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gamma-octalactone

Chemical Structure

General Material Information

Preferred name gamma-octalactone
Trivial Name γ-Octalactone
Short Description octano-1,4-lactone
Formula C8 H14 O2
CAS Number 104-50-7
Deleted CAS Number 57084-15-8
FEMA Number 2796
ECHA Number 203-208-1
FDA UNII UHD6M52X0K
Nikkaji Number J69.811C
Beilstein Number 0111677
MDL MFCD00005402
COE Number 2274
NMR Predictor External link
JECFA Food Flavoring 226 gamma-octalactone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 104-50-7 ; GAMMA-OCTALACTONE
Synonyms
  • 5-butyl dihydro-2(3H)-furanone
  • 5-butyl tetrahydro-2-furanone
  • 4-butyl-4-hydroxybutyric acid lactone
  • 4-N- butyl-4-hydroxybutyric acid lactone
  • 4-butyl-gamma-butyrolactone
  • gamma- butyl-gamma-butyrolactone
  • gamma-N- butyl-gamma-butyrolactone
  • 5-butyldihydro-2(3H)-furanone
  • 5-butyldihydrofuran-2(3H)-one
  • 5-butyloxolan-2-one
  • 2(3H)- furanone, 5-butyldihydro-
  • 2(3H)- furanone, dihydro-5-butyl-
  • 4-hydroxyoctanoic acid gamma-lactone
  • 4-hydroxyoctanoic acid lactone
  • gamma- octa lactone
  • g- octalactone
  • gamma octalactone
  • gamma- octalactone FCC
  • octalactone gamma
  • g- octalactone natural
  • gamma- octalactone natural
  • gamma- octalactone, natural
  • octan-4-olide
  • octano-1,4-lactone
  • octanoic acid gamma lactone
  • octanoic acid, 4-hydroxy-, lactone
  • gamma- octanolactone
  • 4-octanolide
  • octanolide-1,4
  • 5-butyloxolan-2-one
  • 2(3H)-Furanone, 5-butyldihydro-
  • Octanoic acid, 4-hydroxy-, γ-lactone
  • Caprylic acid, γ-hydroxy-, lactone
  • 5-Butyldihydro-2(3H)-furanone
  • γ-Octalactone
  • γ-Butyl-γ-butyrolactone
  • γ-Butylbutyrolactone
  • 4-Butyl-γ-butyrolactone
  • 4-Hydroxyoctanoic acid lactone
  • γ-Octanolactone
  • 4-Octanolide
  • 5-Butyl-1-oxacyclopentan-2-one
  • 5-Butyltetrahydro-2-furanone
  • (±)-4-n-Butylbutyrolactone
  • (RS)-γ-Octalactone
  • (±)-γ-Octalactone
  • NSC 24270
  • NSC 26509
  • γ-Caprylolactone

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

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Literature & References

5-butyloxolan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:104-50-7
Pubchem (cid):7704
Pubchem (sid):134972878
Flavornet:104-50-7
Pherobase:View
Publications by PubMed
Specific Volatile Compounds from Mango Elicit Oviposition in Gravid Bactrocera dorsalis Females.
Oviposition site-selection by Bactrocera dorsalis is mediated through an innate recognition template tuned to γ-Octalactone.
6-Pentyl-2H-pyran-2-one: a potent peach-derived kairomone for New Zealand flower thrips, Thrips obscuratus.
Effect of α-tocopherol on lactone formation in marbled beef and changes in lactone volatility during storage.
Isolation and identification of host cues from mango, Mangifera indica, that attract gravid female oriental fruit fly, Bactrocera dorsalis.
Artificial aging of Uva di Troia and Primitivo wines using oak chips inoculated with Penicillium purpurogenum.
Effects of alpha-tocopherol on lactones in beef headspace during storage.
Use of microfungi in the treatment of oak chips: possible effects on wine.
Expression of genes associated with aroma formation derived from the fatty acid pathway during peach fruit ripening.
Fate of key odorants in Sauternes wines through aging.
Comparison of urinary scents of two related mouse species, Mus spicilegus and Mus domesticus.
Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage.
Odor detection thresholds and enantiomeric distributions of several 4-alkyl substituted gamma-lactones in Australian red wine.
Quantification of several 4-alkyl substituted gamma-lactones in Australian wines.
Effect of grain type and toasting conditions of barrels on the concentration of the volatile substances released by the wood and on the sensory characteristics of Montepulciano d'Abruzzo.
Aroma extraction dilution analysis of Sauternes wines. Key role of polyfunctional thiols.
Aroma composition of red wines by different extraction methods and Gas Chromatography-SIM/MASS spectrometry analysis.
Effect of fat nature and aroma compound hydrophobicity on flavor release from complex food emulsions.
Composition rather than viscosity modifies the aroma compound retention of flavored stirred yogurt.
Volatile compounds in a spanish red wine aged in barrels made of Spanish, French, and American oak wood.
Influence of distillation system, oak wood type, and aging time on volatile compounds of cider brandy.
Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry.
Prediction of aged red wine aroma properties from aroma chemical composition. Partial least squares regression models.
Comparison of direct and indirect methods of measuring the precursors of beta-methyl-gamma-octalactone and their application to the analysis of Sessile oak wood.
Identification of a precursor of beta-methyl-gamma-octalactone in the wood of sessile oak (Quercus petraea (Matt.) Liebl.).
Influence of storage conditions on the formation of some volatile compounds in white fortified wines (Vins doux naturels) during the aging process.
Chirality of the gamma-lactones produced by Sporidiobolus salmonicolor grown in two different media.

