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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:28:50 UTC
Update Date2023-02-21 17:23:32 UTC
HMDB IDHMDB0033723
Secondary Accession Numbers
  • HMDB33723
Metabolite Identification
Common Name4-(4-Hydroxyphenyl)-2-butanone
Description4-(4-Hydroxyphenyl)-2-butanone, also known as (p-hydroxybenzyl)acetone or 4-(3-oxobutyl)phenol, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. 4-(4-Hydroxyphenyl)-2-butanone is a sweet, berry, and floral tasting compound. 4-(4-Hydroxyphenyl)-2-butanone has been detected, but not quantified in, fruits and red raspberries (Rubus idaeus). This could make 4-(4-hydroxyphenyl)-2-butanone a potential biomarker for the consumption of these foods. 4-(4-Hydroxyphenyl)-2-butanone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 4-(4-Hydroxyphenyl)-2-butanone.
Structure
Data?1677000212
Synonyms
ValueSource
(p-Hydroxybenzyl)acetoneChEBI
1-(4-Hydroxyphenyl)-3-butanoneChEBI
1-(p-Hydroxyphenyl)-3-butanoneChEBI
4-(3-Oxobutyl)phenolChEBI
4-(p-Hydroxyphenyl)-2-butanoneChEBI
4-HydroxybenzylacetoneChEBI
p-Hydroxybenzyl acetoneChEBI
p-Hydroxyphenylbutan-2-oneChEBI
4-(4-Hydroxyphenyl)butan-2-oneMeSH
BetuligenolMeSH
OxyphenalonMeSH
p-HydroxybenzylacetoneMeSH
Raspberry ketoneMeSH
FEMA 2588HMDB
FrambinoneHMDB
P-HydroxyphenylbutanoneHMDB
Rasberry ketoneHMDB
RasketoneHMDB
RheosminHMDB
RheosmineHMDB
4-(4-Hydroxyphenyl)-2-butanoneChEBI
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name4-(4-hydroxyphenyl)butan-2-one
Traditional Nameraspberry ketone
CAS Registry Number5471-51-2
SMILES
CC(=O)CCC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
InChI KeyNJGBTKGETPDVIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point82.5 °CNot Available
Boiling Point200.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0 slightlyThe Good Scents Company Information System
LogP1.309 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.8 g/LALOGPS
logP2.08ALOGPS
logP2.08ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.5 m³·mol⁻¹ChemAxon
Polarizability18.02 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]+138.80231661259
DarkChem[M-H]-135.22231661259
DeepCCS[M+H]+135.830932474
DeepCCS[M-H]-132.83630932474
DeepCCS[M-2H]-169.77130932474
DeepCCS[M+Na]+145.30930932474
AllCCS[M+H]+135.332859911
AllCCS[M+H-H2O]+130.932859911
AllCCS[M+NH4]+139.432859911
AllCCS[M+Na]+140.632859911
AllCCS[M-H]-137.232859911
AllCCS[M+Na-2H]-138.332859911
AllCCS[M+HCOO]-139.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(4-Hydroxyphenyl)-2-butanoneCC(=O)CCC1=CC=C(O)C=C12703.1Standard polar33892256
4-(4-Hydroxyphenyl)-2-butanoneCC(=O)CCC1=CC=C(O)C=C11518.2Standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanoneCC(=O)CCC1=CC=C(O)C=C11567.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(4-Hydroxyphenyl)-2-butanone,1TMS,isomer #1CC(=O)CCC1=CC=C(O[Si](C)(C)C)C=C11612.6Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,1TMS,isomer #2CC(=CCC1=CC=C(O)C=C1)O[Si](C)(C)C1754.9Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,1TMS,isomer #3C=C(CCC1=CC=C(O)C=C1)O[Si](C)(C)C1773.2Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #1CC(=CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C1795.0Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #1CC(=CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C1713.6Standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C1717.6Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C1671.5Standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,1TBDMS,isomer #1CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11863.3Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,1TBDMS,isomer #2CC(=CCC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C1994.1Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,1TBDMS,isomer #3C=C(CCC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C1994.4Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #1CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2277.2Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #1CC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2211.2Standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2217.0Semi standard non polar33892256
4-(4-Hydroxyphenyl)-2-butanone,2TBDMS,isomer #2C=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C2141.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone EI-B (Non-derivatized)splash10-0a4i-5900000000-e86a807414e04733339d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone EI-B (Non-derivatized)splash10-0a4i-5900000000-e86a807414e04733339d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-7900000000-f17914de6993b20491562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone GC-MS (1 TMS) - 70eV, Positivesplash10-006x-7920000000-cb2a2ee41573305c6a882017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(4-Hydroxyphenyl)-2-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 - 4-(4-Hydroxyphenyl)-2-butanone 75V, Positive-QTOFsplash10-00di-5900000000-0a8b7fe2b9f1fb76ce6e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 90V, Positive-QTOFsplash10-00di-9700000000-a9d4506fbf302f416ea22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 15V, Positive-QTOFsplash10-00di-0900000000-1fd0e582b4ef7431f1312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 30V, Positive-QTOFsplash10-00di-0900000000-e2f8dc46c8f71782dd3a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 45V, Positive-QTOFsplash10-00di-1900000000-23fa756b8ca68a3f84c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 60V, Positive-QTOFsplash10-00di-2900000000-9db04c385775387df3fa2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Positive-QTOFsplash10-014j-0900000000-74c218754158b5095cc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Positive-QTOFsplash10-05mk-1900000000-574dbe1fc7ce6561ea622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Positive-QTOFsplash10-0zi3-9700000000-7faac7cc428fe0e255a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Negative-QTOFsplash10-03di-0900000000-2a84eaaa97fd7592296a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Negative-QTOFsplash10-03di-2900000000-7a3bca10c8cf4304c6e82016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Negative-QTOFsplash10-0a4l-9500000000-e985da2b00cefdf6bc1c2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Negative-QTOFsplash10-0a4i-9200000000-a1b1c874ab7b923bb7c32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Negative-QTOFsplash10-0a4i-9400000000-713daf098b2527154db22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Negative-QTOFsplash10-052f-9000000000-d9d01a460fd0c6839ef12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 10V, Positive-QTOFsplash10-066s-1900000000-df8baa8c079c2eea59742021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 20V, Positive-QTOFsplash10-0a4i-3900000000-aadb08876da6bfd67b202021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(4-Hydroxyphenyl)-2-butanone 40V, Positive-QTOFsplash10-004i-9300000000-041ace743c31c59af4512021-09-25Wishart 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 IDFDB011843
KNApSAcK IDC00041092
Chemspider ID20347
KEGG Compound IDNot Available
BioCyc IDCPD-8647
BiGG IDNot Available
Wikipedia LinkRaspberry_ketone
METLIN IDNot Available
PubChem Compound21648
PDB IDNot Available
ChEBI ID68656
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1020771
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.. .

Enzymes

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
4-(4-Hydroxyphenyl)-2-butanone → 3,4,5-trihydroxy-6-[4-(3-oxobutyl)phenoxy]oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
4-(4-Hydroxyphenyl)-2-butanone → [4-(3-oxobutyl)phenyl]oxidanesulfonic aciddetails