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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:40 UTC
Update Date2023-02-21 17:22:26 UTC
HMDB IDHMDB0032592
Secondary Accession Numbers
  • HMDB32592
Metabolite Identification
Common Name2'-Hydroxy-5'-methylacetophenone
Description2'-Hydroxy-5'-methylacetophenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 2'-Hydroxy-5'-methylacetophenone is a sweet, floral, and heavy tasting compound. 2'-Hydroxy-5'-methylacetophenone has been detected, but not quantified in, a few different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 2'-hydroxy-5'-methylacetophenone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2'-Hydroxy-5'-methylacetophenone.
Structure
Data?1677000145
Synonyms
ValueSource
1-(2-Hydroxy-5-methylphenyl)-ethanoneHMDB
1-(2-Hydroxy-5-methylphenyl)ethanoneHMDB
1-(2-Hydroxy-5-methylphenyl)ethanone, 9ciHMDB
1-Hydroxy-2-acetyl-4-methylbenzeneHMDB
2'-Hydroxy-5'-methyl-acetophenoneHMDB
2-Acetyl-4-methylphenolHMDB
2-Acetyl-P-cresolHMDB
2-Hydroxy-5-methylacetophenoneHMDB
Methyl 6-hydroxy-m-tolyl ketoneHMDB
O-Acetyl-P-cresolHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
IUPAC Name1-(2-hydroxy-5-methylphenyl)ethan-1-one
Traditional Name2-acetyl-4-methylphenol
CAS Registry Number1450-72-2
SMILES
CC(=O)C1=C(O)C=CC(C)=C1
InChI Identifier
InChI=1S/C9H10O2/c1-6-3-4-9(11)8(5-6)7(2)10/h3-5,11H,1-2H3
InChI KeyYNPDFBFVMJNGKZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Acetophenone
  • Aryl alkyl ketone
  • P-cresol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point50 °CNot Available
Boiling Point210.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2038 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.941 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.48 g/LALOGPS
logP1.91ALOGPS
logP2.39ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.5ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.48 m³·mol⁻¹ChemAxon
Polarizability16.03 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.27331661259
DarkChem[M-H]-131.06931661259
DeepCCS[M+H]+134.87230932474
DeepCCS[M-H]-131.41230932474
DeepCCS[M-2H]-168.86930932474
DeepCCS[M+Na]+144.40730932474
AllCCS[M+H]+129.632859911
AllCCS[M+H-H2O]+125.032859911
AllCCS[M+NH4]+133.932859911
AllCCS[M+Na]+135.232859911
AllCCS[M-H]-129.032859911
AllCCS[M+Na-2H]-130.332859911
AllCCS[M+HCOO]-131.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2'-Hydroxy-5'-methylacetophenoneCC(=O)C1=C(O)C=CC(C)=C11834.9Standard polar33892256
2'-Hydroxy-5'-methylacetophenoneCC(=O)C1=C(O)C=CC(C)=C11276.4Standard non polar33892256
2'-Hydroxy-5'-methylacetophenoneCC(=O)C1=C(O)C=CC(C)=C11266.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2'-Hydroxy-5'-methylacetophenone,1TMS,isomer #1CC(=O)C1=CC(C)=CC=C1O[Si](C)(C)C1446.0Semi standard non polar33892256
2'-Hydroxy-5'-methylacetophenone,1TBDMS,isomer #1CC(=O)C1=CC(C)=CC=C1O[Si](C)(C)C(C)(C)C1705.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-5'-methylacetophenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pc9-2900000000-e951f0957eb44bc9f3132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-5'-methylacetophenone GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9760000000-43f0f53ae58ddd85aa912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2'-Hydroxy-5'-methylacetophenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Positive-QTOFsplash10-0udi-0900000000-2bedbd136aa1bc56b6582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Positive-QTOFsplash10-0udi-1900000000-20831b6c52d65cce72922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Positive-QTOFsplash10-0kau-7900000000-07b8d20195dcd7ade99e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Negative-QTOFsplash10-0002-0900000000-75c3d53ce83ee89c3d912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Negative-QTOFsplash10-0002-0900000000-5102a3f8aa849eb480342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Negative-QTOFsplash10-0a4i-5900000000-bc0c006306db2d57909d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Positive-QTOFsplash10-0ue9-0900000000-1b7e40a5a029f99a026b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Positive-QTOFsplash10-0a7l-6900000000-837d6f16e4f4e3de02dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Positive-QTOFsplash10-004i-9300000000-fb8d5f4815934be81adf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 10V, Negative-QTOFsplash10-0002-0900000000-e0b12c10ffeec106d7592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 20V, Negative-QTOFsplash10-0a4i-0900000000-b8a70d97cc6153760dcc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2'-Hydroxy-5'-methylacetophenone 40V, Negative-QTOFsplash10-053s-9700000000-a106c9acc126ee48d4202021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB010529
KNApSAcK IDNot Available
Chemspider ID14340
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15068
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1158081
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.. .