ETHYL CROTONATE

Chemical properties

clear colorless liquid

Chemical properties

Ethyl crotonate has a powerful, sour, caramellic-fruity odor.

Occurrence

Reported found in Fragaria vesca. Also reported found in guava fruit, guava peel, pineapple, white wine, yellow passion fruit, fresh mango, naranjilla fruit, mussel, loganberry, apple, papaya, concord grape, strawberry, rum, cocoa, plum, kiwifruit and other natural sources.

The Uses of ETHYL CROTONATE

Crotonic Acid Ethyl Ester, is an intermediate for the preparation of various pharmaceutical compounds. It can be used for the synthesis of (+)-trans-Trikentrin A.

Preparation

By esterification of crotonic acid with ethyl alcohol in the presence of concentrated H2SO4.

Definition

ChEBI: Ethyl crotonate is a fatty acid ester.

Taste threshold values

Taste characteristics at 10 ppm: rum, cognac and pungent with caramellic and fruity nuances.

Synthesis Reference(s)

Journal of the American Chemical Society, 112, p. 2716, 1990 DOI: 10.1021/ja00163a038
Synthetic Communications, 14, p. 701, 1984 DOI: 10.1080/00397918408059583

General Description

A clear colorless liquid with a pungent odor. Flash point 36°F. Less dense than water and insoluble in water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

ETHYL CROTONATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Slightly toxic by ingestion. Corrosive. An eye irritant and lachrymator. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.