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whiskey lactone

Chemical Structure

General Material Information

Preferred name whiskey lactone
Trivial Name Whiskey lactone
Short Description 4-hydroxy-3-methyloctanoic acid gamma-lactone
Formula C9 H16 O2
CAS Number 39212-23-2
FEMA Number 3803
Flavis Number 10.053
ECHA Number 254-357-4
FDA UNII HKX8Y5BUAO
Nikkaji Number J47.448G
MDL MFCD00209540
COE Number 10535
xLogP3-AA 2.50 (est)
NMR Predictor External link
JECFA Food Flavoring 437 4-hydroxy-3-methyloctanoic acid gamma-lactone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 39212-23-2 ; 4-HYDROXY-3-METHYLOCTANOIC ACID LACTONE
Synonyms
  • 5-butyl dihydro-4-methyl furan-2(3H)-one
  • 5-butyl dihydro-4-methyl-2(3H)-furanone
  • 5-butyl-4-methyl dihydro-2(3H)-furanone
  • 5-butyl-4-methyl-3,4,5-trihydrofuran-2-one
  • 5-butyl-4-methyldihydro-2(3H)-furanone
  • 5-butyl-4-methyldihydrofuran-2(3H)-one
  • 5-butyl-4-methyloxolan-2-one
  • 5-butyldihydro-4-methyl-2(3H)-furanone
  • 5-butyldihydro-4-methylfuran-2(3H)-one
  • 2(3H)- furanone, 5-butyldihydro-4-methyl-
  • hydroxy-3-methyl octanoic acid lactone
  • 4-hydroxy-3-methyl octanoic acid lactone
  • 4-hydroxy-3-methyloctanoic acid gamma-lactone
  • methyl octalactone (PFW)
  • 3-methyl-4-octanolide
  • beta- methyl-alpha-octalactone
  • 3-methyl-gamma-octalactone
  • 3-methyloctano-1,4-lactone
  • oak lactone
  • oaklactone
  • quercus lactone
  • whiskey lactone synthetic
  • whiskeylactone
  • gamma- whiskeylactone
  • whisky lactone
  • 5-butyl-4-methyloxolan-2-one
  • 2(3H)-Furanone, 5-butyldihydro-4-methyl-
  • 5-Butyldihydro-4-methyl-2(3H)-furanone
  • β-Methyl-γ-octalactone
  • 3-Methyl-4-octanolide
  • 3-Methyloctano-4-lactone
  • 5-Butyl-4-methyldihydrofuran-2(3H)-one

US / EU / FDA / JECFA / FEMA / Scholar / Patents

Google Scholar Start search
Google Books Start search
Google Patents Start search
Perfumer & Flavorists Start search
EU Patents Start search
PubMeb Start search
NCBI Start search

Literature & References

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
Publications by Perfumer & Flavorist
Organoleptic Characteristics of Flavor Materials
Publications by Google Patents
Process for producing cis-whiskey-lactone
Publications by PubMed
Gas chromatography with mass spectrometry as a useful approach for the differentiation of wines according to geographical origin based on global volatile patterns.
Determination of lactones in wines by headspace solid-phase microextraction and gas chromatography coupled with mass spectrometry.
Interactions of odorants with olfactory receptors and receptor neurons match the perceptual dynamics observed for woody and fruity odorant mixtures.
Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.
Volatile compounds of red wines macerated with Spanish, American, and French oak chips.
Importance of chip selection and elaboration process on the aromatic composition of finished wines.
Analytical characterization of the aroma of five premium red wines. Insights into the role of odor families and the concept of fruitiness of wines.
Influence of geographical origin and botanical species on the content of extractives in American, French, and East European oak woods.
Aroma composition of red wines by different extraction methods and Gas Chromatography-SIM/MASS spectrometry analysis.
Synthesis and analysis of thio-, thiono-, and dithio-derivatives of whiskey lactone.
Quantitative gas chromatography-olfactometry carried out at different dilutions of an extract. Key differences in the odor profiles of four high-quality Spanish aged red wines.
Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions.

Other Information

(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
FDA Substances Added to Food (formerly EAFUS):View
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

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 156.22491455078
Specific gravity @ 25 °C
Pounds per Gallon 7.98 to 8.046
Refractive Index 1.441 to 1.457 @ 20 °C
Boiling Point 93 to 94°C @ 5 mm Hg
Vapor Pressure 0.027 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 1.968 est
Solubility
alcohol Yes
water, 1387 mg/L @ 25 °C (est) Yes
water No
Stability
alcohol Good
cream rinse Excellent
deo pump spray Good
detergent powder Good
fabric softener Good
hand cream Excellent
liquid detergent Good
shampoo Good
soap Good
liquid bleach Moderate

Organoleptic Properties

Odor Type: Tonka
tonka, coumarinic, coconut, toasted, nutty, celery, burnt, lactonic, woody, maple, lovage
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 59 hour(s) at 100.00 %
Luebke, William tgsc, (2007) At 10.00 % in dipropylene glycol. tonka coumarin coconut toasted nutty celery burnt
Mosciano, Gerard P&F 22, No. 2, 69, (1997) Coumarinic, coconut, Iactonic, woody, maple and lovage with a slightly toasted, nutty nuance
Flavor Type: Woody
woody, coumarinic, coconut, lactonic, creamy, nutty, toasted
Mosciano, Gerard P&F 22, No. 2, 69, (1997) At 0.50 ppm. Woody, coumarinic, coconut, Iactonic, creamy and nutty with a toasted nuance
Beverages, Alcoholic Spirits, Hard Candy Woody, Coconut, Creamy and Nutty with Toasted Nuance
General comment Winey coco

Occurrences

Potential Uses

Applications
Odor purposes Coconut, Floral, Fruit, Maple, Powder, Woody
Flavoring purposes Chocolate cocoa, Whiskey
Cosmetic purposes Perfuming agents

Safety Information

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 ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 0.500003.00000
beverages(alcoholic): 1.000005.00000
breakfast cereal: --
cheese: --
chewing gum: 2.0000010.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 1.000005.00000
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

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
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