Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2019-11-27 17:07:15 UTC
Primary IDFDB002649
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. Dillapiol is found, on average, in the highest concentration in 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.
CAS Number484-31-1
Structure
Thumb
Synonyms
SynonymSource
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
1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)-biospider
1,3-Benzodioxole, 4,5-dimethoxy-6-(2-propenyl)- (9CI)biospider
4,5-Dimethoxy-6-(2-propenyl)-1,3-benzodioxole, 9CIdb_source
Benzene, 1-allyl-2,3-dimethoxy-4,5-(methylenedioxy)-biospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H14O4
IUPAC name4,5-dimethoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(OC)C(CC=C)=CC2=C1OCO2
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
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
  • 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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 64.85%; H 6.35%; O 28.80%DFC
Melting PointMp 29.5°DFC
Boiling PointBp0.8 100°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn25D 1.5278DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-1930000000-759fd9f5828da82064ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-65afe20a9d6ea8212ae4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-2490000000-a585b5b3566814b251fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03g3-6900000000-e4d0d60144cac96a91bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-a993c42f8477ed292846View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-969d0f40c3543ae56108View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0040-7900000000-72a37bef985f024191dfView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-9660000000-7cd909d21ca4a4c8bb1eView in MoNA
ChemSpider ID9814
ChEMBL IDCHEMBL470874
KEGG Compound IDC10449
Pubchem Compound ID10231
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30725
CRC / DFC (Dictionary of Food Compounds) IDCMX09-T:CMX09-T
EAFUS IDNot Available
Dr. Duke IDDILLAPIOLE|DILLAPIOL
BIGG IDNot Available
KNApSAcK IDC00002737
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID484-31-1
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDillapiol
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
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
insecticide24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
molluscicide33904 A substance used to destroy pests of the phylum Mollusca.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wood
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
spice
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
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.