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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:39 UTC
Update Date2022-03-07 02:52:40 UTC
HMDB IDHMDB0030725
Secondary Accession Numbers
  • HMDB30725
Metabolite Identification
Common NameDillapiol
DescriptionDillapiol 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. Dillapiol is a spice and wood tasting compound. Dillapiol is found, on average, in the highest concentration within dills (Anethum graveolens) and cumins (Cuminum cyminum). Dillapiol has also been detected, but not quantified in, several different foods, such as corianders (Coriandrum sativum), fennels (Foeniculum vulgare), herbs and spices, and parsleys (Petroselinum crispum). This could make dillapiol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dillapiol.
Structure
Data?1563862028
Synonyms
ValueSource
5-Allyl 6,7-dimethoxy 1,3-benzodioxoleMeSH
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzeneMeSH
2-Methyl-5-(1-methylethenyl)-1,3-benzodioxoleMeSH
1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9ci)HMDB
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)-benzeneHMDB
1-Allyl-2,3-dimethoxy-4,5-methylenedioxybenzeneHMDB
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxoleHMDB
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9ciHMDB
6-Allyl-4,5-dimethoxy-1,3-benzodioxoleHMDB
Apiole (dill)HMDB
Dill apiolHMDB
Dill apioleHMDB
DillapioleHMDB
DillapiolKEGG
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Traditional Namedillapiol
CAS Registry Number484-31-1
SMILES
COC1=C(OC)C(CC=C)=CC2=C1OCO2
InChI Identifier
InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3
InChI KeyLIKYNOPXHGPMIH-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
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point29.5 °CNot Available
Boiling Point285.00 to 292.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility27.68 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.343 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.65 g/LALOGPS
logP2.33ALOGPS
logP2.38ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.04 m³·mol⁻¹ChemAxon
Polarizability22.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.56331661259
DarkChem[M-H]-148.93731661259
DeepCCS[M+H]+143.43830932474
DeepCCS[M-H]-140.91530932474
DeepCCS[M-2H]-176.51630932474
DeepCCS[M+Na]+152.05430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DillapiolCOC1=C(OC)C(CC=C)=CC2=C1OCO22433.1Standard polar33892256
DillapiolCOC1=C(OC)C(CC=C)=CC2=C1OCO21601.1Standard non polar33892256
DillapiolCOC1=C(OC)C(CC=C)=CC2=C1OCO21625.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dillapiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1930000000-759fd9f5828da82064eb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dillapiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-9660000000-7cd909d21ca4a4c8bb1e2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 10V, Positive-QTOFsplash10-00di-0190000000-65afe20a9d6ea8212ae42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 20V, Positive-QTOFsplash10-00dl-2490000000-a585b5b3566814b251fc2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 40V, Positive-QTOFsplash10-03g3-6900000000-e4d0d60144cac96a91bb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 10V, Negative-QTOFsplash10-00di-0090000000-a993c42f8477ed2928462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 20V, Negative-QTOFsplash10-00di-0690000000-969d0f40c3543ae561082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 40V, Negative-QTOFsplash10-0040-7900000000-72a37bef985f024191df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 10V, Positive-QTOFsplash10-00di-0090000000-434847f7ec0085e24b802021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 20V, Positive-QTOFsplash10-00di-0390000000-7be09d177fcf76fa1e712021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 40V, Positive-QTOFsplash10-0ldi-9520000000-f36f591d0e5c5b2747dd2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 10V, Negative-QTOFsplash10-00di-0090000000-e696c56af8179794e7ad2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 20V, Negative-QTOFsplash10-00di-0970000000-d9ab44e0dc7f91b8576e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dillapiol 40V, Negative-QTOFsplash10-03fr-9700000000-dc4990fb9e66012809052021-09-25Wishart LabView Spectrum
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
FooDB IDFDB002649
KNApSAcK IDC00002737
Chemspider ID9814
KEGG Compound IDC10449
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDillapiole
METLIN IDNot Available
PubChem Compound10231
PDB IDNot Available
ChEBI ID544678
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1019661
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.. .