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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

SMILES

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

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 148.2017
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
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
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
Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors.
2004 Dec
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

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:38 GMT 2023
Record UNII
Q3JEK5DO4K
Record Status Validated (UNII)
Record Version
  • Download
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, (E)-
Systematic Name English
BENZENE, 1-METHOXY-4-(1-PROPENYL)-, (E)-
Common Name English
Anethole [WHO-DD]
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 Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
JECFA EVALUATION TRANS-ANETHOLE
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
Code System Code Type Description
NSC
209529
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
SMS_ID
100000077400
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
NCI_THESAURUS
C76862
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
RS_ITEM_NUM
1035005
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
RXCUI
17881
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL452630
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
EVMPD
SUB12901MIG
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
224-052-0
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
WIKIPEDIA
ANETHOLE
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
CAS
4180-23-8
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
FDA UNII
Q3JEK5DO4K
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
MESH
C006578
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
CHEBI
35616
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
DAILYMED
Q3JEK5DO4K
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
JECFA MONOGRAPH
192
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
MERCK INDEX
m1906
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY Merck Index
PUBCHEM
637563
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020087
Created by admin on Fri Dec 15 15:20:38 GMT 2023 , Edited by admin on Fri Dec 15 15:20:38 GMT 2023
PRIMARY
Related Record Type Details
FENNEL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
ELYMUS REPENS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 6.80% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
MYRRH
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
ANISE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (GC)
ANISE
PARENT -> CONSTITUENT ALWAYS PRESENT
PAEONIA LACTIFLORA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Pure compound identified in the P. lactiflora root steam distillate.
Related Record Type Details
Structure of ANETHOLE OXIDE, TRANS-
METABOLITE TOXIC -> PARENT
IN-VIVO
URINE
Related Record Type Details
Structure of ANETHOLE
ACTIVE MOIETY
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