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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:47 UTC
Update Date2019-07-23 06:11:22 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Methylenedioxybenzaldehyde is a sweet, bitter, and coconut tasting compound. Outside of the human body, 3,4-Methylenedioxybenzaldehyde has been detected, but not quantified in, several different foods, such as highbush blueberries, pepper (spice), rabbiteye blueberries, and vanilla. This could make 3,4-methylenedioxybenzaldehyde a potential biomarker for the consumption of these foods.
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point37 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.5 mg/mL at 20 °CNot Available
LogP1.05Not Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e3Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb17793Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e3Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654cSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb17793Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-5900000000-18459b3a00c1178d35a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-b5b6834400d9d6682544Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-84dd85011e2ee53f2419Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-1900000000-62ac1d8f95baaaa86cdcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-2900000000-845d915e801880fe515eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0ukc-4900000000-a2da771088f9bd903b28Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0fdo-7900000000-6d6138acd0b07ffaf80fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0006-9600000000-50b7e072efe444eab046Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-9400000000-a00479fe5850665b281aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00kf-9100000000-d767f739422c110699e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-9000000000-2c58ea01cf6deb1fd0cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014i-9000000000-e1b8a3928f36d4c767f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-014i-9000000000-9a1a6e1587039d548c14Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9000000000-8cba8d9c4f8d5695ce7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-1900000000-54afeb3dfd71c9fcd607Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-02653bad35d931248654Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-791c4364189bf936d4c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-e67da0571423f0e6b4b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-1900000000-94cc28f3d5f593c40e43Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-1900000000-64a29a0890bb37965f42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5e34bc7a3df137e69deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-7dea1b5613bf810c5aa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l90-7900000000-0505f5c9e1fbdc94057bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b0c81ffa7cb223383909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-7ff4ed41bbe2ad283edaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9700000000-abb6ae8bee74f8c6ae31Spectrum
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 ID
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.. .