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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:28:50 UTC
Update Date2018-03-12 22:09:36 UTC
HMDB IDHMDB0033723
Secondary Accession Numbers
  • HMDB33723
Metabolite Identification
Common Name4-(4-Hydroxyphenyl)-2-butanone
Description4-(4-Hydroxyphenyl)-2-butanone is found in fruits. 4-(4-Hydroxyphenyl)-2-butanone is isolated from raspberries (Rubus idaeus), rhubarb (Rheum species), European cranberry (Vaccinium oxycoccus), blackberry, loganberry and redcurrants. 4-(4-Hydroxyphenyl)-2-butanone is an important flavour ingredient.
Structure
Thumb
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-oneHMDB
BetuligenolHMDB
FEMA 2588HMDB
FrambinoneHMDB
OxyphenalonHMDB
P-HydroxyphenylbutanoneHMDB
Rasberry ketoneHMDB
RasketoneHMDB
Raspberry ketoneHMDB
RheosminHMDB
RheosmineHMDB
P-HydroxybenzylacetoneMeSH
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
DescriptionThis compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point82.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-e86a807414e04733339dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-e86a807414e04733339dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-7900000000-f17914de6993b2049156View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-7920000000-cb2a2ee41573305c6a88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-74c218754158b5095cc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-1900000000-574dbe1fc7ce6561ea62View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi3-9700000000-7faac7cc428fe0e255a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-2a84eaaa97fd7592296aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2900000000-7a3bca10c8cf4304c6e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9500000000-e985da2b00cefdf6bc1cView in MoNA
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
FoodDB IDFDB011843
KNApSAcK IDNot Available
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
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