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Identification
YMDB IDYMDB01776
NamePiperonal
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
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).
Structure
Thumb
Synonyms
  • 1,3-Benzodioxole-5-carbaldehyde
  • 1,3-Benzodioxole-5-carboxaldehyde
  • 3, 4-(Methylenedioxy)benzaldehyde
  • 3, 4-Bis(methylenedioxy)benzaldehyde
  • 3,4-(Methylenedioxy)benzaldehyde
  • 3,4-Bis(methylenedioxy)benzaldehyde
  • 3,4-Dihydroxybenzaldehyde methylene ketal
  • 3,4-Methylene-dihydroxybenzaldehyde
  • 3,4-methylenedioxybenzaldehyde
  • 5-Formyl-1,3-benzodioxole
  • Benzaldehyde, 3,4-(methylenedioxy)-
  • Blue P
  • Dioxymethylene-protocatechuic aldehyde
  • Geliotropin
  • Heliotropin
  • Heliotropine
  • Heliotropine (Piperonal)
  • Piperanal
  • Piperonal
  • Piperonaldehyde
  • piperonyl aldehyde
  • Piperonylaldehyde
  • Protocatechuic aldehyde methylene ether
  • 1,3-Benzodioxole-5-carboxaldehyde, 9ci
  • 3,4-(Methylenedioxy)-benzaldehyde
  • 3,4-Dimethylenedioxybenzaldehyde
  • 3,4-METHYLEN-dioxy-benzaldehyde
  • Dioxymethylene protocatechuic aldehyde
  • FEMA 2911
  • Piperonal, 8ci
  • Heliotrin
CAS number120-57-0
WeightAverage: 150.1314
Monoisotopic: 150.031694058
InChI KeySATCULPHIDQDRE-UHFFFAOYSA-N
InChIInChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
IUPAC Name2H-1,3-benzodioxole-5-carbaldehyde
Traditional IUPAC Namepiperonal
Chemical FormulaC8H6O3
SMILESO=CC1=CC2=C(OCO2)C=C1
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
Physical Properties
StateSolid
Charge0
Melting point37 °C
Experimental Properties
PropertyValueReference
Water Solubility3.5 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.05 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BitterFDB010553
CoconutFDB010553
FlowerFDB010553
HeliotropeFDB010553
PowderyFDB010553
SweetFDB010553
VanillaFDB010553
VioletFDB010553
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb17793JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-deaf6988b3684d4c20e3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0udj-0900000000-b5bce0817d3b7da073b5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udj-2900000000-dd3223a5400ccb92654cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f6t-5900000000-f62030c087954cb17793JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0gvk-5900000000-8a0279ec82445d96e75aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fk9-5900000000-18459b3a00c1178d35a1JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-b5b6834400d9d6682544JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-84dd85011e2ee53f2419JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-1900000000-62ac1d8f95baaaa86cdcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-2900000000-845d915e801880fe515eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0ukc-4900000000-a2da771088f9bd903b28JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0fdo-7900000000-6d6138acd0b07ffaf80fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0006-9600000000-50b7e072efe444eab046JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-9400000000-a00479fe5850665b281aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00kf-9100000000-d767f739422c110699e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-9000000000-2c58ea01cf6deb1fd0cbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014i-9000000000-e1b8a3928f36d4c767f0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-014i-9000000000-9a1a6e1587039d548c14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9000000000-8cba8d9c4f8d5695ce7fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-1900000000-54afeb3dfd71c9fcd607JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-02653bad35d931248654JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-791c4364189bf936d4c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-e67da0571423f0e6b4b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-1900000000-94cc28f3d5f593c40e43JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-1900000000-64a29a0890bb37965f42JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5e34bc7a3df137e69deJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-7dea1b5613bf810c5aa5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l90-7900000000-0505f5c9e1fbdc94057bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b0c81ffa7cb223383909JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-7ff4ed41bbe2ad283edaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9700000000-abb6ae8bee74f8c6ae31JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID8240
HMDB IDHMDB0032612
Pubchem Compound ID8438
Kegg IDC10812
ChemSpider ID13859497
FOODB IDFDB010553
Wikipedia IDPiperonal
BioCyc IDNot Available