Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2015-07-20 22:44:50 UTC
Primary IDFDB011929
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameApiole
DescriptionOccurs 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.
CAS Number523-80-8
Structure
Thumb
Synonyms
SynonymSource
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
1,3-Benzodioxole, 4, 7-dimethoxy-5-(2-propenyl)-biospider
1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-biospider
1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-biospider
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9CIdb_source
Benzene, 1-allyl-2,5-dimethoxy-3, 4-(methylenedioxy)-biospider
Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP2.34ALOGPS
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
Polarizability22.87 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H14O4
IUPAC name4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C2OCOC2=C(OC)C(CC=C)=C1
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
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 30°DFC
Boiling PointBp33 179°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 280 () (no solvent reported)DFC
Densityd204 1.02DFC
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-2920000000-1cc8f418618578cdd948View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-2a13687cd8d861844f6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2390000000-527ad08f36c5b6d7fc09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-54ca6ec7708d663c0eecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-2497b3799235c68f1f37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-e9c82cedbafb1cfbb38dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aos-3900000000-4c9e9c13ad062d6f79d3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-5890000000-b5cf6efedda43e9d694cView in MoNA
ChemSpider ID21106259
ChEMBL IDCHEMBL1560118
KEGG Compound IDC10429
Pubchem Compound ID10659
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33776
CRC / DFC (Dictionary of Food Compounds) IDHBW16-S:HBW16-S
EAFUS IDNot Available
Dr. Duke IDAPIOLE|APIOL
BIGG IDNot Available
KNApSAcK IDC00002714
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1011001
SuperScent IDNot Available
Wikipedia IDApiole
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
abortifacient50691 A chemical substance that interrupts pregnancy after implantation.DUKE
anti dysmenorrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti reproductiveDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
emmenagogueDUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.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
intoxicant52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
irritantDUKE
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
secretolyticDUKE
synergistDUKE
utero tonic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
vasodilator35620 A drug used to cause dilation of the blood vessels.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
parsley
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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.