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

Description

Whiskey lactone is a chemical compound found in various alcoholic beverages and oakwood volatiles, known for its intense, warm, sweet, and coumarin-like odor. It occurs in both cisand trans-isomers, with the cis-isomer being more significant in sensory terms. Whiskey lactone is a clear, almost colorless liquid with taste threshold values that contribute to the woody, coumarinic, coconut, lactonic, creamy, and nutty flavor profile with a toasted nuance at 0.5 ppm.

Uses

Used in Beverage Industry:
Whiskey lactone is used as a flavoring agent for beverages, particularly in the production of whiskey, rum, Irish malt, bourbon whiskey, Scotch, sherry, port, and wine. It imparts a unique woody, coumarinic, coconut, lactonic, creamy, and nutty taste with a toasted nuance, enhancing the overall flavor profile of these drinks.
Used in Aroma Compositions:
Whiskey lactone is also used in the creation of aroma compositions, where its intense, warm, sweet, and coumarin-like odor adds depth and complexity to fragrances. This application takes advantage of the compound's ability to evoke a range of taste characteristics, making it a valuable addition to the world of aromas and perfumes.
Production Methods:
A cis-trans mixture of whiskey lactone can be prepared through a radical addition reaction of pentanal with crotonic acid, followed by reductive cyclization of the resulting ??-oxo acid with sodium boron hydride/sulfuric acid. This process allows for the synthesis of whiskey lactone, which can then be used in various applications across different industries.

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

• 110-62-3 pentanal 
• 91075-13-7 (Z)-2-Dimethylamino-pent-2-enenitrile 
• 104310-49-8 (4S,5R)-3,3-Dichloro-5-(3,4-dimethoxy-phenyl)-4-methyl-5-p-tolylsulfanyl-dihydro-furan-2-one 
• 922-69-0 1,1-dimethoxyethylene 
• 623-43-8 methyl crotonate 
• 10544-63-5 ethyl crotonate 
• 142685-47-0 3-methyl-4-oxo-octanoic acid ethyl ester 
• 693-03-8 n-butyl magnesium bromide 
• 65038-34-8 3-formyl-butyric acid methyl ester 
• 109-72-8 n-butyllithium 
• 30336-14-2 5-butylfuran-2(5H)-one 
• 917-54-4 methyllithium 
• 24406-16-4 lithium di-n-butylcuprate 
• 693-04-9 butyl magnesium bromide 

Downstream Products

• 105119-22-0 (4R,5S)-trans-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 
• 80041-01-6 (+)-trans-whisky lactone 
• 80041-00-5 (4S,5S)-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 
• 105015-53-0 (4R,5R)-5-n-butyl-4-methyl-4,5-dihydro-2(3H)-furanone 
• 104910-77-2 i‐propyl‐4‐hydroxy‐3‐methyloctanoate 
• 104910-75-0 i‐propyl‐4‐hydroxy‐3‐methyloctanoate 
• 87434-05-7 erithro-3-methyl-1,4-octandiol 
• 87434-02-4 (3RS,4SR)-3-methyloctan-1,4-diol 
• 741717-02-2 (3S,4R)-1-t-butyldiphenylsilyloxy-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octane 
• 741717-01-1 (3R,4S)-1-t-butyldiphenylsilyloxy-3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octane 
• 741716-99-4 (3R,4R)-3-methyl-4-O-β-D-glucopyranosyloctanoic acid 
• 173355-98-1 (3S,4S)-3-methyl-4-O-β-D-glucopyranosyloctanoic acid 
• 741716-98-3 (3R,4R)-benzyl 3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octanoate 
• 741716-97-2 (3S,4S)-benzyl 3-methyl-4-O-(2',3',4',6'-tetra-O-pivaloyl-β-D-glucopyranosyl)octanoate 

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