Showing Compound Apiole (FDB011929)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:54 UTC

Update date

2019-11-26 03:05:45 UTC

Primary ID

FDB011929

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Apiole

Description

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.

CAS Number

523-80-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
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
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

Showing 1 to 10 of 23 entries

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H14O4

IUPAC name

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

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

Isomeric SMILES

COC1=C2OCOC2=C(OC)C(CC=C)=C1

Average Molecular Weight

222.2372

Monoisotopic Molecular Weight

222.089208936

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.

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp33 179°	DFC
Charge	Not Available
Density	d204 1.02	DFC
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 64.85%; H 6.35%; O 28.80%	DFC
Melting Point	Mp 30°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00di-5890000000-b5cf6efedda43e9d694c	2015-03-01	View Spectrum
Predicted GC-MS	Apiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-2920000000-1cc8f418618578cdd948	Spectrum
Predicted GC-MS	Apiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Apiole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0190000000-2a13687cd8d861844f6a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2390000000-527ad08f36c5b6d7fc09	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3900000000-54ca6ec7708d663c0eec	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-2497b3799235c68f1f37	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0690000000-e9c82cedbafb1cfbb38d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aos-3900000000-4c9e9c13ad062d6f79d3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-e696c56af8179794e7ad	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-0980000000-013e17a78d3735e96600	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-2900000000-d0e703a0356e829446de	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-b55ce853fd840758bfab	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0290000000-9af70ca3804ef5b209f9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01bc-6940000000-4f291648385a3987c36e	2021-09-24	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33776

CRC / DFC (Dictionary of Food Compounds) ID

HBW16-S:HBW16-S

EAFUS ID

Not Available

Dr. Duke ID

APIOLE|APIOL

BIGG ID

Not Available

KNApSAcK ID

C00002714

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1011001

SuperScent ID

Not Available

Wikipedia ID

Apiole

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
abortifacient	50691	A chemical substance that interrupts pregnancy after implantation.	DUKE
anti dysmenorrheic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti malarial	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti neuralgic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti pyretic	35493	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 reproductive			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
central nervous system stimulant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE
diuretic	35498	An agent that promotes the excretion of urine through its effects on kidney function.	DUKE

Showing 1 to 10 of 20 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
faint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
parsley	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 2 of 2 entries

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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.