Whiskey lactone Chemical Properties

Boiling point:

93-94 °C5 mm Hg(lit.)

Density 

0.952 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.4454(lit.)

FEMA 

3803 | 4-HYDROXY-3-METHYLOCTANOIC ACID LACTONE

Flash point:

>230 °F

form 

clear liquid

color 

Colorless to Almost colorless

Odor

at 10.00 % in dipropylene glycol. tonka coumarin coconut toasted nutty celery burnt

Odor Type

tonka

JECFA Number

437

LogP

1.81

CAS DataBase Reference

39212-23-2(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-furanone, 5-butyldihydro-4-methyl-(39212-23-2)

EPA Substance Registry System

2(3H)-Furanone, 5-butyldihydro-4-methyl- (39212-23-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

2

HS Code 

2932190090

MSDS

• Language:English Provider:SigmaAldrich

Whiskey lactone Usage And Synthesis

Chemical Properties

Whiskey Lactone is found as its cis- and trans-isomers in whiskey and in oakwood volatiles; the cis-isomer is the more important in sensory terms. It is a clear, almost colorless liquid with an intense, warm, sweet, coumarin-like odor.
A cis–trans mixture can be prepared by radical addition reaction of pentanal with crotonic acid followed by reductive cyclization of the resulting ??-oxo acid with sodium boron hydride/sulfuric acid . It is used in aroma compositions, for example, for beverages.

Occurrence

Reported present in cognac, rum, Irish malt, bourbon whiskey, scotch, sherry, port and wine.

Definition

ChEBI: Quercuslactone a is a gamma-lactone.

Aroma threshold values

80% of a taste panel found whiskey lactone intolerable at 160 ppm

Taste threshold values

Taste characteristics at 0.5 ppm: woody, coumarinic, coconut, lactonic, creamy and nutty with a toasted nuance.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 6225, 1985 DOI: 10.1016/S0040-4039(00)95058-5

Trade name

Methyl octalactoneTM (PFW)

Whiskey lactone(39212-23-2)Related Product Information

• 2,3-Dihydrofuran
• Spironolactone
• D-(+)-Glucono-1,5-lactone
• 2-Butoxyethanol
• Diethylene glycol monobutyl ether
• Buprofezin
• Cyhalofop-butyl
• Butyl acetate
• TRIOXSALEN
• Butyl acrylate
• Hydroxy silicone oil
• 2,5-Dihydrofuran
• tert-Butyldimethylsilyl chloride
• gamma-Octanoic lactone
• (-)-Corey lactone diol
• 2,3-Dihydrobenzofuran
• tert-Butanol
• tert-Butyl methyl ether