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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:57:18 UTC
Update Date2022-03-07 02:56:57 UTC
HMDB IDHMDB0041284
Secondary Accession Numbers
  • HMDB41284
Metabolite Identification
Common Name2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone
Description2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone, also known as 2-(2-methylpropanoyl)-4-prenylphloroglucinol or 2-(3',3'-dimethylallyl)-4-isobutyrylphloroglucinol, 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-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone has been detected, but not quantified in, alcoholic beverages. This could make 2-methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone.
Structure
Data?1563863645
Synonyms
ValueSource
2-(2-Methylpropanoyl)-4-prenylphloroglucinolChEBI
2-(2-Methylpropionyl)-4-prenylphloroglucinolChEBI
2-(3',3'-Dimethylallyl)-4-isobutyrylphloroglucinolChEBI
2-Isobutanoyl-4-prenylphloroglucinolChEBI
4-PrenylphlorisobutanophenoneChEBI
Dimethylallyl-phlorisobutyrophenoneChEBI
2-Methyl-1-(2,4,6-trihydroxy-3-(3-methyl2-butenyl)phenyl)-1-propanoneMeSH
UTX-53MeSH
Chemical FormulaC15H20O4
Average Molecular Weight264.3169
Monoisotopic Molecular Weight264.136159128
IUPAC Name2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
Traditional Name2-methyl-1-[2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]propan-1-one
CAS Registry Number35932-36-6
SMILES
CC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O
InChI Identifier
InChI=1S/C15H20O4/c1-8(2)5-6-10-11(16)7-12(17)13(15(10)19)14(18)9(3)4/h5,7,9,16-17,19H,6H2,1-4H3
InChI KeyIOBXAMCSYCVNET-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
  • Acylphloroglucinol derivative
  • Benzenetriol
  • Phloroglucinol derivative
  • Phenylpropane
  • Aryl alkyl ketone
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point166 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.65 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.79ALOGPS
logP4.89ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.82ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity75.85 m³·mol⁻¹ChemAxon
Polarizability28.86 ųChemAxon
Number of Rings1ChemAxon
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]+166.11531661259
DarkChem[M-H]-160.66931661259
DeepCCS[M+H]+167.58330932474
DeepCCS[M-H]-165.22530932474
DeepCCS[M-2H]-198.1130932474
DeepCCS[M+Na]+173.67630932474
AllCCS[M+H]+160.632859911
AllCCS[M+H-H2O]+157.032859911
AllCCS[M+NH4]+163.932859911
AllCCS[M+Na]+164.832859911
AllCCS[M-H]-164.632859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-165.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanoneCC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O3189.4Standard polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanoneCC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O1994.0Standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanoneCC(C)C(=O)C1=C(O)C=C(O)C(CC=C(C)C)=C1O2156.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TMS,isomer #1CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O2100.9Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O2100.8Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TMS,isomer #3CC(C)=CCC1=C(O)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C2076.8Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O2133.5Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C2099.1Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C2118.8Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C2197.1Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TBDMS,isomer #1CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O2338.2Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O2346.8Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,1TBDMS,isomer #3CC(C)=CCC1=C(O)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2332.8Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O2621.2Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TBDMS,isomer #2CC(C)=CCC1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2593.4Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,2TBDMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2611.2Semi standard non polar33892256
2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2839.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1090000000-db007320da1a609b6c602017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1100900000-06a36b45b3e6cca15dbc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 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-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Positive-QTOFsplash10-014i-1190000000-dd8776c84ddbc96a58492015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Positive-QTOFsplash10-00xr-6190000000-cbb3770a0613be6b81a12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Positive-QTOFsplash10-00xu-9400000000-9b4094f96a37da2b47a42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Negative-QTOFsplash10-03di-0190000000-b276ef77545bf0dc16ea2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Negative-QTOFsplash10-0006-3940000000-d0fd3234340acdba65472015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Negative-QTOFsplash10-00gl-6910000000-0e04604a367f1b06b18d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Negative-QTOFsplash10-03di-0090000000-16d43704d08f3756e03a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Negative-QTOFsplash10-03dl-0890000000-fc221df67d36f563f23e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Negative-QTOFsplash10-0006-3900000000-0933a7383709c57801ea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 10V, Positive-QTOFsplash10-014i-2090000000-1ccde9a1cf4567f922b02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 20V, Positive-QTOFsplash10-014i-3690000000-fd313b1b1d9d29b6296e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methyl-1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-1-propanone 40V, Positive-QTOFsplash10-014i-3920000000-9044653fe1e124d1504f2021-09-24Wishart 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 IDFDB021200
KNApSAcK IDC00057368
Chemspider ID24775685
KEGG Compound IDNot Available
BioCyc ID4-PRENYLPHLORISOBUTYROPHENONE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13411738
PDB IDNot Available
ChEBI ID134342
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1891081
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.. .