U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
3913
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
136
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
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
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
n = 2
Health Status: unhealthy
Condition: anise oil allergy
Age Group: 38 and 39 years
Sex: F
Population Size: 2
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
n = 1
Health Status: unhealthy
Age Group: 63 years
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: 64 years
Sex: F
Population Size: 1
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
n = 15
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 55.1 years
Sex: F
Population Size: 15
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
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
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
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
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
n = 2
Health Status: unhealthy
Condition: anise oil allergy
Age Group: 38 and 39 years
Sex: F
Population Size: 2
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
n = 1
Health Status: unhealthy
Age Group: 63 years
Sex: F
Population Size: 1
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
n = 1
Health Status: healthy
Age Group: 64 years
Sex: F
Population Size: 1
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
n = 15
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 55.1 years
Sex: F
Population Size: 15
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
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
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
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
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
n = 27
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 58 years
Sex: M+F
Population Size: 27
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
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
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
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
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
n = 49
Health Status: unhealthy
Condition: xerostomia
Age Group: mean age 69.1 years
Sex: M+F
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/10487404/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
UGT
29

CYP1A
56

CYP2B
32
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
121
 small
CYP2B
40
 small
UGT
59
 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
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
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
Modulation of thiol homeostasis induced by H2S-releasing aspirin.
2010 May 1
Patents

Patents

20010006699
2
JP2000038328A
2
JP2001163743A
3
JP2007525670A
148
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.
Name Type Language
ANETHOLE, (Z)-
Systematic Name English
ANISOLE, P-PROPENYL-, CIS-
Common Name English
CIS-ANETHOLE
MI  
Systematic 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 Fri Dec 15 17:09:21 GMT 2023 , Edited by admin on Fri Dec 15 17:09:21 GMT 2023
PRIMARY
PUBCHEM
1549040
Created by admin on Fri Dec 15 17:09:21 GMT 2023 , Edited by admin on Fri Dec 15 17:09:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
247-181-4
Created by admin on Fri Dec 15 17:09:21 GMT 2023 , Edited by admin on Fri Dec 15 17:09:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID4058651
Created by admin on Fri Dec 15 17:09:21 GMT 2023 , Edited by admin on Fri Dec 15 17:09:21 GMT 2023
PRIMARY
FDA UNII
78AWK1V4GL
Created by admin on Fri Dec 15 17:09:21 GMT 2023 , Edited by admin on Fri Dec 15 17:09:21 GMT 2023
PRIMARY
MERCK INDEX
m1906
Created by admin on Fri Dec 15 17:09:21 GMT 2023 , Edited by admin on Fri Dec 15 17:09:21 GMT 2023
PRIMARY Merck Index
SUBSTANCE RECORD
Structure of ANETHOLE, (Z)-
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966