39212-23-2

Basic information

• Product Name: Whiskey lactone
• Synonyms: WHISKEY LACTONE;WHISKY LACTONE;5-butyldihydro-4-methyl-2(3h)-furanon;FEMA 3803;METHYL OCTALACTONE;METHYL OCTALACTONE(TM);(+/-)-5-BUTYL-4-METHYLDIHYDRO-2(3H)-FURANONE;5-BUTYLDIHYDRO-4-METHYL-2(3H)-FURANONE
• CAS NO: 39212-23-2
• Molecular Formula: C₉H₁₆O₂
• Molecular Weight: 156.22
• EINECS: 254-357-4
• Mol File: 39212-23-2.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 93-94 °C5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.952 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.027mmHg at 25°C
• Refractive Index: n20/D 1.4454(lit.)
• CAS DataBase Reference: Whiskey lactone(CAS DataBase Reference)
• NIST Chemistry Reference: Whiskey lactone(39212-23-2)
• EPA Substance Registry System: Whiskey lactone(39212-23-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 2
• Hazardous Substances Data: 39212-23-2(Hazardous Substances Data)

Usage

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.

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)

InChI:InChI=1/C9H16O2/c1-3-4-5-8-7(2)6-9(10)11-8/h7-8H,3-6H2,1-2H3

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 65038-34-8 3-formyl-butyric acid methyl ester 
• 109-72-8 n-butyllithium 
• 127459-10-3 (4R,5R)-5-Butyl-4-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 110-62-3 pentanal 
• 59086-42-9 3-methyl-4-oxo-octanoic acid 
• 142685-47-0 3-methyl-4-oxo-octanoic acid ethyl ester 
• 77734-07-7 2-Butyltetrahydro-3-furancarbaldehyd 
• 93828-03-6 (3R*,4R*)-4-hydroxy-3-methyl-1-octene 
• 30336-14-2 5-butylfuran-2(5H)-one 
• 152930-87-5 1-Bromo-2-ethoxy-2-(1-heptene-3-oxy)ethane 
• 4938-52-7 1-hepten-3-ol 
• 126188-65-6 4-methyl-5-(n-butyl)-2(5H)-furanone 
• 31705-09-6 (2α,3α)-(+/-)-2-Butyltetrahydro-3-methylfuran 

Downstream Products

• 105119-22-0 (4R,5S)-trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 
• 87433-99-6 C₄H₄O₂(CH₂HgBr)(CH₂CH₂CH₂CH₃) 
• 87434-00-2 CH₃OOCCH₂CH(CH₂HgBr)CH(OOCCF₃)CH₂CH₂CH₂CH₃ 
• 104910-76-1 (3S,4S)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester 
• 105015-54-1 (3R,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester 
• 104910-74-9 (3R,4R)-3-Methyl-4-<(R)-2-phenylpropionyloxy>octansaeure-isopropylester 
• 105015-50-7 (3S,4S)-3-Methyl-4-<(R)-2-phenylpropionyloxy>octansaeure-isopropylester 
• 105015-55-2 (3R,4S)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester 
• 105015-56-3 (3S,4R)-3-Methyl-4-<(1'S,4'R)-4',7',7'-trimethyl-3'-oxo-2'-oxabicyclo<2.2.1>heptan-1'-ylcarbonyloxy>octansaeure-isopropylester 
• 105015-51-8 (3S,4R)-3-Methyl-4-<(R)-2-phenylpropionyloxy>octansaeure-isopropylester 
• 105015-52-9 (3R,4S)-3-Methyl-4-<(R)-2-phenylpropionyloxy>octansaeure-isopropylester 

Relevant articles and documents

Exploiting the vicinal disubstituent effect on the diastereoselective synthesis of γ and δ lactones

Trifluoroacetic acid catalysed lactonization of vicinal disubstituted γ-hydroxyesters was investigated in different solvents. The reaction kinetics, monitored by NMR spectroscopy, showed that: (i) the vic-disubstituent effect is stereoselective since the anti diastereoisomer ring closes substantially more rapidly than the syn isomer ring; (ii) the anti-vic effect is much stronger than the classical Thorpe-Ingold effect (known also as the gem-disubstituent effect), instead the syn diastereoisomers have rate constants comparable to that of the gem-disubstituted ester; (iii) the vic-effect can be enhanced by increasing the steric hindrance of one of the two substituents or carrying out the reaction in non-polar solvents. DFT computations of energy barriers (ΔG?) were in good agreement with the experimental data. The distortion/interaction-activation strain model together with the Winstein-Holness kinetic scheme gave more insights into the origin of the vic-effect. An application of this effect consists of the diastereomeric resolution of disubstituted γ and δ lactones, among which are the naturally occurring Nicotiana t. lactone, the whisky and cognac oak lactones, and the Aerangis lactone. Both cis and trans diastereoisomers of these lactones were isolated in good yield and with high diastereomeric excess (de >92%). The selectivities of the diastereomeric resolution process, determined by NMR spectroscopy, are reported as well.

PROCESS FOR THE ELECTROCHEMICAL PREPARATION OF GAMMA-HYDROXYCARBOXYLIC ESTERS AND GAMMA-LACTONES

γ-Hydroxycarboxylic esters and γ-lactones which are suitable as flavors can be prepared by electrochemical reductive cross-coupling of α,β-unsaturated esters with carbonyl compounds in an undivided electrolysis cell having a cathode composed of lead, lead alloys, cadmium, cadmium alloys, mercury, steel, glassy carbon or boron-doped diamonds and a basic aqueous electrolyte comprising an electrolyte salt which suppresses the cathodic formation of hydrogen.

An expedient synthesis of olfactory lactones by intramolecular hydroacylalkoxylation reactions

A series of 4,5-disubstituted γ-lactones, including whisky and cognac lactones, was synthesised in four steps from a readily available chiral precursor. By using an intramolecular hydroacylalkoxylation reaction in the final step, a correlation between the (E)/(Z) configuration of the precursor and the product distribution has been established, for the first time, in this type of cyclisation reactions. Copyright