whiskey lactone

Whiskey lactone, also known by its preferred chemical name 4-hydroxy-3-methyloctanoic acid gamma-lactone, is a lactone compound with the molecular formula C₉H₁₆O₂. It appears as a colorless to pale yellow liquid and is characterized by complex sensory notes including woody, coconut, nutty, and toasted nuances. It is a key contributor to the aroma profiles of many aged alcoholic beverages, especially aged whiskies. Whiskey lactone is identified by various synonyms such as oak lactone, gamma-whiskeylactone, and 3-methyl-4-octanolide. This compound is naturally extracted from oak wood, particularly Quercus species, during the maturation of spirits, and is also available via synthetic production methods. Controlled-vocabulary sources such as PubChem provide detailed chemical and structural information supporting its applications in the flavor and fragrance sectors.

Whiskey lactone occurs naturally in various aged alcoholic beverages including whiskey (both bourbon and Scotch), cognac, rum, sherry, port wine, and malt Irish malt. It is primarily derived from the oak barrels used during maturation, where the compound imparts distinctive woody and coconut-like aromatic characteristics. In formulation, whiskey lactone serves as a flavor and fragrance agent that enhances notes described as creamy, toasted, and nutty with a coumarinic undertone. Recognized under the FEMA (US) standard as FEMA number 3803, it has defined usage levels in flavorings, ensuring controlled incorporation in food and beverage products. Its presence contributes to the sensory complexity of spirits and various fragrance applications where woody and powdery odor profiles are desired.

Whiskey lactone exhibits a moderate molecular weight of approximately 156.22 g/mol and a molecular formula of C₉H₁₆O₂. The compound is a liquid at room temperature, with a refractive index ranging from 1.441 to 1.457 at 20°C, indicating moderate optical density. It has a specific gravity between 0.959 and 0.967 at 25°C, reflecting its density relative to water. The boiling point is measured between 93 to 94°C under reduced pressure (5 mm Hg), demonstrating volatility under vacuum conditions. Its vapor pressure at 25°C is low at 0.027 mmHg, suggesting limited evaporation under ambient conditions. The flash point is 212°F (approximately 100°C), denoting relative safety in handling under typical use. Solubility is favorable in alcohol and moderately soluble in water (about 1387 mg/L at 25°C), facilitating use in diverse matrices. Additionally, its estimated logP value of about 1.97 suggests moderate lipophilicity, influencing its behavior in formulations. Whiskey lactone maintains stability across various consumer product matrices such as creams, shampoos, and detergents, which supports its utility as a fragrance ingredient.

Leffingwell:	Chirality or Article
	5-butyl-4-methyloxolan-2-one
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	39212-23-2
Pubchem (cid):	62900
Pubchem (sid):	135143162
Pherobase:	View

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
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HMDB (The Human Metabolome Database):	Search
FooDB:	FDB014730
YMDB (Yeast Metabolome Database):	YMDB01605
Export Tariff Code:	2932.29.6000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
EFSA Update of results on the monitoring of furan levels in food:	Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:	Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:	Read Report

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for whiskey lactone usage levels up to:
	5.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU):		ND (μg/capita/day)
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 17
Click here to view publication 17
		average usual ppm	average maximum ppm
baked goods:		-	-
beverages(nonalcoholic):		0.50000	3.00000
beverages(alcoholic):		1.00000	5.00000
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		2.00000	10.00000
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	-
fruit ices:		-	-
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	-
hard candy:		1.00000	5.00000
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		-	-
snack foods:		-	-
soft candy:		-	-
soups:		-	-
sugar substitutes:		-	-
sweet sauces:		-	-

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf

Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC) View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): Aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 View page or View pdf

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EPA Substance Registry Services (TSCA):39212-23-2

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :62900

National Institute of Allergy and Infectious Diseases:Data

WGK Germany:2

5-butyl-4-methyloxolan-2-one

Chemidplus:0039212232