Showing Compound Card for Piperonal (CDB000662)

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Record Information
Version1.0
Created at2020-03-19 00:49:44 UTC
Updated at2020-12-07 19:07:38 UTC
CannabisDB IDCDB000662
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePiperonal
DescriptionPiperonal or 3,4-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. Piperonal is an organic compound which is commonly found in fragrances and flavors. Piperonal occurs naturally in various plants including dill, vanilla, violet flowers, and black pepper. Piperonal has been detected, but not quantified, in several different foods, such as highbush blueberries, pepper (spice), rabbiteye blueberries, and vanilla. Piperonal has a floral odor which is commonly described as being similar to that of vanillin or cherry. For this reason, it is commonly used in fragrances and artificial flavors ( Ref:DOI ). Piperonal has also been reported to be a volatile component of cannabis plants (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight150.13
Monoisotopic Molecular Weight150.0317
IUPAC Name2H-1,3-benzodioxole-5-carbaldehyde
Traditional Namepiperonal
CAS Registry Number120-57-0
SMILES
O=CC1=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 Point263 °CWikipedia
Water Solubility3.5 mg/mL at 20 °CNot Available
logP1.05Not Available
Predicted Properties
PropertyValueSource
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-deaf6988b3684d4c20e3Spectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0udj-0900000000-b5bce0817d3b7da073b5Spectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0udj-2900000000-dd3223a5400ccb92654cSpectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-f62030c087954cb17793Spectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0gvk-5900000000-8a0279ec82445d96e75aSpectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-deaf6988b3684d4c20e3Spectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0udj-0900000000-b5bce0817d3b7da073b5Spectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0udj-2900000000-dd3223a5400ccb92654cSpectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-f62030c087954cb17793Spectrum
GC-MSPiperonal, non-derivatized, GC-MS Spectrumsplash10-0gvk-5900000000-8a0279ec82445d96e75aSpectrum
Predicted GC-MSPiperonal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-5900000000-18459b3a00c1178d35a1Spectrum
Predicted GC-MSPiperonal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPiperonal, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-b5b6834400d9d66825442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0udi-0900000000-84dd85011e2ee53f24192020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-1900000000-62ac1d8f95baaaa86cdc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-2900000000-845d915e801880fe515e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0ukc-4900000000-a2da771088f9bd903b282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0fdo-7900000000-6d6138acd0b07ffaf80f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0006-9600000000-50b7e072efe444eab0462020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-9400000000-a00479fe5850665b281a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00kf-9100000000-d767f739422c110699e12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-014i-9000000000-2c58ea01cf6deb1fd0cb2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-014i-9000000000-e1b8a3928f36d4c767f02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-014i-9000000000-9a1a6e1587039d548c142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-014i-9000000000-8cba8d9c4f8d5695ce7f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-1900000000-54afeb3dfd71c9fcd6072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-014i-9000000000-02653bad35d9312486542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-791c4364189bf936d4c32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-e67da0571423f0e6b4b82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-00di-1900000000-94cc28f3d5f593c40e432020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-00di-1900000000-64a29a0890bb37965f422020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-e5e34bc7a3df137e69de2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-7dea1b5613bf810c5aa52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0l90-7900000000-0505f5c9e1fbdc94057b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-b0c81ffa7cb2233839092016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-7ff4ed41bbe2ad283eda2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9700000000-abb6ae8bee74f8c6ae312016-09-12View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032612
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]