Record Information
Version1.0
Creation date2010-04-08 22:09:11 UTC
Update date2018-01-23 19:09:42 UTC
Primary IDFDB010553
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4-Methylenedioxybenzaldehyde
DescriptionFlavouring agent used in cherry and vanilla flavours. 3,4-Methylenedioxybenzaldehyde is found in pepper (spice), highbush blueberry, and vanilla.
CAS Number120-57-0
Structure
Thumb
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
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
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
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
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.