ContaminantDB: Apiole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 00:05:40 UTC

Update Date

2016-11-09 01:18:34 UTC

Accession Number

CHEM027929

Identification

Common Name

Apiole

Class

Small Molecule

Description

Apiole 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.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene	HMDB, MeSH
4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole	HMDB, MeSH
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole	HMDB
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxol	HMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxole	HMDB
Apiol	HMDB
Apiole (parsley)	HMDB
Apioline	HMDB
Camphre de persil	HMDB
Parsley apiol	HMDB
Parsley apiole	HMDB
Parsley camphor	HMDB
Petersiliencampher	HMDB

Chemical Formula

C₁₂H₁₄O₄

Average Molecular Mass

222.237 g/mol

Monoisotopic Mass

222.089 g/mol

CAS Registry Number

523-80-8

IUPAC Name

4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

apiol

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 Key

QQRSPHJOOXUALR-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:70353 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.38	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.04 m³·mol⁻¹	ChemAxon
Polarizability	22.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-2920000000-1cc8f418618578cdd948	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-2a13687cd8d861844f6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2390000000-527ad08f36c5b6d7fc09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3900000000-54ca6ec7708d663c0eec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-2497b3799235c68f1f37	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0690000000-e9c82cedbafb1cfbb38d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aos-3900000000-4c9e9c13ad062d6f79d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-e696c56af8179794e7ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-0980000000-013e17a78d3735e96600	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-2900000000-d0e703a0356e829446de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-b55ce853fd840758bfab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0290000000-9af70ca3804ef5b209f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-6940000000-4f291648385a3987c36e	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-5890000000-b5cf6efedda43e9d694c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0033776

FooDB ID

FDB011929

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002714

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Apiole

Chemspider ID

21106259

ChEBI ID

Not Available

PubChem Compound ID

10659

Kegg Compound ID

C10429

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

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.

Apiole (CHEM027929)

Structure for CHEM027929: Apiole