(Z)-anethole

• CAS: 25679-28-1
• Catalog Number: ACM25679281
• Category: Main Products
• Molecular Weight: 148.20
• Molecular Formula: C10H12O
• Synonyms: (Z)-1-Methoxy-4-(prop-1-en-1-yl)benzene
• Appearance: Pale yellow liquid

Case Study

(E)-/(Z)-Anethole as Photosensitized Isomerization Substrates for Stereoselective Diol Synthesis

Korff, Marvin, et al. Molecules 27.16 (2022): 5342.

(E)-Anethole, an abundant natural product of anise oil, acts as the substrate of a photocatalytic (E)-to-(Z) isomerization that converts it into the less accessible (Z)-anethole, a valuable precursor for diastereoselective synthesis in drug discovery.
Experimental Protocol: (E)-Anethole is dissolved in methanol together with 0.1 mol% of an iridium-based photosensitizer and irradiated at 400 nm overnight at 28°C under oxygen-free conditions, after which the catalyst is precipitated with n-pentane. Eleven photosensitizers are screened, with metal-based complexes proving superior to organo-photocatalysts. The resulting (Z)-anethole, containing about 10% of the (E)-isomer, is submitted to Upjohn dihydroxylation with osmium tetroxide in acetone and tert-butanol at room temperature.
Performance Evaluation: The photostationary state reaches a 10:90 (E):(Z) ratio, corresponding to 90% conversion on gram scale, and the recycled catalyst preserves this ratio after re-use. Reducing the catalyst loading from 2 to 0.1 mol% does not change the outcome, whereas shortening the irradiation to 8 h gives only 75% conversion. Dihydroxylation of (E)- and (Z)-anethole affords like- and unlike-configured diols in 96% and 62% yield, respectively. Density functional theory predicts triplet energies of 58.1 and 60.8 kcal/mol for the two isomers, guiding photosensitizer selection and confirming a clean transformation without side products.

Custom Q&A

What is the molecular formula of (Z)-anethole?

The molecular formula of (Z)-anethole is C10H12O.

What is the molecular weight of (Z)-anethole?

The molecular weight of (Z)-anethole is 148.20 g/mol.

Where is (Z)-anethole found in nature?

(Z)-anethole is found in Illicium verum, Limonia acidissima, and other organisms.

What is the IUPAC name of (Z)-anethole?

The IUPAC name of (Z)-anethole is 1-methoxy-4-[(Z)-prop-1-enyl]benzene.

What is the InChI key of (Z)-anethole?

The InChI key of (Z)-anethole is RUVINXPYWBROJD-ARJAWSKDSA-N.

How many hydrogen bond acceptor counts does (Z)-anethole have?

(Z)-anethole has one hydrogen bond acceptor count.

How many rotatable bond counts does (Z)-anethole have?

(Z)-anethole has two rotatable bond counts.

What is the topological polar surface area of (Z)-anethole?

The topological polar surface area of (Z)-anethole is 9.2Ų.

How many heavy atoms are present in (Z)-anethole?

(Z)-anethole has 11 heavy atoms.

Is (Z)-anethole a canonicalized compound?

Yes, (Z)-anethole is a canonicalized compound.