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Showing Compound 3,4-Methylenedioxybenzaldehyde (FDB010553)

Record Information
Version1.0
Creation date2010-04-08 22:09:11 UTC
Update date2020-09-17 15:35:41 UTC
Primary IDFDB010553
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Methylenedioxybenzaldehyde
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 (https://doi.org/10.1002/14356007.a11_141).
CAS Number120-57-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
1,3-Benzodioxole-5-carboxaldehyde, 9CIdb_source
3,4-METHYLEN-DIOXY-BENZALDEHYDEbiospider
Benzaldehyde, 3,4-(methylenedioxy)-biospider
Blue pbiospider
Piperonal, 8CIdb_source
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
Chemical FormulaC8H6O3
IUPAC name2H-1,3-benzodioxole-5-carbaldehyde
InChI IdentifierInChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2
InChI KeySATCULPHIDQDRE-UHFFFAOYSA-N
Isomeric SMILES[H]C(=O)C1=CC2=C(OCO2)C=C1
Average Molecular Weight150.1314
Monoisotopic Molecular Weight150.031694058
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.00%; H 4.03%; O 31.97%DFC
Melting PointMp 37°DFC
Boiling PointBp15 140°DFC
Experimental Water Solubility3.5 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.05HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-deaf6988b3684d4c20e3Spectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udj-0900000000-b5bce0817d3b7da073b5Spectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udj-2900000000-dd3223a5400ccb92654cSpectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-f62030c087954cb17793Spectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0gvk-5900000000-8a0279ec82445d96e75aSpectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-deaf6988b3684d4c20e3Spectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udj-0900000000-b5bce0817d3b7da073b5Spectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0udj-2900000000-dd3223a5400ccb92654cSpectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0f6t-5900000000-f62030c087954cb17793Spectrum
GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, GC-MS Spectrumsplash10-0gvk-5900000000-8a0279ec82445d96e75aSpectrum
Predicted GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-5900000000-18459b3a00c1178d35a1Spectrum
Predicted GC-MS3,4-Methylenedioxybenzaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3,4-Methylenedioxybenzaldehyde, 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
ChemSpider ID13859497
ChEMBL IDCHEMBL271663
KEGG Compound IDC10812
Pubchem Compound ID8438
Pubchem Substance IDNot Available
ChEBI ID8240
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB32612
CRC / DFC (Dictionary of Food Compounds) IDFCW86-Y:FCW86-Y
EAFUS ID3060
Dr. Duke IDPIPERONAL|HELIOTROPIN
BIGG IDNot Available
KNApSAcK IDC00002666
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1005891
SuperScent ID8438
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
pediculicide38706 Substance used to treat lice (genus Pediculus) infestation.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
violet
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
heliotrope
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
flower
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.