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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:15 UTC
Update Date2023-02-21 17:21:56 UTC
HMDB IDHMDB0032336
Secondary Accession Numbers
  • HMDB32336
Metabolite Identification
Common Name3-Hydroxy-4-phenylbutan-2-one
Description3-Hydroxy-4-phenylbutan-2-one, also known as 2-butanone, 3-hydroxy-4-phenyl or 4-phenyl-3-hydroxybutan-2-one, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Based on a literature review very few articles have been published on 3-Hydroxy-4-phenylbutan-2-one.
Structure
Data?1677000116
Synonyms
ValueSource
2-Butanone, 3-hydroxy-4-phenylHMDB
4-Phenyl-3-hydroxybutan-2-oneHMDB
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name3-hydroxy-4-phenylbutan-2-one
Traditional Name3-hydroxy-4-phenylbutan-2-one
CAS Registry Number5355-63-5
SMILES
CC(=O)C(O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c1-8(11)10(12)7-9-5-3-2-4-6-9/h2-6,10,12H,7H2,1H3
InChI KeyQBCUUJGHWFKMDC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Acyloin
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.58 g/LALOGPS
logP0.98ALOGPS
logP1.51ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)13.33ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.01 m³·mol⁻¹ChemAxon
Polarizability17.81 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]+136.63531661259
DarkChem[M-H]-131.5431661259
DeepCCS[M+H]+133.88330932474
DeepCCS[M-H]-131.05330932474
DeepCCS[M-2H]-167.24630932474
DeepCCS[M+Na]+142.6730932474
AllCCS[M+H]+136.132859911
AllCCS[M+H-H2O]+131.732859911
AllCCS[M+NH4]+140.232859911
AllCCS[M+Na]+141.432859911
AllCCS[M-H]-136.732859911
AllCCS[M+Na-2H]-137.832859911
AllCCS[M+HCOO]-139.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-4-phenylbutan-2-oneCC(=O)C(O)CC1=CC=CC=C12237.5Standard polar33892256
3-Hydroxy-4-phenylbutan-2-oneCC(=O)C(O)CC1=CC=CC=C11316.5Standard non polar33892256
3-Hydroxy-4-phenylbutan-2-oneCC(=O)C(O)CC1=CC=CC=C11353.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-4-phenylbutan-2-one,1TMS,isomer #1CC(=O)C(CC1=CC=CC=C1)O[Si](C)(C)C1426.1Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,1TMS,isomer #2CC(O[Si](C)(C)C)=C(O)CC1=CC=CC=C11564.9Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,1TMS,isomer #3C=C(O[Si](C)(C)C)C(O)CC1=CC=CC=C11441.3Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C1600.7Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #1CC(O[Si](C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C1613.2Standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #2C=C(O[Si](C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C1492.9Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TMS,isomer #2C=C(O[Si](C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C1599.9Standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,1TBDMS,isomer #1CC(=O)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1669.0Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C(O)CC1=CC=CC=C11811.9Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)C(O)CC1=CC=CC=C11673.3Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2057.3Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2019.2Standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C1963.4Semi standard non polar33892256
3-Hydroxy-4-phenylbutan-2-one,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)C(CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C2007.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-d9ff230ad8227dc09f8f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9400000000-0387fd331cb4da6811112017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 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 - 3-Hydroxy-4-phenylbutan-2-one 10V, Positive-QTOFsplash10-014j-0900000000-87ba6264b385da4a43712015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Positive-QTOFsplash10-00kb-5900000000-eee31f6b3f93199787a52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Positive-QTOFsplash10-002f-9300000000-c7a29e18aa616a733c2a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 10V, Negative-QTOFsplash10-03di-1900000000-609dcbe4c5a60d549fb62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Negative-QTOFsplash10-02ml-4900000000-e644257bd3f96137fdbb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Negative-QTOFsplash10-0006-9300000000-4b4f7e92df5cff520b702015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 10V, Negative-QTOFsplash10-03di-3900000000-41261ce8c11c780044232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Negative-QTOFsplash10-0006-9000000000-8e87b2544a6e8cef47792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Negative-QTOFsplash10-0006-9200000000-e5489837cad018fa78df2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 10V, Positive-QTOFsplash10-0096-8900000000-43b816001002359713662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 20V, Positive-QTOFsplash10-0006-9200000000-828db0951cfecbbc1e2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-4-phenylbutan-2-one 40V, Positive-QTOFsplash10-0006-9100000000-0cbe88a7f712999d760f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H 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 IDFDB009609
KNApSAcK IDNot Available
Chemspider ID4934307
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6428929
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
3-Hydroxy-4-phenylbutan-2-one → [(3-oxo-1-phenylbutan-2-yl)oxy]sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-Hydroxy-4-phenylbutan-2-one → 3,4,5-trihydroxy-6-[(3-oxo-1-phenylbutan-2-yl)oxy]oxane-2-carboxylic aciddetails