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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O
Molecular Weight 148.2021
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ANETHOLE

SMILES

C/C(/[H])=C(\[H])/c1ccc(cc1)OC

InChI

InChIKey=RUVINXPYWBROJD-ONEGZZNKSA-N
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+

HIDE SMILES / InChI

Molecular Formula C10H12O
Molecular Weight 148.2021
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including: http://www.drugfuture.com/chemdata/ANETHOLE.html http://www4.mpbio.com/ecom/docs/proddata.nsf/(webtds2)/150378

Anethole is a flavoring agent in foods and beverages; in perfumery, particularly for soap and dentifrices. The more abundant isomer, and the one preferred for use, is the trans- or E isomer. It is distinctly sweet, measuring 13 times sweeter than sugar. Anethole has potent antimicrobial properties, against bacteria, yeast, and fungi. Anethole also has nematicidal activity and is a promising insecticide. Several essential oils consisting mostly of anethole have insecticidal action. Anethole has estrogenic activity. It is slightly toxic and may act as an irritant in large quantities.

CNS Activity

Curator's Comment:: After intravenous dosing in mice, most of the anethole accumulated in the liver, lung and brain. Anethole is largely used as a substrate for the synthesis of various substances of neuro-pharmaceutical interest such as chloral, an anticonvulsant, and amphetamine.

Originator

Sources: DOI: 10.1002/jlac.18420410107

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08253
Gene ID: 4313.0
Gene Symbol: MMP2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

