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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:32:18 UTC
Update Date2019-07-23 06:14:18 UTC
HMDB IDHMDB0033776
Secondary Accession Numbers
  • HMDB33776
Metabolite Identification
Common NameApiole
DescriptionApiole, also known as apiol or camphre de persil, 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. According to a book called PIHKAL, Apiole had been used to synthesize a psychedelic amphetamine called DMMDA. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation. In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders and as an abortifacient. The name apiole is also used for a closely related compound found in dill and in fennel roots, the positional isomer (dillapiole, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene. Apiole is an extremely weak basic (essentially neutral) compound (based on its pKa). Apiole is a faint and parsley tasting compound. Outside of the human body, Apiole is found, on average, in the highest concentration within parsley. Apiole has also been detected, but not quantified in, several different foods, such as fennels, dills, wild celeries, herbs and spices, and lovages. This could make apiole a potential biomarker for the consumption of these foods. No carcinogenicity was detected with parsley apiol or dill apiol in mice. Hippocrates wrote about parsley as an herb to cause an abortion. It is an irritant and, in high doses, it can cause liver and kidney damage. Plants containing apiole were used by women in the Middle Ages to terminate pregnancies.
Structure
Data?1563862458
Synonyms
ValueSource
1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzeneHMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzeneHMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzeneHMDB
1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzeneHMDB
4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxoleHMDB
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxoleHMDB
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9ciHMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxolHMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxoleHMDB
ApiolHMDB
Apiole (parsley)HMDB
ApiolineHMDB
Camphre de persilHMDB
Parsley apiolHMDB
Parsley apioleHMDB
Parsley camphorHMDB
PetersiliencampherHMDB
Chemical FormulaC12H14O4
Average Molecular Weight222.2372
Monoisotopic Molecular Weight222.089208936
IUPAC Name4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Traditional Nameapiol
CAS Registry Number523-80-8
SMILES
COC1=C2OCOC2=C(OC)C(CC=C)=C1
InChI Identifier
InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3
InChI KeyQQRSPHJOOXUALR-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:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point30 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP2.34ALOGPS
logP2.38ChemAxon
logS-2.6ALOGPS
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
Polarizability22.87 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-2920000000-1cc8f418618578cdd948Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-2a13687cd8d861844f6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2390000000-527ad08f36c5b6d7fc09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-54ca6ec7708d663c0eecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-2497b3799235c68f1f37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-e9c82cedbafb1cfbb38dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aos-3900000000-4c9e9c13ad062d6f79d3Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-5890000000-b5cf6efedda43e9d694cSpectrum
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 IDFDB011929
KNApSAcK IDC00002714
Chemspider ID21106259
KEGG Compound IDC10429
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkApiole
METLIN IDNot Available
PubChem Compound10659
PDB IDNot Available
ChEBI IDNot Available
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.. .