMDB
AcetysalHMDB
Acetysalicylic acidHMDB
AcylpyrinHMDB
AsatardHMDB
AspergumHMDB
AspirdropsHMDB
BenaspirHMDB
BialpiriniaHMDB
BufferinHMDB
CaprinHMDB
CardioaspirinaHMDB
EcolenHMDB
EcotrinHMDB
EmpirinHMDB
EndosprinHMDB
EndydolHMDB
O-(Acetyloxy)benzoateHMDB
O-(Acetyloxy)benzoic acidHMDB
PersistinHMDB
PharmacinHMDB
PolopirynaHMDB
PremaspinHMDB
RheumintablettenHMDB
RhodineHMDB
SalcetogenHMDB
SaletinHMDB
SalospirHMDB
SolprinHMDB
Solprin acidHMDB
SolpyronHMDB
TasprinHMDB
TemperalHMDB
ToldexHMDB
TriaminicinHMDB
MagnecylHMDB
PolopirinHMDB
SolupsanHMDB
ZorprinHMDB
DisprilHMDB
AloxiprimumHMDB
ColfaritHMDB
MicristinHMDB
Acid, acetylsalicylicHMDB
2-Acetyloxybenzoic acid, 9CIdb_source
AspirinChEBI
Aspirin, BAN, USANdb_source
o-Acetoxybenzoic acidmanual
o-Acetylsalicylic acidmanual
o-Carboxyphenyl acetatemanual
Salicylic acid acetate, 8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.46 g/LALOGPS
logP1.43ALOGPS
logP1.24ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.41ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.45 m³·mol⁻¹ChemAxon
Polarizability17.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H8O4
IUPAC name2-(acetyloxy)benzoic acid
InChI IdentifierInChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
InChI KeyBSYNRYMUTXBXSQ-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC1=CC=CC=C1C(O)=O
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
Classification
Description belongs to the class of organic compounds known as acylsalicylic acids. These are o-acylated derivatives of salicylic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAcylsalicylic acids
Alternative Parents
Substituents
  • Acylsalicylic acid
  • Phenol ester
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 60.00%; H 4.48%; O 35.52%DFC
Melting PointFp 118°DFC
Boiling PointNot Available
Experimental Water Solubility4.6 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.19HANSCH,C ET AL. (1995)
Experimental pKapKa 3.38 (25°, 1M KCl)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014l-2960000000-ffcb8d28ab7e460b0da8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-006w-2910000000-910e8ce2493a05870b33JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9400000000-64327d3bef0063cf4fe1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-0900000000-113943b65024522c1712JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-1590000000-7890c99ca2b0e2c4ff19JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-2960000000-ffcb8d28ab7e460b0da8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-006w-2910000000-910e8ce2493a05870b33JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006w-2900000000-253eb678a85f77d4ba61JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-8900000000-760033c820b78b9452edJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9830000000-b3fcef47ab2b2ba0e7d1JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kr-6900000000-324f46e8def1652ed4bfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-cdf64eaf75083da6f355JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-ee75806b6fb8a38fd697JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-00dl-9400000000-64327d3bef0063cf4fe1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-00di-0900000000-113943b65024522c1712JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-1900000000-bc50013edb10656e0aa4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-2900000000-8c55c1f8d7cb7f247a5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000l-9700000000-d475fd0478daf18a419aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-3daaf3c8697e17e67869JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-ee876bcdd1a5c7c229a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-cd4e1f8fe0a2bbc869f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-4dca49851b5b9fd03d1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kf-9000000000-4611655c6aff89d706ebJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014l-9000000000-4d636e2d7318b857528dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-1256ca04e4244fbc4a64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-2cae7e19320bfa1a03a0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-42f69c49b256900b7524JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-4860d5cbeeb9c31311ecJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-3900000000-cc185048e2a1bcc52124JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-96fcc874bfbf44a6ce6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-1900000000-8ea2ab1846fc78de4262JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkc-9700000000-53fc1f45243a05bf1c17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1900000000-421bc1739eeb6dced80aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-4900000000-1c7dec3a4993a5b23cd8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-81a6114ec99ac0f0f393JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00dl-6900000000-74f8a29aa18d0c3afe98JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID2157
ChEMBL IDCHEMBL25
KEGG Compound IDC01405
Pubchem Compound ID2244
Pubchem Substance IDNot Available
ChEBI ID15365
Phenol-Explorer IDNot Available
DrugBank IDDB00945
HMDB IDHMDB01879
CRC / DFC (Dictionary of Food Compounds) IDBLS47-M:BLS47-M
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID45400
KNApSAcK IDNot Available
HET IDAIN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAspirin
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
Pathways
NameSMPDB LinkKEGG Link
Acetylsalicylic Acid PathwaySMP00083 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference