trans-Anethole

• CAS: 4180-23-8
• Catalog Number: ACM4180238
• Category: Alkenes
• Molecular Weight: 148.20
• Molecular Formula: C10H12O
• Melting Point: 23°C
• Flash Point: 90°C
• Density: 0.9875
• Solubility: water, 98.68 mg/L @ 25 °C (est)
• Appearance: Colorless to faint yellow liquid or white crystalline solid
• Assay: 0.99
• EC Number: 224-052-0
• Hazard Statements: H302-H315
• MDL Number: MFCD00009284
• Packaging: 1 kg
• Refractive Index: 1.559-1.562
• RIDADR: UN 3295C 3 / PGIII
• Stability: Stable under normal temperatures and pressures.
• Storage Conditions: 2-8°C
• Symbol: GHS07

Case Study

Trans-Anethole as a Bioactive Agent for Medicinal and Cosmetic Applications

Sharafan, Marta, et al. Molecules 27.3 (2022): 650.

Trans-anethole, the dominant phenylpropanoid of star anise essential oil, functions as a multifunctional bioactive agent whose antimicrobial, anti-inflammatory, antioxidant and anti-obesity activities underpin medicinal and cosmetic use.
Experimental Protocol: Essential oil is recovered from Illicium verum fruit by steam distillation, solvent extraction or supercritical fluid extraction, and trans-anethole content is quantified by gas chromatography-mass spectrometry. Antibacterial susceptibility is assessed by minimum inhibitory concentration assays against drug-resistant bacteria, while antifungal activity is screened against eleven plant-pathogenic fungal strains. Anti-inflammatory efficacy is evaluated in mice with elastase- and lipopolysaccharide-induced pulmonary disease after oral administration at four doses ranging from 62.5 to 500 mg/kg, and anti-obesity effects are examined in high-fat-diet-fed mice.
Performance Evaluation: Trans-anethole constitutes 72-92% of the essential oil, with extraction-dependent contents of 70.61-77.31%. It inhibits Acinetobacter baumannii with a minimum inhibitory concentration below 0.1 mg/mL and suppresses fungal growth with IC50 values of 0.06-0.25 mg/mL. Oral dosing lowers the pro-inflammatory cytokines IL-6 and TNF-alpha, and the compound induces browning of white adipocytes with increased UCP1 and related markers. These data support trans-anethole as a safe raw material for perfumery, anti-aging cosmetics and dietary supplements.

Trans-Anethole as a Key Odorant for Structure-Odor Relationship Studies

Hasegawa, Toshio, et al. Natural Product Communications 9.2 (2014): 1934578X1400900230.

Trans-anethole serves as the key odorant defining the anise-like aroma of star anise, and systematic modification of its methoxy and 1-propenyl substituents reveals how molecular structure governs odor expression in fragrance chemistry.
Experimental Protocol: Star anise odorants are extracted by steam distillation, n-hexane extraction and monolithic material sorptive extraction, with component identification by gas chromatography-olfactometry and gas chromatography-mass spectrometry. Anethole derivatives are synthesized, for example by refluxing 1-(4-methoxyphenyl)-1-propanol with 4.8 N hydrochloric acid in acetone for 90 min, and the purified products are assessed by both an expert panel and a group of untrained participants, whose odor evaluations are consistent.
Performance Evaluation: (E)-Anethole accounts for 76.2% of the n-hexane extract and p-anisaldehyde for 12.3%, the two compounds together representing 88.5% of the extract. Synthesized (E)-anethole is obtained in 78% yield with an E/Z ratio of 97/3 and shows a strong anise-like odor. Derivatives in which the methoxy group is replaced by hydrogen lose the characteristic odor and instead display fatty notes, while Z-isomers show sour, fresh and fruity characteristics, demonstrating that the methoxy benzene moiety and double-bond geometry are essential for the aroma of star anise.

Custom Q&A

What is the molecular formula of trans-Anethole?

The molecular formula of trans-Anethole is C10H12O.

What is the molecular weight of trans-Anethole?

The molecular weight of trans-Anethole is 148.20 g/mol.

What are some synonyms for trans-Anethole?

Some synonyms for trans-Anethole include ANETHOLE and (E)-Anethole.

What is the IUPAC name of trans-Anethole?

The IUPAC name of trans-Anethole is 1-methoxy-4-[(E)-prop-1-enyl]benzene.

What is the InChIKey of trans-Anethole?

The InChIKey of trans-Anethole is RUVINXPYWBROJD-ONEGZZNKSA-N.

What is the canonical SMILES of trans-Anethole?

The canonical SMILES of trans-Anethole is CC=CC1=CC=C(C=C1)OC.

What is the CAS number of trans-Anethole?

The CAS number of trans-Anethole is 104-46-1.

What is the FEMA number of trans-Anethole?

The FEMA number of trans-Anethole is 2086.

What is the UNII of trans-Anethole?

The UNII of trans-Anethole is Q3JEK5DO4K.

Where is trans-Anethole found in nature?

trans-Anethole is a natural product found in Erucaria microcarpa, Anemopsis californica, and other organisms.