Ethyl 3-hydroxybutyrate

Chemical properties

Ethyl-3-hydroxybutyrate is a clear colorless viscous liquid and has a fresh, fruity, grape odor. It is one of the main aroma components of wine. It occurs naturally in fruits such as pineapple, tamarillo fruit, caja fruit and naranjilla fruit.

Occurrence

Reported found in passion fruit, rum, sherry, wine, orange juice, guava, pineapple, tea, mango, wood apple, mountain papaya, naranjilla fruit, quince and hog plum (Spondias mombins L.)

The Uses of Ethyl 3-hydroxybutyrate

Ethyl 3-hydroxybutyrate is a fragrance found in wine and Tribolium castaneum. It is a reagent used to synthesize α-azido carboxylic acids. It is also used in Palladium mediated spiroketal synthesis.

Definition

ChEBI: Ethyl 3-hydroxybutyrate is the fatty acid ethyl ester of 3-hydroxybutyric acid. It has a role as a metabolite. It derives from a 3-hydroxybutyric acid.

Preparation

Ethyl 3-hydroxybutyrate is synthesized by catalytic hydrogenation of ethyl acetoacetate.

Taste threshold values

Taste characteristics at 30 ppm: green, fruity and winy.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 3966, 1970 DOI: 10.1021/jo00836a087
Tetrahedron Letters, 31, p. 1615, 1990 DOI: 10.1016/0040-4039(90)80031-G

General Description

Ethyl 3-hydroxybutyrate is a clear colorless liquid. (NTP, 1992)

Air & Water Reactions

Water soluble.

Reactivity Profile

Ethyl 3-hydroxybutyrate is incompatible with strong oxidizing agents and strong bases.

Fire Hazard

Ethyl 3-hydroxybutyrate is combustible.