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Showing Compound Apiole (FDB011929)

Record Information
Version1.0
Creation date2010-04-08 22:09:54 UTC
Update date2019-11-26 03:05:45 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
MOLSDFPDBSMILESInChI
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, 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
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-2.6ALOGPS
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
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-00di-5890000000-b5cf6efedda43e9d694c2015-03-01View Spectrum
Predicted GC-MSApiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-2920000000-1cc8f418618578cdd948Spectrum
Predicted GC-MSApiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSApiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-2a13687cd8d861844f6a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2390000000-527ad08f36c5b6d7fc092016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3900000000-54ca6ec7708d663c0eec2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-2497b3799235c68f1f372016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0690000000-e9c82cedbafb1cfbb38d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aos-3900000000-4c9e9c13ad062d6f79d32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-e696c56af8179794e7ad2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-0980000000-013e17a78d3735e966002021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2900000000-d0e703a0356e829446de2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-b55ce853fd840758bfab2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0290000000-9af70ca3804ef5b209f92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-6940000000-4f291648385a3987c36e2021-09-24View Spectrum
NMR
TypeDescriptionView
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
Food Biomarker OntologyNot Available
VMH 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 An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation.DUKE
Anti dysmenorrheic52217 An agent that alleviates menstrual cramp symptoms, reducing prostaglandin-induced uterine contractions. Therapeutically, it provides relief from dysmenorrhea, commonly used in managing primary dysmenorrhea and other menstrual disorders.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti neuralgic52217 An agent that relieves nerve pain, reducing inflammation and discomfort. It plays a biological role in blocking pain pathways, and has therapeutic applications in managing conditions like trigeminal neuralgia, shingles, and diabetic neuropathy. Key medical uses include treating severe nerve pain, numbness, and tingling sensations.DUKE
Anti pyretic35493 An agent that reduces fever, commonly used to relieve headache, pain, and discomfort associated with elevated body temperature, and to manage fever in various medical conditions, such as infections and inflammatory diseases.DUKE
Anti-reproductiveAn agent that prevents or inhibits the ability of an organism to produce offspring, playing a biological role in population control. Therapeutically, it has applications in contraception and population management. Key medical uses include birth control, sterilization, and treatment of hormone-sensitive cancers, such as prostate cancer.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Central nervous system stimulant35470 An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.DUKE
Diuretic35498 An agent that increases urine production, helping remove excess fluids and salts from the body. It plays a key biological role in regulating fluid balance and blood pressure. Therapeutically, diuretics are used to treat conditions such as hypertension, edema, and heart failure, helping reduce swelling and lower blood pressure.DUKE
EmmenagogueAn agent that stimulates blood flow in the pelvic area and uterus, often used to induce or regulate menstruation, treating conditions like amenorrhea and dysmenorrhea.DUKE
Hepatotoxic50908 An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Intoxicant52209 A substance that alters mental and physical function, often producing feelings of euphoria. Its biological role involves disrupting normal brain chemistry. Therapeutically, intoxicants have limited applications, but some are used to manage anxiety, insomnia, or pain. Key medical uses include anesthetics, sedatives, and pain relievers, although their potential for abuse and addiction is high.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
SecretolyticAn agent that increases serous mucus production in the respiratory tract, aiding in clearing debris and excess mucus. Its therapeutic applications include relieving respiratory congestion and coughs, making it useful in managing conditions like bronchitis, asthma, and chronic obstructive pulmonary disease (COPD).DUKE
SynergistA substance or agent that enhances the effect of another, creating a greater overall impact. Biologically, it amplifies cellular responses. Therapeutically, synergists are used to increase drug efficacy, reduce dosages, and minimize side effects. Key medical uses include combination therapies for cancer, infectious diseases, and pain management, where synergists can improve treatment outcomes and patient responses.DUKE
Utero tonic52217 An agent that stimulates and strengthens the uterine muscles, aiding in childbirth and reducing postpartum bleeding. Therapeutically, it is used to induce labor, manage uterine atony, and treat menstrual disorders, promoting overall reproductive health.DUKE
Vasodilator35620 An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.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.