cis-Anethol
[CAS# 104-46-1]

Identification

• Classification: API >> Blood system medication >> Leukocyte proliferative drug
• Name: cis-Anethol
• Synonyms: 1-Methoxy-4-[(Z)-prop-1-enyl]benzene
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.20
• CAS Registry Number: 104-46-1
• EC Number: 203-205-5
• SMILES: C/C=C/C1=CC=C(C=C1)OC

Properties

• Solubility: 10mM (DMSO) (Expl.)
• Density: 1.0±0.1 g/cm³, Calc.^*, 0.987 g/mL (Expl.)
• Melting point: 20 � 23 ºC (Expl.)
• Index of Refraction: 1.545, Calc.^*
• Boiling Point: 237.5±9.0 ºC (760 mmHg), Calc.^*, 232 � 235 ºC (EXpl.)
• Flash Point: 90.6 ºC, Calc.^*, 96 ºC (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H317
• Precautionary Statements: P261-P272-P280-P302+P352-P321-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovory and Applicatios

Cis-anethol is a chemical compound that belongs to the class of phenylpropanoids, which are naturally occurring organic compounds often found in essential oils of plants. It is a structural isomer of trans-anethol and is most commonly known for its presence in the essential oils of anise, fennel, and star anise, contributing to their characteristic aroma and flavor. Cis-anethol is a key component in the production of various aromatic products, including perfumes, food flavorings, and traditional medicines.

The discovery of cis-anethol, like many natural aromatic compounds, arose from the study of plant-derived substances, particularly those used in culinary and medicinal applications. The compound is most notably recognized for its sweet, licorice-like scent, which has made it an essential ingredient in the fragrance and flavor industry. Its identification and isolation were part of early research into the volatile compounds that contribute to the sensory properties of essential oils.

In terms of its chemical structure, cis-anethol is an aromatic compound with a methoxy group (-OCH3) and a propene side chain. It is a liquid at room temperature and is typically colorless to pale yellow. Its molecular formula is C10H12O, and it has a molecular weight of 148.2 g/mol. The compound is known for its stability and relatively low toxicity, making it suitable for use in a variety of consumer products.

Cis-anethol is primarily used in the fragrance and flavor industries. As a component of essential oils, it is used to impart a sweet, anise-like flavor to foods and beverages. It is commonly found in licorice-flavored candies, gum, and herbal teas. In addition, cis-anethol is often utilized in the production of perfumes and cosmetics due to its pleasant scent. The compound's ability to mimic the flavor and aroma of aniseed has made it a valuable ingredient in both the culinary and cosmetic fields.

Beyond its use in flavors and fragrances, cis-anethol has also been investigated for its potential pharmacological properties. It has been studied for its potential antimicrobial, antioxidant, and anti-inflammatory effects. Some studies have suggested that cis-anethol may possess modest antibacterial and antifungal properties, contributing to its historical use in traditional medicine for treating digestive issues and respiratory conditions. However, while these applications are recognized, further clinical research is needed to fully establish its therapeutic efficacy.

In addition to its use in food and fragrance products, cis-anethol is also utilized in certain industrial applications, particularly in the synthesis of other chemicals. It serves as a precursor in the production of various derivatives, such as anethole derivatives, which have applications in both pharmaceuticals and chemical manufacturing.

In conclusion, cis-anethol is a well-established compound known for its role in the flavor and fragrance industries. Its distinctive anise-like aroma and flavor have made it a widely used ingredient in both food products and cosmetics. While its pharmacological properties continue to be explored, cis-anethol's primary applications remain in the production of aromatic products.

References

Lastra-Barreira, B. and Crochet, P., 2010. Ruthenium-catalyzed estragole isomerization: high trans-selective formation of anethole. Green Chemistry, 12, 1311.
DOI: 10.1039/c003901b

Lastra-Barreira, B., Francos, J., Crochet, P. and Cadierno, V., 2011. Ruthenium(iv) catalysts for the selective estragole to trans-anethole isomerization in environmentally friendly media. Green Chemistry, 13, 307.
DOI: 10.1039/c0gc00417k

Jinesh, C. M., Sen, A., Ganguly, B. and Kannan, S., 2012. Microwave assisted isomerization of alkenyl aromatics over solid base catalysts: an understanding through theoretical study. RSC Advances, 2, 6871.
DOI: 10.1039/c2ra20179h