Whiskey lactone

Whiskey lactone
  • CAS No.:39212-23-2
Other grades of this product :
Whiskey lactone Basic information
Product Name:Whiskey lactone
Synonyms:beta-Methyl-gamma-octanolactone;5-butyl-4-methyloxolan-2-one;WHISKEY LACTONE;rac-(3R*,4S*)-3-Methyl-4-hydroxyoctanoic acid 1,4-lactone;rac-(4R*)-4β*-Methyl-5α*-butyloxolane-2-one;rac-(4S*,5R*)-4α*-Methyl-5β*-butyl-4,5-dihydrofuran-2(3H)-one;rac-5β*-Butyldihydro-4α*-methyl-2(3H)-furanone;trans-Oak lactone
CAS:39212-23-2
MF:C9H16O2
MW:156.22
EINECS:254-357-4
Product Categories:
Mol File:39212-23-2.mol
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
Fp >230 °F
form clear liquid
color Colorless to Almost colorless
JECFA Number437
CAS DataBase Reference39212-23-2(CAS DataBase Reference)
NIST Chemistry Reference2(3H)-furanone, 5-butyldihydro-4-methyl-(39212-23-2)
EPA Substance Registry System2(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 Information
ProviderLanguage
SigmaAldrich English
Whiskey lactone Usage And Synthesis
Chemical PropertiesWhiskey 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.
OccurrenceReported present in cognac, rum, Irish malt, bourbon whiskey, scotch, sherry, port and wine.
Aroma threshold values80% of a taste panel found whiskey lactone intolerable at 160 ppm
Taste threshold valuesTaste 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 nameMethyl octalactoneTM (PFW)
Whiskey lactone Preparation Products And Raw materials

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