2-(3,4-Dihydroxyphenyl)ethyl acetate
[CAS# 69039-02-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Phenols, ethers and epoxides >> Phenolic flavors
• Name: 2-(3,4-Dihydroxyphenyl)ethyl acetate
• Synonyms: 4-[2-(Acetyloxy)ethyl]-1,2-benzenediol; Hydroxytyrosol acetate
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.20
• CAS Registry Number: 69039-02-7
• SMILES: CC(=O)OCCC1=CC(=C(C=C1)O)O

Properties

• Density: 1.260
• Boiling point: 356 °C
• Flash point: 142 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P351-P302+P352

Discovery and Applications

2-(3,4-Dihydroxyphenyl)ethyl acetate, also known as dihydrocaffeic acid acetate or hydroxytyrosol acetate, is a naturally occurring phenolic compound. Its discovery dates back to the 20th century research on plant metabolites, when it was found in olives, olive oil, and other sources of hydroxytyrosol. The acetate form is believed to be a product of natural acetylation, which enhances the stability and lipophilicity of the compound.

The main application of 2-(3,4-dihydroxyphenyl)ethyl acetate is as an antioxidant. Its structure has dihydroxy groups that are effective in scavenging free radicals. This makes it valuable in food preservation, where it protects oils and other products from oxidation, extending shelf life and maintaining nutritional quality.

In the cosmetic industry, this compound is used to protect the skin from oxidative stress and environmental damage due to its antioxidant properties. It is used in anti-aging creams, serums, and lotions to help maintain the healthy appearance of the skin by neutralizing harmful free radicals.

In the pharmaceutical field, 2-(3,4-dihydroxyphenyl)ethyl acetate shows promise for its potential health benefits. Research suggests that it may have anti-inflammatory, anticancer, and cardioprotective properties similar to hydroxytyrosol. Its ability to modulate oxidative stress and inflammation suggests that it has potential for treating chronic diseases such as cardiovascular disease and neurodegenerative diseases.

The compound is also incorporated into functional foods and dietary supplements for its health-promoting benefits. As a derivative of hydroxytyrosol, it helps improve the antioxidant capacity of these products, supporting overall health and potentially reducing the risk of chronic disease.

In scientific studies, 2-(3,4-dihydroxyphenyl)ethyl acetate is used as a model compound to study antioxidant mechanisms and the effects of acetylation on biological activity. Its structure provides a foundation for the development of new antioxidants and exploring the relationship between structure and function of phenolic compounds.

References

2024. Discovery of xanthine oxidase inhibitors from Olea europaea L. fruit with antioxidant activity by affinity ultrafiltration guided by molecular docking assay. Journal of Food Measurement and Characterization, 18(8).
DOI: 10.1007/s11694-024-02830-1

2011. 3,4-Dihy-droxy-phenethyl acetate. Acta crystallographica. Section E, Structure reports online, 67(8).
DOI: 10.1107/s1600536811026730

2002. Phenolic Compounds Profile of Cornicabra Virgin Olive Oil. Journal of Agricultural and Food Chemistry, 50(22).
DOI: 10.1021/jf0205211