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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:39 UTC
Update Date2019-07-23 06:07:08 UTC
HMDB IDHMDB0030725
Secondary Accession Numbers
  • HMDB30725
Metabolite Identification
Common NameDillapiol
DescriptionDillapiol, also known as apiole (dill), 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Dillapiol is a spice and wood tasting compound. Outside of the human body, Dillapiol is found, on average, in the highest concentration within dills and cumins. Dillapiol has also been detected, but not quantified in, several different foods, such as corianders, fennels, herbs and spices, and parsley. This could make dillapiol a potential biomarker for the consumption of these foods. Dillapiol is an organic chemical compound and essential oil commonly extracted from dill weed, though can be found in a variety of other plants.
Structure
Data?1563862028
Synonyms
ValueSource
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
2-Methyl-5-(1-methylethenyl)-1,3-benzodioxoleMeSH
1-Allyl-2,3-dimethoxy-4,5-(methylenedioxy)benzeneMeSH
5-Allyl 6,7-dimethoxy 1,3-benzodioxoleMeSH
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

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point29.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1930000000-759fd9f5828da82064ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-65afe20a9d6ea8212ae4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-2490000000-a585b5b3566814b251fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03g3-6900000000-e4d0d60144cac96a91bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-a993c42f8477ed292846Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-969d0f40c3543ae56108Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0040-7900000000-72a37bef985f024191dfSpectrum
MSMass Spectrum (Electron Ionization)splash10-00di-9660000000-7cd909d21ca4a4c8bb1eSpectrum
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 ID
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.. .