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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O
Molecular Weight 148.2017
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ANETHOLE, (Z)-

SMILES

COC1=CC=C(\C=C/C)C=C1

InChI

InChIKey=RUVINXPYWBROJD-ARJAWSKDSA-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 148.2017
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

CNS Active
4002
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

Cahours, A.
2
Sources: DOI: 10.1002/jlac.18420410107

Approval Year

1993
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
72 kDa type IV collagenase
5
Target ID: P08253
Gene ID: 4313.0
Gene Symbol: MMP2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
Curative
Basic research
Unknown

Approved Use

Unknown
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:
https://pubmed.ncbi.nlm.nih.gov/9255488/
unhealthy, 38 and 39 years
Health Status: unhealthy
Age Group: 38 and 39 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9255488/
Other AEs: Contact dermatitis...
Other AEs:
Contact dermatitis
Sources:
https://pubmed.ncbi.nlm.nih.gov/9255488/
2 % 1 times / day single, topical
Studied dose
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17034478/
unhealthy, 63 years
Health Status: unhealthy
Age Group: 63 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17034478/
Other AEs: Cheilitis...
Other AEs:
Cheilitis
Sources:
https://pubmed.ncbi.nlm.nih.gov/17034478/
5 % 1 times / day single, topical
Studied dose
Dose: 5 %, 1 times / day
Route: topical
Route: single
Dose: 5 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9687050/
healthy, 64 years
Health Status: healthy
Age Group: 64 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9687050/
Other AEs: Allergic contact dermatitis...
Other AEs:
Allergic contact dermatitis
Sources:
https://pubmed.ncbi.nlm.nih.gov/9687050/
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:
https://pubmed.ncbi.nlm.nih.gov/3291100/
unhealthy, mean age 55.1 years
Health Status: unhealthy
Age Group: mean age 55.1 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3291100/
Other AEs: Flatulence...
Other AEs:
Flatulence (100%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3291100/
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:
https://pubmed.ncbi.nlm.nih.gov/6358997/
unhealthy, mean age 58 years
Health Status: unhealthy
Age Group: mean age 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6358997/
Other AEs: Gastrointestinal upset, Diarrhea...
Other AEs:
Gastrointestinal upset (grade 1, 11.1%)
Diarrhea (grade 1, 11.1%)
Flatulence (11.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6358997/
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:
https://pubmed.ncbi.nlm.nih.gov/10487404/
unhealthy, mean age 69.1 years
Health Status: unhealthy
Age Group: mean age 69.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10487404/
Other AEs: Taste abnormality, Diarrhea...
Other AEs:
Taste abnormality (12.2%)
Diarrhea (12.2%)
Meteorism (12.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10487404/
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:
https://pubmed.ncbi.nlm.nih.gov/9255488/
unhealthy, 38 and 39 years
Health Status: unhealthy
Age Group: 38 and 39 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9255488/
Cheilitis
2 % 1 times / day single, topical
Studied dose
Dose: 2 %, 1 times / day
Route: topical
Route: single
Dose: 2 %, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17034478/
unhealthy, 63 years
Health Status: unhealthy
Age Group: 63 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17034478/
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:
https://pubmed.ncbi.nlm.nih.gov/9687050/
healthy, 64 years
Health Status: healthy
Age Group: 64 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/9687050/
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:
https://pubmed.ncbi.nlm.nih.gov/3291100/
unhealthy, mean age 55.1 years
Health Status: unhealthy
Age Group: mean age 55.1 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/3291100/
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:
https://pubmed.ncbi.nlm.nih.gov/6358997/
unhealthy, mean age 58 years
Health Status: unhealthy
Age Group: mean age 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6358997/
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:
https://pubmed.ncbi.nlm.nih.gov/6358997/
unhealthy, mean age 58 years
Health Status: unhealthy
Age Group: mean age 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6358997/
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:
https://pubmed.ncbi.nlm.nih.gov/6358997/
unhealthy, mean age 58 years
Health Status: unhealthy
Age Group: mean age 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/6358997/
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:
https://pubmed.ncbi.nlm.nih.gov/10487404/
unhealthy, mean age 69.1 years
Health Status: unhealthy
Age Group: mean age 69.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10487404/
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:
https://pubmed.ncbi.nlm.nih.gov/10487404/
unhealthy, mean age 69.1 years
Health Status: unhealthy
Age Group: mean age 69.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10487404/
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:
https://pubmed.ncbi.nlm.nih.gov/10487404/
unhealthy, mean age 69.1 years
Health Status: unhealthy
Age Group: mean age 69.1 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/10487404/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
UGT
32

