ANETHOLE, (Z)-

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

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

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
72 kDa type IV collagenase 5	Inhibitor 8,297
matrix metallopeptidase 9 2	Inhibitor 8,297
MAPK signaling pathway 26	Inhibitor 8,297
TNF signaling pathway 4	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592	Primary	Basic research	Unknown
Inflammation 102	Curative	Basic research	Unknown
Salmonellosis 5	Curative	Basic research	Unknown

Doses

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Dose	Population	Adverse events
5 % 1 times / day single, topical Studied dose	unhealthy, 38 and 39 years	Other AEs: Contact dermatitis...
2 % 1 times / day single, topical Studied dose	unhealthy, 63 years	Other AEs: Cheilitis...
5 % 1 times / day single, topical Studied dose	healthy, 64 years	Other AEs: Allergic contact dermatitis...
25 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 55.1 years	Other AEs: Flatulence...
25 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 58 years	Other AEs: Gastrointestinal upset, Diarrhea...

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AEs

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AE	Significance	Dose	Population
Contact dermatitis		5 % 1 times / day single, topical Studied dose	unhealthy, 38 and 39 years
Cheilitis		2 % 1 times / day single, topical Studied dose	unhealthy, 63 years
Allergic contact dermatitis		5 % 1 times / day single, topical Studied dose	healthy, 64 years
Flatulence	100%	25 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 55.1 years
Flatulence	11.1%	25 mg 3 times / day multiple, oral Recommended	unhealthy, mean age 58 years

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		UGT 29 CYP1A 56 CYP2B 32

Drug as perpetrator

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Target	Modality	Activity
CYP1A 121	inducer 1,573	small
CYP2B 40	inducer 1,573	small
UGT 59	inducer 1,573	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Cardiovascular effects of the essential oil of Croton zehntneri leaves and its main constituents, anethole and estragole, in normotensive conscious rats.	2006 Apr 11	16325210
Inhibitory effect of anethole on T-lymphocyte proliferation and interleukin-2 production through down-regulation of the NF-AT and AP-1.	2006 Oct	16531003

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Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Anethole at concentration 1mM is a potent inhibitor of TNF-induced NF-kappaB activation, IkappaBalpha phosphorylation and degradation, and NF-kappaB reporter gene expression.

Show entries

Name

Type

Language

ANETHOLE, (Z)-

Systematic Name

English

ANISOLE, P-PROPENYL-, CIS-

Common Name

English

CIS-ANETHOLE

Systematic Name

English

ANETHOLE, CIS

Common Name

English

BENZENE, 1-METHOXY-4-(1-PROPENYL)-, (Z)-

Common Name

English

Showing 1 to 5 of 8 entries

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Code System

Code

Type

Description

CAS

25679-28-1

PRIMARY

PUBCHEM

1549040

PRIMARY

ECHA (EC/EINECS)

247-181-4

PRIMARY

EPA CompTox

DTXSID4058651

PRIMARY

FDA UNII

78AWK1V4GL

PRIMARY

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SUBSTANCE RECORD


					78AWK1V4GL

ANETHOLE, (Z)-

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

Drug as perpetrator