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W208604

Sigma-Aldrich

trans-Anethole

≥99%, FCC, FG

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Synonym(s):
4-Propenylanisole, trans-1-Methoxy-4-(1-propenyl)benzene
Linear Formula:
CH3CH=CHC6H4OCH3
CAS Number:
4180-23-8
Molecular Weight:
148.20
FEMA Number:
2086
Beilstein:
774229
EC Number:
224-052-0
Council of Europe no.:
183
MDL number:
MFCD00009284
UNSPSC Code:
12164502
PubChem Substance ID:
24900856
Flavis number:
4.010
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines
meets purity specifications of JECFA

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
FCC
FDA 21 CFR 117
FDA 21 CFR 182.60

Assay

≥99%

form

liquid

refractive index

n20/D 1.561 (lit.)

bp

234-237 °C (lit.)

mp

20-21 °C (lit.)

density

0.988 g/mL at 25 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

trans-anethole

Organoleptic

anise; sweet

SMILES string

COc1ccc(\C=C\C)cc1

InChI

1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+

InChI key

RUVINXPYWBROJD-ONEGZZNKSA-N

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Application


  • Anti-oral streptococci and anti-biofilm properties of Etlingera pavieana essential oil and its bioactive compounds proposed for an alternative herbal mouthwash.: This study evaluates the antimicrobial properties of Etlingera pavieana essential oil, identifying trans-anethole as a key bioactive compound with potential applications in oral hygiene products (Wongsariya et al., 2024).

  • Efficacy and safety of aniseed powder for treating gastrointestinal symptoms of COVID-19: a randomized, placebo-controlled trial.: The trial highlights the therapeutic potential of aniseed powder, rich in trans-anethole, for alleviating gastrointestinal symptoms in COVID-19 patients (Mosaffa-Jahromi et al., 2024).

  • Transcriptomic and biochemical analyses revealed antifungal mechanism of trans-anethole on Aspergillus flavus growth.: This research elucidates the antifungal mechanism of trans-anethole against Aspergillus flavus, suggesting its potential application in controlling fungal contamination in food and agriculture (Lei et al., 2023).

Biochem/physiol Actions

Naturally occurring phenylpropene derivative that is estrogenic at lower concentrations and cytotoxic at higher concentrations to cancer cell lines. The cytotoxicity is related to the metabolism of trans-anethole to 4-hydroxy-1-propenylbenzene.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Eun Jeong Choo et al.
Biological & pharmaceutical bulletin, 34(1), 41-46 (2011-01-08)
Anethole is known to possess anti-inflammatory and anti-tumor activities and to be a main constituent of fennel, anise, and camphor. In the present study, we evaluated anti-metastatic and apoptotic effects of anethole on highly-metastatic HT-1080 human fibrosarcoma tumor cells. Despite
Rajesh K Joshi et al.
Natural product communications, 6(1), 141-143 (2011-03-04)
The essential oil of the leaves of Feronia elephantum Corr. was analyzed by gas chromatography and gas chromatography/mass spectrometry. The main constituents were beta-pinene (28.4%), Z-anethole (22.1%), methyl chavicol (12.0%) and E-anethole (8.1%), among thirty-three identified compounds, which represented 92.6%
Bülent Cetin et al.
Journal of medicinal food, 13(1), 196-204 (2010-02-09)
The objective of this study was to determine the chemical compositions of the essential oil and hexane extract isolated from the inflorescence, leaf stems, and aerial parts of Florence fennel and the antimicrobial activities of the essential oil, hexane extract
Meher U Nessa et al.
Anticancer research, 32(11), 4843-4850 (2012-11-17)
Chemopreventative phytochemicals having antitumour and antioxidant properties can overcome problems of chemoresistance and nonspecific toxicity towards normal cells that are associated with platinum-based chemotherapy against cancer. These agents exert their effects by bringing into play numerous cellular proteins that in
Hong-Ik Cho et al.
Journal of natural products, 76(9), 1717-1723 (2013-08-22)
The aim of this study was to investigate the hepatoprotective effect of anethole (trans-anethole, 1), a major component of Foeniculum vulgare, and its molecular mechanism during ischemia/reperfusion (I/R). Mice were subjected to 60 min of partial hepatic ischemia followed by
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