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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:33:41 UTC
Update Date2022-03-07 02:53:51 UTC
HMDB IDHMDB0033798
Secondary Accession Numbers
  • HMDB33798
Metabolite Identification
Common Name3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone
Description3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone, also known as phlorisovalerophenone, 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. 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone has been detected, but not quantified in, several different foods, such as wasabis (Wasabia japonica), pak choys (Brassica rapa var. chinensis), winter squashes (Cucurbita maxima), limes (Citrus aurantiifolia), and root vegetables. This could make 3-methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone.
Structure
Data?1563862461
Synonyms
ValueSource
PhlorisovalerophenoneChEBI
3-Methyl-1-(2,4,6-trihydroxyphenyl)butan-1-oneKegg
2',4',6'-Trihydroxy-3-methylbutyrophenone, 8ciHMDB
2,4,6-TrihydroxyisovalerophenoneHMDB
Chemical FormulaC11H14O4
Average Molecular Weight210.2265
Monoisotopic Molecular Weight210.089208936
IUPAC Name3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
Traditional Name3-methyl-1-(2,4,6-trihydroxyphenyl)butan-1-one
CAS Registry Number26103-97-9
SMILES
CC(C)CC(=O)C1=C(O)C=C(O)C=C1O
InChI Identifier
InChI=1S/C11H14O4/c1-6(2)3-8(13)11-9(14)4-7(12)5-10(11)15/h4-6,12,14-15H,3H2,1-2H3
InChI KeyVSDWHZGJGWMIRN-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
  • Butyrophenone
  • Benzenetriol
  • Phloroglucinol derivative
  • 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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point145 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility279.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.76 g/LALOGPS
logP2.11ALOGPS
logP3.35ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.01ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity56.18 m³·mol⁻¹ChemAxon
Polarizability21.22 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]+150.07431661259
DarkChem[M-H]-148.97931661259
DeepCCS[M+H]+152.79430932474
DeepCCS[M-H]-150.14730932474
DeepCCS[M-2H]-185.01730932474
DeepCCS[M+Na]+161.01330932474
AllCCS[M+H]+146.332859911
AllCCS[M+H-H2O]+142.332859911
AllCCS[M+NH4]+150.032859911
AllCCS[M+Na]+151.132859911
AllCCS[M-H]-147.532859911
AllCCS[M+Na-2H]-148.032859911
AllCCS[M+HCOO]-148.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanoneCC(C)CC(=O)C1=C(O)C=C(O)C=C1O2654.5Standard polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanoneCC(C)CC(=O)C1=C(O)C=C(O)C=C1O1764.1Standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanoneCC(C)CC(=O)C1=C(O)C=C(O)C=C1O2099.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,1TMS,isomer #1CC(C)CC(=O)C1=C(O)C=C(O)C=C1O[Si](C)(C)C1841.2Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,1TMS,isomer #2CC(C)CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1O1832.3Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,2TMS,isomer #1CC(C)CC(=O)C1=C(O[Si](C)(C)C)C=C(O)C=C1O[Si](C)(C)C1876.1Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,2TMS,isomer #2CC(C)CC(=O)C1=C(O)C=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C1842.9Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,3TMS,isomer #1CC(C)CC(=O)C1=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C1O[Si](C)(C)C1941.8Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,1TBDMS,isomer #1CC(C)CC(=O)C1=C(O)C=C(O)C=C1O[Si](C)(C)C(C)(C)C2086.0Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,1TBDMS,isomer #2CC(C)CC(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1O2083.1Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,2TBDMS,isomer #1CC(C)CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C1O[Si](C)(C)C(C)(C)C2359.0Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,2TBDMS,isomer #2CC(C)CC(=O)C1=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2329.2Semi standard non polar33892256
3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone,3TBDMS,isomer #1CC(C)CC(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C2604.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-8782ceb83df64880ef9a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone GC-MS (3 TMS) - 70eV, Positivesplash10-044i-9326500000-656817b218826d7617ac2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 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 - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone , positive-QTOFsplash10-0pb9-0900000000-acb41314f33574533a122017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 10V, Positive-QTOFsplash10-03di-1590000000-e4fbd3649b03ee2e383a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 20V, Positive-QTOFsplash10-0udi-3910000000-a840693f66d2858e94992015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 40V, Positive-QTOFsplash10-0udi-6900000000-a2865b99331b909bdc0f2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 10V, Negative-QTOFsplash10-0a4i-0390000000-e1c8ca9cc7f1f6c473ba2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 20V, Negative-QTOFsplash10-056r-2930000000-097fce40bb9093ff6b8e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 40V, Negative-QTOFsplash10-0059-7900000000-71672240b3fd39977ed92015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 10V, Negative-QTOFsplash10-0a4i-0190000000-e9d26e4f18bb8f0f25682021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 20V, Negative-QTOFsplash10-056r-1940000000-ff1d3754f5f342f97b602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 40V, Negative-QTOFsplash10-00kf-9200000000-aeb1c0891012deb61e1b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 10V, Positive-QTOFsplash10-03dl-9270000000-4cd0f738797008f2393c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 20V, Positive-QTOFsplash10-0006-9100000000-c8d68a00086c688e1f782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-(2,4,6-trihydroxyphenyl)-1-butanone 40V, Positive-QTOFsplash10-0udi-6900000000-fca53d9c62f23df586892021-09-25Wishart 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 IDFDB011960
KNApSAcK IDC00057297
Chemspider ID390036
KEGG Compound IDC07350
BioCyc ID3-METHYL-1-246-TRIHYDROXYPHENYLBUTAN
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441269
PDB IDNot Available
ChEBI ID15951
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1838451
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.. .