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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:47 UTC
Update Date2018-03-12 22:11:17 UTC
HMDB IDHMDB0032612
Secondary Accession Numbers
  • HMDB32612
Metabolite Identification
Common Name3,4-Methylenedioxybenzaldehyde
DescriptionPiperonal, also known as heliotropin or piperonaldehyde, 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. Piperonal exists as a solid, slightly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, piperonal is primarily located in the cytoplasm. Piperonal exists in all eukaryotes, ranging from yeast to humans. Piperonal is a sweet, bitter, and coconut tasting compound that can be found in highbush blueberry, pepper (spice), and vanilla. This makes piperonal a potential biomarker for the consumption of these food products.
Structure
Thumb
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
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
DescriptionThis compound 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
  • Benzoyl
  • Aryl-aldehyde
  • Benzenoid
  • Oxacycle
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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
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)splash10-0f6t-5900000000-deaf6988b3684d4c20e3View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb17793View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e3View in MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b5View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb17793View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-5900000000-18459b3a00c1178d35a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5e34bc7a3df137e69deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-7dea1b5613bf810c5aa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l90-7900000000-0505f5c9e1fbdc94057bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b0c81ffa7cb223383909View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-7ff4ed41bbe2ad283edaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9700000000-abb6ae8bee74f8c6ae31View 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 IDFDB010553
KNApSAcK IDC00002666
Chemspider ID13859497
KEGG Compound IDC10812
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8438
PDB IDNot Available
ChEBI ID8240
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.. .