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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:35:02 UTC
Update Date2023-02-21 17:23:38 UTC
HMDB IDHMDB0033813
Secondary Accession Numbers
  • HMDB33813
Metabolite Identification
Common Name3-(3,4-Methylenedioxyphenyl)propenal
Description3-(3,4-Methylenedioxyphenyl)propenal 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. 3-(3,4-Methylenedioxyphenyl)propenal has been detected, but not quantified in, several different foods, such as black tea, teas (Camellia sinensis), red tea, herbs and spices, and herbal tea. This could make 3-(3,4-methylenedioxyphenyl)propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(3,4-Methylenedioxyphenyl)propenal.
Structure
Data?1677000218
Synonyms
ValueSource
3,4-MethylenedioxycinnamaldehydeHMDB
3,4-Methylenedioxycinnamaldehyde, 8ciHMDB
3-(1,3-Benzodioxol-5-yl)-2-propenal, 9ciHMDB
3-(1,3-Benzodioxol-5-yl)acrylaldehydeHMDB
3-(3,4-Methylenedioxyphenyl)acroleinHMDB
PiperonylacroleinHMDB
PiperonylideneacetaldehydeHMDB
Chemical FormulaC10H8O3
Average Molecular Weight176.1687
Monoisotopic Molecular Weight176.047344122
IUPAC Name(2Z)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enal
Traditional Name(2Z)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enal
CAS Registry Number14756-00-4
SMILES
O=C\C=C/C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C10H8O3/c11-5-1-2-8-3-4-9-10(6-8)13-7-12-9/h1-6H,7H2/b2-1-
InChI KeyHZUFMSJUNLSDSZ-UPHRSURJSA-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
  • Styrene
  • Benzenoid
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point84 - 85 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1425 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.48 g/LALOGPS
logP1.79ALOGPS
logP1.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.9 m³·mol⁻¹ChemAxon
Polarizability17.66 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]+142.49731661259
DarkChem[M-H]-137.78231661259
DeepCCS[M+H]+137.65930932474
DeepCCS[M-H]-135.26330932474
DeepCCS[M-2H]-170.65730932474
DeepCCS[M+Na]+145.11630932474
AllCCS[M+H]+137.032859911
AllCCS[M+H-H2O]+132.532859911
AllCCS[M+NH4]+141.132859911
AllCCS[M+Na]+142.332859911
AllCCS[M-H]-137.232859911
AllCCS[M+Na-2H]-137.632859911
AllCCS[M+HCOO]-138.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-(3,4-Methylenedioxyphenyl)propenalO=C\C=C/C1=CC2=C(OCO2)C=C12578.7Standard polar33892256
3-(3,4-Methylenedioxyphenyl)propenalO=C\C=C/C1=CC2=C(OCO2)C=C11483.5Standard non polar33892256
3-(3,4-Methylenedioxyphenyl)propenalO=C\C=C/C1=CC2=C(OCO2)C=C11610.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1900000000-66f2647243c75d4dde1b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 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-(3,4-Methylenedioxyphenyl)propenal 10V, Positive-QTOFsplash10-004i-0900000000-9b66b1c2ef5b09ef6f872016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Positive-QTOFsplash10-004i-1900000000-75427a933490a5c638262016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Positive-QTOFsplash10-0pba-7900000000-24513de0b932e7ee1c442016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 10V, Negative-QTOFsplash10-004i-0900000000-ce45ddf94696c7737e492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Negative-QTOFsplash10-004i-0900000000-52f8e4472ba209a440592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Negative-QTOFsplash10-004j-2900000000-77fbed4965ba80679c472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 10V, Positive-QTOFsplash10-004i-0900000000-d0bb884df17a68411daa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Positive-QTOFsplash10-004i-0900000000-2b0cfa5a186f594dc39b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Positive-QTOFsplash10-004i-5900000000-68ff198bbdba3c5000932021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 10V, Negative-QTOFsplash10-004i-0900000000-4a803894b4fd0ab0e5a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Negative-QTOFsplash10-0002-0900000000-eafab4756929a1d839fd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Negative-QTOFsplash10-014j-3900000000-a5027aca8830808e8b6d2021-09-23Wishart 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+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 IDFDB011976
KNApSAcK IDC00034385
Chemspider ID4511077
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5355018
PDB IDNot Available
ChEBI ID173812
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1390361
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.. .