CYP1A
59

CYP2B
32
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
122
 small
CYP2B
41
 small
UGT
70
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:2716
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2716
MolPort
MolPort-004-288-385
https://www.molport.com/shop/molecule-link/MolPort-004-288-385
PubMed

PubMed

TitleDatePubMed
Anethole exerts antimetatstaic activity via inhibition of matrix metalloproteinase 2/9 and AKT/mitogen-activated kinase/nuclear factor kappa B signaling pathways.
2011
Modulation of thiol homeostasis induced by H2S-releasing aspirin.
2010-05-01
Protective effect of Foeniculum vulgare essential oil and anethole in an experimental model of thrombosis.
2007-09
Inhibitory effect of anethole on T-lymphocyte proliferation and interleukin-2 production through down-regulation of the NF-AT and AP-1.
2006-10
Cardiovascular effects of the essential oil of Croton zehntneri leaves and its main constituents, anethole and estragole, in normotensive conscious rats.
2006-04-11
A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts.
2006-03-30
Synthesis and antioxidant, anti-inflammatory and gastroprotector activities of anethole and related compounds.
2005-07-01
Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils.
2005-07
Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors.
2004-12
Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells.
2003-07-01
Anethole blocks both early and late cellular responses transduced by tumor necrosis factor: effect on NF-kappaB, AP-1, JNK, MAPKK and apoptosis.
2000-06-08
Influence of anethole treatment on the tumour induced by Ehrlich ascites carcinoma cells in paw of Swiss albino mice.
1995-08
Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver.
1993-09
Histopathological evaluation of proliferative liver lesions in rats fed trans-anethole in chronic studies.
1989-01
Contact allergy to toothpaste flavors.
1978-08
Sensitizing and irritating properties of star anise oil.
1976-12
Patents

Patents

20010006699
2
JP2000038328A
2
JP2001163743A
3
JP2007525670A
150
JPH01294601A
8
JPH05155744A
5
JPH0624952A
2
JPH07242505A
2
JPH0812541A
3
JPH1112145A
2
JPH11152217A
3
JPH11255629A
2
JPH11318948A
2
JPS58162520A
2
JPS601118A
2
JPS60130509A
2
JPS62155207A
3

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 Mon Mar 31 18:41:10 GMT 2025
Edited
by admin
on Mon Mar 31 18:41:10 GMT 2025
Record UNII
78AWK1V4GL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIS-ANETHOLE
MI  
Preferred Name English
ANETHOLE, (Z)-
Systematic Name English
ANISOLE, P-PROPENYL-, CIS-
Common Name English
ANETHOLE, CIS
Common Name English
BENZENE, 1-METHOXY-4-(1-PROPENYL)-, (Z)-
Common Name English
CIS-ANETHOLE [MI]
Common Name English
ANETHOLE, CIS-
Systematic Name English
(Z)-ANETHOLE
Systematic Name English
Code System Code Type Description
CAS
25679-28-1
Created by admin on Mon Mar 31 18:41:10 GMT 2025 , Edited by admin on Mon Mar 31 18:41:10 GMT 2025
PRIMARY
PUBCHEM
1549040
Created by admin on Mon Mar 31 18:41:10 GMT 2025 , Edited by admin on Mon Mar 31 18:41:10 GMT 2025
PRIMARY
ECHA (EC/EINECS)
247-181-4
Created by admin on Mon Mar 31 18:41:10 GMT 2025 , Edited by admin on Mon Mar 31 18:41:10 GMT 2025
PRIMARY
EPA CompTox
DTXSID4058651
Created by admin on Mon Mar 31 18:41:10 GMT 2025 , Edited by admin on Mon Mar 31 18:41:10 GMT 2025
PRIMARY
FDA UNII
78AWK1V4GL
Created by admin on Mon Mar 31 18:41:10 GMT 2025 , Edited by admin on Mon Mar 31 18:41:10 GMT 2025
PRIMARY
MERCK INDEX
m1906
Created by admin on Mon Mar 31 18:41:10 GMT 2025 , Edited by admin on Mon Mar 31 18:41:10 GMT 2025
PRIMARY Merck Index
Related Record Type Details
FOENICULUM VULGARE FRUIT OIL
PARENT -> CONSTITUENT MAY BE PRESENT
ANISE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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