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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:55 UTC
Update Date2023-02-21 17:19:40 UTC
HMDB IDHMDB0030770
Secondary Accession Numbers
  • HMDB30770
Metabolite Identification
Common Name4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone
Description4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone, also known as 4'-hydroxy-3',5'-dimethyl-acetophenone or 4-acetyl-2-prenylphenol, 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. Based on a literature review very few articles have been published on 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone.
Structure
Data?1676999980
Synonyms
ValueSource
1-[4-Hydroxy-3-(3-methyl-2-butenyl)phenyl]ethanone, 9ciHMDB
4'-HYDROXY-3',5'-dimethyl-acetophenoneHMDB
4'-Hydroxy-3',5'-dimethylacetophenoneHMDB
4'-Hydroxy-3'-prenylacetophenoneHMDB
4-Acetyl-2-prenylphenolHMDB
4-H-3-(MB)APHMDB
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenoneMeSH
Chemical FormulaC13H16O2
Average Molecular Weight204.2649
Monoisotopic Molecular Weight204.115029756
IUPAC Name1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethan-1-one
Traditional Name1-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]ethanone
CAS Registry Number26932-05-8
SMILES
CC(C)=CCC1=C(O)C=CC(=C1)C(C)=O
InChI Identifier
InChI=1S/C13H16O2/c1-9(2)4-5-12-8-11(10(3)14)6-7-13(12)15/h4,6-8,15H,5H2,1-3H3
InChI KeyQJAPFSSVKIZTMR-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
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point93 - 94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility148.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP3.05ALOGPS
logP2.96ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.59ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.68 m³·mol⁻¹ChemAxon
Polarizability23.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.71731661259
DarkChem[M-H]-146.74731661259
DeepCCS[M+H]+147.62930932474
DeepCCS[M-H]-145.27130932474
DeepCCS[M-2H]-179.68830932474
DeepCCS[M+Na]+155.00230932474
AllCCS[M+H]+144.732859911
AllCCS[M+H-H2O]+140.632859911
AllCCS[M+NH4]+148.632859911
AllCCS[M+Na]+149.732859911
AllCCS[M-H]-148.032859911
AllCCS[M+Na-2H]-148.532859911
AllCCS[M+HCOO]-149.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenoneCC(C)=CCC1=C(O)C=CC(=C1)C(C)=O2613.1Standard polar33892256
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenoneCC(C)=CCC1=C(O)C=CC(=C1)C(C)=O1732.1Standard non polar33892256
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenoneCC(C)=CCC1=C(O)C=CC(=C1)C(C)=O1849.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone,1TMS,isomer #1CC(=O)C1=CC=C(O[Si](C)(C)C)C(CC=C(C)C)=C11860.2Semi standard non polar33892256
4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone,1TBDMS,isomer #1CC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)=C12114.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p6-4900000000-9cbfdba7ebf9a6361d982017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone GC-MS (1 TMS) - 70eV, Positivesplash10-03k9-6290000000-af3dd04185a385fada522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 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-Hydroxy-3-(3-methyl-2-butenyl)acetophenone , positive-QTOFsplash10-0002-1900000000-92dee8ca08bdfab6ffab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Negative-QTOFsplash10-06tb-0900000000-4c53b81469de62698ab02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Negative-QTOFsplash10-0002-0910000000-02bf584620735a5d0b6f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Positive-QTOFsplash10-0002-0910000000-8fdd6b705ab0193678b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Positive-QTOFsplash10-0002-0900000000-6b0fe0aaec869b1d340b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Negative-QTOFsplash10-0udi-0390000000-c625af71f47cfc663be42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Positive-QTOFsplash10-0a4i-0900000000-d5e7024da264cffccf262021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Positive-QTOFsplash10-0a4i-1690000000-4a14777a6cda9fcecda32016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Positive-QTOFsplash10-0cdj-4930000000-0296abc39fac52664ead2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Positive-QTOFsplash10-014i-9700000000-2065daeb365f421dc74a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Negative-QTOFsplash10-0udi-0190000000-c7b6432ab7a81d3136172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Negative-QTOFsplash10-0udi-0490000000-e0373680ed7ce6a9ee172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Negative-QTOFsplash10-000i-3900000000-1f2ecae9577454ad3bc42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Positive-QTOFsplash10-052b-2920000000-cfd053bee8ded4297efd2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Positive-QTOFsplash10-0006-9810000000-444554f46a35456aa6d02021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Positive-QTOFsplash10-052f-9800000000-4e793c744880d36928a52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 10V, Negative-QTOFsplash10-0udi-0090000000-7f5adf74d70ecbe2137c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 20V, Negative-QTOFsplash10-0udi-2590000000-d67c3f34fec59f1701de2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-3-(3-methyl-2-butenyl)acetophenone 40V, Negative-QTOFsplash10-014l-4900000000-2d63f142d0d87eb77fc82021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002705
KNApSAcK IDC00002699
Chemspider ID391219
KEGG Compound IDC10702
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound442916
PDB IDNot Available
ChEBI ID585101
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1822621
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.. .