Doses

Doses

DosePopulationAdverse events​
5 % 1 times / day single, topical
Studied dose
Dose: 5 %, 1 times / day
Route: topical
Route: single
Dose: 5 %, 1 times / day
Sources:
unhealthy, 38 and 39 years
n = 2
Health Status: unhealthy
Condition: anise oil allergy
Age Group: 38 and 39 years
Sex: F
Population Size: 2
Sources:
Other AEs: Contact dermatitis...
Other AEs:
Contact dermatitis
Sources:
2 % 1 times / day single, topical
Studied dose
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
unhealthy, 63 years
n = 1
Health Status: unhealthy
Age Group: 63 years
Sex: F
Population Size: 1
Sources:
Other AEs: Cheilitis...
Other AEs:
Cheilitis
Sources:
5 % 1 times / day single, topical
Studied dose
Dose: 5 %, 1 times / day
Route: topical
Route: single
Dose: 5 %, 1 times / day
Sources:
healthy, 64 years
n = 1
Health Status: healthy
Age Group: 64 years
Sex: F
Population Size: 1
Sources:
Other AEs: Allergic contact dermatitis...
Other AEs:
Allergic contact dermatitis
Sources:
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy, mean age 55.1 years
n = 15
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 55.1 years
Sex: F
Population Size: 15
Sources:
Other AEs: Flatulence...
Other AEs:
Flatulence (100%)
Sources:
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy, mean age 58 years
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
Sources:
Other AEs: Gastrointestinal upset, Diarrhea...
Other AEs:
Gastrointestinal upset (grade 1, 11.1%)
Diarrhea (grade 1, 11.1%)
Flatulence (11.1%)
Sources:
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, mean age 69.1 years
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
Sources:
Other AEs: Taste abnormality, Diarrhea...
Other AEs:
Taste abnormality (12.2%)
Diarrhea (12.2%)
Meteorism (12.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Contact dermatitis
5 % 1 times / day single, topical
Studied dose
Dose: 5 %, 1 times / day
Route: topical
Route: single
Dose: 5 %, 1 times / day
Sources:
unhealthy, 38 and 39 years
n = 2
Health Status: unhealthy
Condition: anise oil allergy
Age Group: 38 and 39 years
Sex: F
Population Size: 2
Sources:
Cheilitis
2 % 1 times / day single, topical
Studied dose
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
unhealthy, 63 years
n = 1
Health Status: unhealthy
Age Group: 63 years
Sex: F
Population Size: 1
Sources:
Allergic contact dermatitis
5 % 1 times / day single, topical
Studied dose
Dose: 5 %, 1 times / day
Route: topical
Route: single
Dose: 5 %, 1 times / day
Sources:
healthy, 64 years
n = 1
Health Status: healthy
Age Group: 64 years
Sex: F
Population Size: 1
Sources:
Flatulence 100%
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy, mean age 55.1 years
n = 15
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 55.1 years
Sex: F
Population Size: 15
Sources:
Flatulence 11.1%
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy, mean age 58 years
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
Sources:
Diarrhea grade 1, 11.1%
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy, mean age 58 years
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
Sources:
Gastrointestinal upset grade 1, 11.1%
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
unhealthy, mean age 58 years
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
Sources:
Diarrhea 12.2%
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, mean age 69.1 years
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
Sources:
Meteorism 12.2%
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, mean age 69.1 years
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
Sources:
Taste abnormality 12.2%
50 mg 3 times / day multiple, oral
Studied dose
Dose: 50 mg, 3 times / day
Route: oral
Route: multiple
Dose: 50 mg, 3 times / day
Sources:
unhealthy, mean age 69.1 years
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Sensitizing and irritating properties of star anise oil.
1976 Dec
Contact allergy to toothpaste flavors.
1978 Aug
Histopathological evaluation of proliferative liver lesions in rats fed trans-anethole in chronic studies.
1989 Jan
Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver.
1993 Sep
Influence of anethole treatment on the tumour induced by Ehrlich ascites carcinoma cells in paw of Swiss albino mice.
1995 Aug
Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kappaB, AP-1, JNK, MAPKK and apoptosis.
2000 Jun 8
Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells.
2003 Jul 1
Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors.
2004 Dec
Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils.
2005 Jul
Synthesis and antioxidant, anti-inflammatory and gastroprotector activities of anethole and related compounds.
2005 Jul 1
Cardiovascular effects of the essential oil of Croton zehntneri leaves and its main constituents, anethole and estragole, in normotensive conscious rats.
2006 Apr 11
A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts.
2006 Mar 30
Inhibitory effect of anethole on T-lymphocyte proliferation and interleukin-2 production through down-regulation of the NF-AT and AP-1.
2006 Oct
Protective effect of Foeniculum vulgare essential oil and anethole in an experimental model of thrombosis.
2007 Sep
Modulation of thiol homeostasis induced by H2S-releasing aspirin.
2010 May 1
Anethole exerts antimetatstaic activity via inhibition of matrix metalloproteinase 2/9 and AKT/mitogen-activated kinase/nuclear factor kappa B signaling pathways.
2011
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Trans-anethol is one of the substances directly added to food by the U.S. Food and Drug Administration (FDA).
Unknown
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: Aanethol's MIC(50) for bacterias vary from 3 to 45 ug/ml for fungus from 5 to 50 ug/ml. http://www.ncbi.nlm.nih.gov/pubmed/11807977
Anethole at concentration 1mM is a potent inhibitor of TNF-induced NF-kappaB activation, IkappaBalpha phosphorylation and degradation, and NF-kappaB reporter gene expression.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:49:15 UTC 2021
Edited
by admin
on Sat Jun 26 03:49:15 UTC 2021
Record UNII
Q3JEK5DO4K
Record Status Validated (UNII)
Record Version
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Name Type Language
ANETHOLE
FCC   II   INCI   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
ANETHOLE (NATURAL)
Common Name English
(E)-ANETHOLE
Systematic Name English
ANETHOLE [WHO-DD]
Common Name English
ANETHOLE, (E)-
Systematic Name English
BENZENE, 1-METHOXY-4-(1-PROPENYL)-, (E)-
Common Name English
MONASIRUP
Brand Name English
ANETHOLE [MI]
Common Name English
ANETHOLE [II]
Common Name English
ANETHOLE, TRANS-
Systematic Name English
NSC-209529
Code English
ANETHOLE [VANDF]
Common Name English
TRANS-ANETHOLE
FHFI  
Systematic Name English
ANETHOLE [FCC]
Common Name English
TRANS-1-P-ANISYLPROPENE
Common Name English
TRANS-ANETHOLE [FHFI]
Common Name English
ANETHOLE [INCI]
Common Name English
1-METHOXY-4-(1E)-1-PROPEN-1-YLBENZENE
Systematic Name English
TRANS-P-PROPENYLANISOLE
Common Name English
FEMA NO. 2086
Code English
(E)-ANETHOLE (CONSTITUENT OF MYRRH) [DSC]
Common Name English
ISOESTRAGOLE
Common Name English
ANETHOLE [USP-RS]
Common Name English
(E)-P-PROPENYLANISOLE
Common Name English
ANISE CAMPHOR
Common Name English
ANETHOLE, TRANS
Common Name English
Classification Tree Code System Code
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
NCI_THESAURUS C737
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
JECFA EVALUATION TRANS-ANETHOLE
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C76862
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
RXCUI
17881
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL452630
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
EVMPD
SUB12901MIG
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
ECHA (EC/EINECS)
224-052-0
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
WIKIPEDIA
ANETHOLE
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
CAS
4180-23-8
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
FDA UNII
Q3JEK5DO4K
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
MESH
C006578
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
USP_CATALOG
1035005
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M1906
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY Merck Index
PUBCHEM
637563
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
EPA CompTox
4180-23-8
Created by admin on Sat Jun 26 03:49:15 UTC 2021 , Edited by admin on Sat Jun 26 03:49:15 UTC 2021
PRIMARY
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