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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:47 UTC
Update Date2022-03-07 02:53:24 UTC
HMDB IDHMDB0032612
Secondary Accession Numbers
  • HMDB32612
Metabolite Identification
Common Name3,4-Methylenedioxybenzaldehyde
Description3,4-Methylenedioxybenzaldehyde, also known as heliotropin or piperonyl aldehyde, 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. 3,4-Methylenedioxybenzaldehyde is a sweet, bitter, and coconut tasting compound. 3,4-Methylenedioxybenzaldehyde has been detected, but not quantified in, several different foods, such as highbush blueberries (Vaccinium corymbosum), pepper (spice), rabbiteye blueberries (Vaccinium virgatum), and vanillas (Vanilla). This could make 3,4-methylenedioxybenzaldehyde a potential biomarker for the consumption of these foods. 3,4-Methylenedioxybenzaldehyde 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 3,4-Methylenedioxybenzaldehyde.
Structure
Data?1563862282
Synonyms
ValueSource
1,3-Benzodioxole-5-carboxaldehydeChEBI
3,4-(Methylenedioxy)benzaldehydeChEBI
3,4-Dihydroxybenzaldehyde methylene ketalChEBI
5-Formyl-1,3-benzodioxoleChEBI
HeliotropinChEBI
HeliotropineChEBI
PiperonaldehydeChEBI
Piperonyl aldehydeChEBI
PiperonylaldehydeChEBI
Protocatechuic aldehyde methylene etherChEBI
1,3-Benzodioxole-5-carbaldehydeHMDB
1,3-Benzodioxole-5-carboxaldehyde, 9ciHMDB
3, 4-(Methylenedioxy)benzaldehydeHMDB
3, 4-Bis(methylenedioxy)benzaldehydeHMDB
3,4-(Methylenedioxy)-benzaldehydeHMDB
3,4-Bis(methylenedioxy)benzaldehydeHMDB
3,4-DimethylenedioxybenzaldehydeHMDB
3,4-METHYLEN-dioxy-benzaldehydeHMDB
3,4-Methylene-dihydroxybenzaldehydeHMDB
Blue PHMDB
Dioxymethylene protocatechuic aldehydeHMDB
Dioxymethylene-protocatechuic aldehydeHMDB
FEMA 2911HMDB
GeliotropinHMDB
Heliotropine (piperonal)HMDB
PiperanalHMDB
PiperonalHMDB
Piperonal, 8ciHMDB
3,4-MethylenedioxybenzaldehydeChEBI
HeliotrinMeSH
Chemical FormulaC8H6O3
Average Molecular Weight150.1314
Monoisotopic Molecular Weight150.031694058
IUPAC Name2H-1,3-benzodioxole-5-carbaldehyde
Traditional Namepiperonal
CAS Registry Number120-57-0
SMILES
[H]C(=O)C1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
InChI KeySATCULPHIDQDRE-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
  • Aryl-aldehyde
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point37 °CNot Available
Boiling Point263.00 to 265.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3.5 mg/mL at 20 °CNot Available
LogP1.05Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility8.28 g/LALOGPS
logP0.79ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.41 m³·mol⁻¹ChemAxon
Polarizability14.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+130.13431661259
DarkChem[M-H]-127.64931661259
DeepCCS[M+H]+132.23830932474
DeepCCS[M-H]-129.91230932474
DeepCCS[M-2H]-165.28930932474
DeepCCS[M+Na]+139.74830932474
AllCCS[M+H]+130.332859911
AllCCS[M+H-H2O]+125.632859911
AllCCS[M+NH4]+134.732859911
AllCCS[M+Na]+136.032859911
AllCCS[M-H]-127.732859911
AllCCS[M+Na-2H]-128.532859911
AllCCS[M+HCOO]-129.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4-Methylenedioxybenzaldehyde[H]C(=O)C1=CC2=C(OCO2)C=C12346.2Standard polar33892256
3,4-Methylenedioxybenzaldehyde[H]C(=O)C1=CC2=C(OCO2)C=C11304.1Standard non polar33892256
3,4-Methylenedioxybenzaldehyde[H]C(=O)C1=CC2=C(OCO2)C=C11323.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb177932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654c2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb177932018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-5900000000-18459b3a00c1178d35a12016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4-Methylenedioxybenzaldehyde 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 - 3,4-Methylenedioxybenzaldehyde Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-b5b6834400d9d66825442020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 1V, positive-QTOFsplash10-0udi-0900000000-84dd85011e2ee53f24192020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 2V, positive-QTOFsplash10-0udi-1900000000-62ac1d8f95baaaa86cdc2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 2V, positive-QTOFsplash10-0udi-2900000000-845d915e801880fe515e2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 3V, positive-QTOFsplash10-0ukc-4900000000-a2da771088f9bd903b282020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 3V, positive-QTOFsplash10-0fdo-7900000000-6d6138acd0b07ffaf80f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 3V, positive-QTOFsplash10-0006-9600000000-50b7e072efe444eab0462020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 4V, positive-QTOFsplash10-0006-9400000000-a00479fe5850665b281a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 5V, positive-QTOFsplash10-00kf-9100000000-d767f739422c110699e12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 6V, positive-QTOFsplash10-014i-9000000000-2c58ea01cf6deb1fd0cb2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 8V, positive-QTOFsplash10-014i-9000000000-e1b8a3928f36d4c767f02020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 9V, positive-QTOFsplash10-014i-9000000000-9a1a6e1587039d548c142020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 11V, positive-QTOFsplash10-014i-9000000000-8cba8d9c4f8d5695ce7f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOFsplash10-00di-1900000000-54afeb3dfd71c9fcd6072020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOFsplash10-014i-9000000000-02653bad35d9312486542020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOFsplash10-004i-9000000000-791c4364189bf936d4c32020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde n/a 10V, positive-QTOFsplash10-0006-9000000000-e67da0571423f0e6b4b82020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 0V, positive-QTOFsplash10-00di-1900000000-94cc28f3d5f593c40e432020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde Orbitrap 1V, positive-QTOFsplash10-00di-1900000000-64a29a0890bb37965f422020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 10V, Positive-QTOFsplash10-0udi-0900000000-e5e34bc7a3df137e69de2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 20V, Positive-QTOFsplash10-0udi-0900000000-7dea1b5613bf810c5aa52016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 40V, Positive-QTOFsplash10-0l90-7900000000-0505f5c9e1fbdc94057b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 10V, Negative-QTOFsplash10-0002-0900000000-b0c81ffa7cb2233839092016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 20V, Negative-QTOFsplash10-0002-0900000000-7ff4ed41bbe2ad283eda2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4-Methylenedioxybenzaldehyde 40V, Negative-QTOFsplash10-0002-9700000000-abb6ae8bee74f8c6ae312016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart 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 IDFDB010553
KNApSAcK IDC00002666
Chemspider ID13859497
KEGG Compound IDC10812
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPiperonal
METLIN IDNot Available
PubChem Compound8438
PDB IDNot Available
ChEBI ID8240
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1005891
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.. .