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):HMDB35422
FooDB:FDB014100
Export Tariff Code:2932.29.6000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider: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

Suppliers

ACS International Advanced Biotech
Alfrebro Ambles Nature et Chimie
Anhui Haibei Apple Flavor & Fragrance
Artiste Astral Extracts
Augustus Oils Aurochemicals
Axxence Aromatic Bedoukian Research
Beijing Lys Chemicals Bell Flavors & Fragrances
Berjé BOC Sciences
Citrus and Allied Essences Creatingperfume.com
De Monchy Aromatics Diffusions Aromatiques
ENNOLYS Ernesto Ventós
Excellentia International Fleurchem
IFF Indenta Group
Indukern F&F Inoue Perfumery
Jiangyin Healthway K.L. Koh Enterprise
Kingchem Laboratories Kun Shan P&A
Liaison Carbone Lluch Essence
M&U International Mane
Moellhausen Natural Advantage
Naturamole Oamic Ingredients
Odowell Co.,ltd Omega Ingredients
OQEMA Pell Wall Perfumes
Penta International Perfumer Supply House
PerfumersWorld Phoenix Aromas & Essential Oils
Primechem Prodasynth
Quimdis R C Treatt & Co Ltd
Reincke & Fichtner Riverside Aromatics
Robertet Sigma-Aldrich
Soda Aromatic SRS Aromatics
Sunaux International Synerzine
TCI AMERICA The Good Scents Company
The Lermond Company The Perfumers Apprentice
United International Vigon International
WEN International WholeChem
ACS International GmbH Advanced Biotech. Inc.
Alfrebro LLC/ Archer Daniels Midland Company Augustus Oils Ltd
Axxence Aromatic GmbH Bedoukian Research, Inc.
Beijing Lys Chemicals Co, LTD. Berje Inc.
Lesaffre Yeast Corporation/ENNOLYS Fleurchem, Inc.
Indukern, S.A. F&F Ingredients Division Jiangyin Healthway International Trade Co., Ltd
Lluch Essence S.L. M&U International LLC
Moellhausen S.P.A. Penta International Corporation
PerfumersWorld Ltd. Anhui Primechem Co., Ltd.
Riverside Aromatics Ltd. Robertet, Inc.
Soda Aromatic Co., Ltd. SRS Aromatics Ltd
Synerzine, Inc. R C Treatt and Co Ltd
Qingdao Free Trade Zone United International Co Ltd Ernesto Ventós S.A.
WholeChem, LLC

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 142.19798278809
Specific gravity @ 25 °C
Pounds per Gallon 8.071 to 8.155
Refractive Index 1.443 to 1.447 @ 20 °C
Boiling Point 132 to 133°C @ 20 mm Hg
Acid Value 8 max KOH/g
Vapor Pressure 0.041 mmHg @ 25 °C
Vapor Density 1
Flash Point TCC Value 110 °C TCC
logP (o/w) 1.432 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
dipropylene glycol Yes
water, slightly Yes
water, 3632 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Coconut
sweet, coconut, waxy, creamy, tonka, dairy, fatty, milky, soapy, coumarinic, fruity, peach, apricot
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 144 hour(s) at 100.00 %
Luebke, William tgsc, (1998) At 10.00 % in dipropylene glycol. sweet coconut waxy creamy tonka dairy fatty
Mosciano, Gerard P&F 21, No. 1, 33, (1996) Sweet, creamy, coconut, milky, soapy, coumarin, fruity, peach and apricot
Flavor Type: Lactonic
lactonic, coconut, creamy, toasted, coumarinic, fruity, apricot, peach
Mosciano, Gerard P&F 21, No. 1, 33, (1996) At 10.00 ppm. Lactonic, coconut, creamy, toasted, coumarin, fruity, apricot and peach
Lactone notes for a variety of flavors, especially coconut, vanilla, cream, as well as sweet dairy, fruits such as mango, peach, and apricot. Characteristic coconut meat with vanilla coumarin notes

Occurrences

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 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
Skin irritation (Category 2), H315
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
H315 - Causes skin irritation
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
12 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 4400 mg/kg
Food and Cosmetics Toxicology. Vol. 14, Pg. 821, 1976.

oral-rat LD50 > 5000 mg/kg
(Moreno, 1974c)

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
(Moreno, 1974c)

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 gamma-octalactone usage levels up to:
12.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 430.00 (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: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -17.00000
beverages(nonalcoholic): -4.80000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -16.00000
fruit ices: -16.00000
gelatins / puddings: -15.00000
granulated sugar: --
gravies: --
hard candy: -16.00000
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):104-50-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7704
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
5-butyloxolan-2-one
Chemidplus:0000104507
RTECS:LU3562000 for cas# 104-50-7