Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

. A colorless liquid at room temperature, it has the semi-developed formula of CH₃(CH₂)₆COOCH₂CH₃, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

Synthesis

Ethyl octanoate can be synthesized from caprylic acid and ethanol via a classic

Fischer–Speier esterification Fischer esterification or Fischer–Speier esterification is a special type of esterification by refluxing a carboxylic acid and an Alcohol (chemistry), alcohol in the presence of an acid catalyst. The reaction was first described by Emil Fischer ...

. : Equilibrium can be shifted towards the right side of the equation through removal of water.

Uses

Ethyl octanoate does not see widespread use due to the greater availability of reasonably similar esters such as

ethyl acetate Ethyl acetate commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This flammable, colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues, nail polish removers, ...

. However, there are certain applications where it fills a niche. Ethyl octanoate has a strong odor of fruit and flowers and a taste of apricot, and as such it can be used as a flavoring or to create scents. It sees some use as a cleaning agent. Ethyl octanoate also sees incidental use. It is found in some

wine Wine is an alcoholic drink made from Fermentation in winemaking, fermented fruit. Yeast in winemaking, Yeast consumes the sugar in the fruit and converts it to ethanol and carbon dioxide, releasing heat in the process. Wine is most often made f ...

s, where overall ester concentration and composition is considered important to the flavor and aroma profile.Marais, J. et al. (2003) http://www.sawislibrary.co.za/dbtextimages/MaraisJ10.pdf "Effect of Different Wine-Making Techniques on the Composition and Quality of Pinotage Wine. I. Low-Temperature Skin Contact Prior to Fermentation"

Safety

Like many esters, ethyl octanoate is not considered to be toxic. LD50 in rats is 25.96 g/kg. Though it has a low explosive limit of only 0.67 vol%, it is also weakly volatile, with a vapor pressure of only 0.2 mbar at room temperature. Ethyl octanoate is combustible.

References

{{Esters Octanoate esters Ethyl esters