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-
DescriptionSources: http://www.wikidoc.org/index.php/AnetholeCurator'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
Sources: http://www.wikidoc.org/index.php/Anethole
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P08253 Gene ID: 4313.0 Gene Symbol: MMP2 Target Organism: Homo sapiens (Human) |
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Target ID: 4318.0 Gene Symbol: MMP9 |
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Target ID: map04010 |
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Target ID: map04668 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10871845 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21212515 http://www.ncbi.nlm.nih.gov/pubmed/10871845 DOI: 10.1158/0008-5472.SABCS-09-3100 |
Primary | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
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Curative | Unknown Approved UseUnknown |
Doses
Dose | Population | Adverse 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... |
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... |
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... |
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... |
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%) Sources: Diarrhea (grade 1, 11.1%) Flatulence (11.1%) |
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%) Sources: Diarrhea (12.2%) Meteorism (12.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
Contact allergy to toothpaste flavors. | 1978 Aug |
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Effects of the naturally occurring alkenylbenzenes eugenol and trans-anethole on drug-metabolizing enzymes in the rat liver. | 1993 Sep |
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Influence of anethole treatment on the tumour induced by Ehrlich ascites carcinoma cells in paw of Swiss albino mice. | 1995 Aug |
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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 |
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A superior P-H phosphonite: asymmetric allylic substitutions with fenchol-based palladium catalysts. | 2006 Mar 30 |
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Inhibitory effect of anethole on T-lymphocyte proliferation and interleukin-2 production through down-regulation of the NF-AT and AP-1. | 2006 Oct |
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Protective effect of Foeniculum vulgare essential oil and anethole in an experimental model of thrombosis. | 2007 Sep |
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Modulation of thiol homeostasis induced by H2S-releasing aspirin. | 2010 May 1 |
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Anethole exerts antimetatstaic activity via inhibition of matrix metalloproteinase 2/9 and AKT/mitogen-activated kinase/nuclear factor kappa B signaling pathways. | 2011 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.accessdata.fda.gov/scripts/fcn/fcnDetailNavigation.cfm?rpt=eafuslisting&id=125
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10871845
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.
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PRIMARY | Merck Index |
SUBSTANCE RECORD