Ethyl 3-hydroxybutyrate

Synonym(s):grape butyrate

CAS NO.：5405-41-4
Empirical Formula: C6H12O3
Molecular Weight: 132.16
MDL number: MFCD00004545
EINECS: 226-456-2
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-20 11:41:24

What is 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.

Properties of Ethyl 3-hydroxybutyrate

Boiling point:	170 °C (lit.)
Density	1.017 g/mL at 25 °C (lit.)
refractive index	n20/D 1.42(lit.)
FEMA	3428 \| ETHYL 3-HYDROXYBUTYRATE
Flash point:	148 °F
storage temp.	Sealed in dry,2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Liquid
pka	14.45±0.20(Predicted)
color	Clear colorless
Odor	at 100.00 %. fruity green grape tropical apple skin
JECFA Number	594
BRN	1446190
CAS DataBase Reference	5405-41-4(CAS DataBase Reference)
NIST Chemistry Reference	Butanoic acid, 3-hydroxy-, ethyl ester(5405-41-4)
EPA Substance Registry System	Ethyl 3-hydroxybutyrate (5405-41-4)

Safety information for Ethyl 3-hydroxybutyrate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H227:Flammable liquids
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P280:Wear protective gloves/protective clothing/eye protection/face protection. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. P501:Dispose of contents/container to..…