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-ONEGZZNKSA-N
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
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 |
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 |
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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 |
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Sensitizing and irritating properties of star anise oil. | 1976 Dec |
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Contact allergy to toothpaste flavors. | 1978 Aug |
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Histopathological evaluation of proliferative liver lesions in rats fed trans-anethole in chronic studies. | 1989 Jan |
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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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Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. | 2003 Jul 1 |
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Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors. | 2004 Dec |
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Molecular and pharmacological analysis of an octopamine receptor from American cockroach and fruit fly in response to plant essential oils. | 2005 Jul |
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Synthesis and antioxidant, anti-inflammatory and gastroprotector activities of anethole and related compounds. | 2005 Jul 1 |
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Cardiovascular effects of the essential oil of Croton zehntneri leaves and its main constituents, anethole and estragole, in normotensive conscious rats. | 2006 Apr 11 |
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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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:20:38 GMT 2023
by
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on
Fri Dec 15 15:20:38 GMT 2023
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Record UNII |
Q3JEK5DO4K
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION |
SCCS/1459/11
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NCI_THESAURUS |
C737
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JECFA EVALUATION |
TRANS-ANETHOLE
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100000077400
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C76862
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17881
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ANETHOLE
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637563
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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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.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Pure compound identified in the P. lactiflora root steam distillate.
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Related Record | Type | Details | ||
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METABOLITE TOXIC -> PARENT |
IN-VIVO
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |