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Record Information
Version5.0
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 is found in dill. Apiole occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. 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. It is an irritant and in high doses it is toxic and can cause liver and kidney damage.
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, MeSH
4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxoleHMDB, MeSH
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 Molecular Properties
PropertyValueReference
Melting Point30 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
AllCCS[M+H]+ExperimentalNot Available146.083http://allccs.zhulab.cn/database/detail?ID=AllCCS00001126
DarkChem[M+H]+PredictedNot Available152.01431661259
DarkChem[M-H]-PredictedNot Available147.42931661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-2920000000-1cc8f418618578cdd9482017-09-01View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00di-5890000000-b5cf6efedda43e9d694c2015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-2a13687cd8d861844f6a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2390000000-527ad08f36c5b6d7fc092016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-54ca6ec7708d663c0eec2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-2497b3799235c68f1f372016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-e9c82cedbafb1cfbb38d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aos-3900000000-4c9e9c13ad062d6f79d32016-08-03View 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 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 IDNot Available
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.. .