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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:10:18 UTC
Update Date2021-10-13 08:34:35 UTC
HMDB IDHMDB0041481
Secondary Accession Numbers
  • HMDB41481
Metabolite Identification
Common Name4-(3,4-Methylenedioxyphenyl)-2-butanone
Description4-(3,4-Methylenedioxyphenyl)-2-butanone belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. 4-(3,4-Methylenedioxyphenyl)-2-butanone is a sweet, candy, and cotton tasting compound. Based on a literature review very few articles have been published on 4-(3,4-Methylenedioxyphenyl)-2-butanone.
Structure
Data?1563863668
Synonyms
ValueSource
3,4-METHYLENEDIOXYBENZYL acetoneHMDB
3,4-MethylenedioxybenzylacetoneHMDB
3,4-METHYLENEDIOXYBENZYLIDENE acetoneHMDB
4-(1,3-Benzodioxol-5-yl)-2-butanoneHMDB
4-(1,3-Benzodioxol-5-yl)butan-2-oneHMDB
4-(3,4-Methylenedioxyphenyl)-2-butanone, 9ciHMDB
FEMA 2701HMDB
HeliotropylacetoneHMDB
Piperonyl acetoneHMDB
PiperonylacetoneHMDB
Piperonylidene acetoneHMDB
Chemical FormulaC11H12O3
Average Molecular Weight192.2112
Monoisotopic Molecular Weight192.07864425
IUPAC Name4-(2H-1,3-benzodioxol-5-yl)butan-2-one
Traditional Namepiperonyl acetone
CAS Registry Number55418-52-5
SMILES
CC(=O)CCC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C11H12O3/c1-8(12)2-3-9-4-5-10-11(6-9)14-7-13-10/h4-6H,2-3,7H2,1H3
InChI KeyTZJLGGWGVLADDN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Benzenoid
  • Ketone
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point55 °CNot Available
Boiling Point176.00 °C. @ 17.00 mm HgThe Good Scents Company Information System
Water Solubility892.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.148The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.53 g/LALOGPS
logP10(1.59) g/LALOGPS
logP10(2.01) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Acidic)19.59ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.28 m³·mol⁻¹ChemAxon
Polarizability20.38 ųChemAxon
Number of Rings2ChemAxon
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]+145.35531661259
DarkChem[M-H]-141.52731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-(3,4-Methylenedioxyphenyl)-2-butanoneCC(=O)CCC1=CC2=C(OCO2)C=C12513.9Standard polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanoneCC(=O)CCC1=CC2=C(OCO2)C=C11554.3Standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanoneCC(=O)CCC1=CC2=C(OCO2)C=C11597.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #1CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C1780.1Semi standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #1CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C1657.9Standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #2C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C1723.2Semi standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #2C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C1672.8Standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #1CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C2040.1Semi standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #1CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C1891.8Standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #2C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C1972.8Semi standard non polar33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #2C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C1886.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-4900000000-ac9b2fea1878e5144c7b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 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 - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Positive-QTOFsplash10-002f-0900000000-3525e495d33bc9c77b762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Positive-QTOFsplash10-004l-1900000000-02446f80e5cc5ec587452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Positive-QTOFsplash10-0ufr-6900000000-28a8fba4a202c974ba172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Negative-QTOFsplash10-0006-0900000000-40956cbf99ffbda4c1742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Negative-QTOFsplash10-0006-0900000000-60cdb8101c4256073c4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Negative-QTOFsplash10-00bc-2900000000-b7f00bb66442755efbe92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Negative-QTOFsplash10-0006-0900000000-3b8fc77e2c5dffca77652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Negative-QTOFsplash10-0006-0900000000-2a48ae6e31f71b3aae8d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Negative-QTOFsplash10-00ng-5900000000-0167e286bc12b3d6421a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Positive-QTOFsplash10-002o-0900000000-2ea49a60ba6fb44bd91f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Positive-QTOFsplash10-002r-0900000000-1eb2b873735859ee54122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Positive-QTOFsplash10-004l-8900000000-00d9f819c51027719d2f2021-09-24Wishart 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 IDFDB021444
KNApSAcK IDNot Available
Chemspider ID55934
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62098
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012851
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.. .