Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2019-11-27 17:03:56 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
AspalonKegg
Acetylsalicylic acidKegg
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
Bioavailability1ChemAxon
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 Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014l-2960000000-ffcb8d28ab7e460b0da8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-006w-2910000000-910e8ce2493a05870b33View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dl-9400000000-64327d3bef0063cf4fe1View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-00di-0900000000-113943b65024522c1712View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-1590000000-7890c99ca2b0e2c4ff19View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-2960000000-ffcb8d28ab7e460b0da8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-006w-2910000000-910e8ce2493a05870b33View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006w-2900000000-253eb678a85f77d4ba61View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-8900000000-760033c820b78b9452edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9830000000-b3fcef47ab2b2ba0e7d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kr-6900000000-324f46e8def1652ed4bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-cdf64eaf75083da6f355View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-ee75806b6fb8a38fd697View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-00dl-9400000000-64327d3bef0063cf4fe1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CI-B (Unknown) , Positivesplash10-00di-0900000000-113943b65024522c1712View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-1900000000-bc50013edb10656e0aa4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-2900000000-8c55c1f8d7cb7f247a5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000l-9700000000-d475fd0478daf18a419aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-3daaf3c8697e17e67869View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-ee876bcdd1a5c7c229a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-cd4e1f8fe0a2bbc869f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-4dca49851b5b9fd03d1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kf-9000000000-4611655c6aff89d706ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014l-9000000000-4d636e2d7318b857528dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-1256ca04e4244fbc4a64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-2cae7e19320bfa1a03a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-42f69c49b256900b7524View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ot-0900000000-4860d5cbeeb9c31311ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006t-3900000000-cc185048e2a1bcc52124View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-96fcc874bfbf44a6ce6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-1900000000-8ea2ab1846fc78de4262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fkc-9700000000-53fc1f45243a05bf1c17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-1900000000-421bc1739eeb6dced80aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-4900000000-1c7dec3a4993a5b23cd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-81a6114ec99ac0f0f393View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00dl-6900000000-74f8a29aa18d0c3afe98View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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