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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:10:20 UTC
Update Date2023-02-21 17:28:25 UTC
HMDB IDHMDB0040612
Secondary Accession Numbers
  • HMDB40612
Metabolite Identification
Common Name4-Acetyl-2(3H)-benzoxazolone
Description4-Acetyl-2(3H)-benzoxazolone belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group. 4-Acetyl-2(3H)-benzoxazolone is found, on average, in the highest concentration within corns (Zea mays). 4-Acetyl-2(3H)-benzoxazolone has also been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and fats and oils. This could make 4-acetyl-2(3H)-benzoxazolone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Acetyl-2(3H)-benzoxazolone.
Structure
Data?1677000505
Synonyms
ValueSource
4-Acetylbenzoxazolin-2-oneHMDB
Chemical FormulaC9H7NO3
Average Molecular Weight177.1568
Monoisotopic Molecular Weight177.042593095
IUPAC Name4-acetyl-2,3-dihydro-1,3-benzoxazol-2-one
Traditional Name4-acetyl-3H-1,3-benzoxazol-2-one
CAS Registry Number70735-79-4
SMILES
CC(=O)C1=C2NC(=O)OC2=CC=C1
InChI Identifier
InChI=1S/C9H7NO3/c1-5(11)6-3-2-4-7-8(6)10-9(12)13-7/h2-4H,1H3,(H,10,12)
InChI KeyFZAQRVWPQCXSPC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazoles
Sub ClassBenzoxazolones
Direct ParentBenzoxazolones
Alternative Parents
Substituents
  • Benzoxazolone
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzenoid
  • Azole
  • Oxazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketone
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point217 - 218 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3354 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.2 g/LALOGPS
logP1.02ALOGPS
logP0.89ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.4 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.67 m³·mol⁻¹ChemAxon
Polarizability16.79 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.39231661259
DarkChem[M-H]-135.29831661259
DeepCCS[M+H]+134.48530932474
DeepCCS[M-H]-132.08930932474
DeepCCS[M-2H]-166.96530932474
DeepCCS[M+Na]+141.42430932474
AllCCS[M+H]+135.832859911
AllCCS[M+H-H2O]+131.332859911
AllCCS[M+NH4]+140.032859911
AllCCS[M+Na]+141.232859911
AllCCS[M-H]-134.932859911
AllCCS[M+Na-2H]-135.232859911
AllCCS[M+HCOO]-135.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Acetyl-2(3H)-benzoxazoloneCC(=O)C1=C2NC(=O)OC2=CC=C12652.2Standard polar33892256
4-Acetyl-2(3H)-benzoxazoloneCC(=O)C1=C2NC(=O)OC2=CC=C11842.1Standard non polar33892256
4-Acetyl-2(3H)-benzoxazoloneCC(=O)C1=C2NC(=O)OC2=CC=C11705.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Acetyl-2(3H)-benzoxazolone,1TMS,isomer #1CC(=O)C1=CC=CC2=C1N([Si](C)(C)C)C(=O)O21813.5Semi standard non polar33892256
4-Acetyl-2(3H)-benzoxazolone,1TMS,isomer #1CC(=O)C1=CC=CC2=C1N([Si](C)(C)C)C(=O)O21843.6Standard non polar33892256
4-Acetyl-2(3H)-benzoxazolone,1TBDMS,isomer #1CC(=O)C1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)O22026.6Semi standard non polar33892256
4-Acetyl-2(3H)-benzoxazolone,1TBDMS,isomer #1CC(=O)C1=CC=CC2=C1N([Si](C)(C)C(C)(C)C)C(=O)O22043.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-2900000000-c2e3d7ec94f486a4ca642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 6V, Positive-QTOFsplash10-0ufr-0900000000-5202a5379e9ca936690d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Positive-QTOFsplash10-004i-0900000000-e4da8963e4cf5324f0782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Positive-QTOFsplash10-004i-0900000000-756537f4ff75c2cb6bc32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Positive-QTOFsplash10-03xu-1900000000-fbcf931425554c2864d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Negative-QTOFsplash10-004i-0900000000-faab935ec5f31e381b562017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Negative-QTOFsplash10-0059-0900000000-a1436c4ec8d3d2fb309c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Negative-QTOFsplash10-001i-1900000000-808b5c6ce7d271edcf152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Positive-QTOFsplash10-004i-0900000000-4441fde08ad1a50e1f592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Positive-QTOFsplash10-004i-0900000000-852d088d603a47a2d7332021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Positive-QTOFsplash10-05mo-5900000000-9dbe039a4255693a5f4e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 10V, Negative-QTOFsplash10-004j-0900000000-a4f24ec9f9880e1e900b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 20V, Negative-QTOFsplash10-004j-0900000000-7a4b54387bc05f6a6cbb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Acetyl-2(3H)-benzoxazolone 40V, Negative-QTOFsplash10-0a4j-2900000000-3ef3eeb26ad3ab1d43b52021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020403
KNApSAcK IDC00054437
Chemspider ID8165361
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9989779
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1884731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .