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General Material Information

Preferred name gamma-butyrolactone
Trivial Name γ-Butyrolactone
Short Description 4-hydroxybutyric acid lactone
Formula C4 H6 O2
CAS Number 96-48-0
Deleted CAS Number 187997-16-6
FEMA Number 3291
Flavis Number 10.006
ECHA Number 202-509-5
FDA UNII OL659KIY4X
Nikkaji Number J3.971C
Beilstein Number 0105248
MDL MFCD00005386
COE Number 615
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 219 4-hydroxybutyric acid lactone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 96-48-0 ; 4-HYDROXYBUTANOIC ACID LACTONE
Synonyms
  • agrisynth BLO
  • 1,2-butanolide
  • 1,4-butanolide
  • 4-butanolide
  • butyro-1,4-lactone
  • 1,4-butyrolactone
  • 4-butyrolactone
  • g- butyrolactone
  • butyrolactone gamma
  • gamma- butyrolactone natural
  • butyryl lactone
  • 4-deoxytetronic acid
  • dihydro-2(3H)-furanone
  • 4,5-dihydro-2(3H)-furanone
  • dihydrofuran-2(3H)-one
  • furan-2(3H)-one, dihydro-
  • 2(3H)- furanone, dihydro-
  • 4-hydroxy-butanoic acid g-lactone
  • 4-hydroxybutanoic acid lactone
  • gamma- hydroxybutyric acid cyclic ester
  • 4-hydroxybutyric acid lactone
  • g- hydroxybutyric acid lactone
  • gamma- hydroxybutyric acid lactone
  • gamma- hydroxybutyrolactone
  • oxolan-2-one
  • 2-oxolanone
  • tetrahydro-2-furanone
  • 2,3,4,5-tetrahydro-2-furanone
  • 2(3H)-Furanone, dihydro-
  • NIH 10540
  • γ-BL
  • Butyrolactone
  • 1,4-Butanolide
  • γ-Butyrolactone
  • 4-Hydroxybutanoic acid lactone
  • γ-Hydroxybutyric acid lactone
  • Butanoic acid, 4-hydroxy-, γ-lactone
  • Butyric acid lactone
  • 4-Hydroxybutyric acid lactone
  • 4-Butanolide
  • 4-Deoxytetronic acid
  • 1-Oxacyclopentan-2-one
  • 2-Oxotetrahydrofuran
  • γ-Butyryllactone
  • 4,5-Dihydro-2(3H)-furanone
  • γ-Butalactone
  • 2-Oxolanone
  • 2,3,4,5-Tetrahydro-2-furanone
  • Paint Clean G
  • NSC 4592
  • GBL
  • LBG 11785
  • B 0767
  • 1,4-Butyrolactone

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

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Literature & References

oxolan-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:96-48-0
Pubchem (cid):7302
Pubchem (sid):134972536
Flavornet:96-48-0
Pherobase:View
Publications by PubMed
Chemical composition and aroma evaluation of essential oils from Evolvulus alsinoides L.
Catabolic pathway of gamma-caprolactone in the biocontrol agent Rhodococcus erythropolis.
Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans.
Inverse gas chromatographic evaluation of the influence of soy protein on the binding of selected butter flavor compounds in a wheat soda cracker system.
Nine new and five known polyketides derived from a deep sea-sourced Aspergillus sp. 16-02-1.
Determination of lactones in wines by headspace solid-phase microextraction and gas chromatography coupled with mass spectrometry.
Chemical composition and aroma evaluation of essential oils from Evolvulus alsinoides L.
Streptogramins - two are better than one!
Accelerated aging against conventional storage: effects on the volatile composition of chardonnay white wines.
Impact of perceptive interactions on red wine fruity aroma.
Comparative study of equimolar doses of gamma-hydroxybutyrate (GHB), 1,4-butanediol (1,4-BD) and gamma-butyrolactone (GBL) on catalepsy after acute and chronic administration.
Rapid and facile detection of four date rape drugs in different beverages utilizing proton transfer reaction mass spectrometry (PTR-MS).
Catabolic pathway of gamma-caprolactone in the biocontrol agent Rhodococcus erythropolis.
The discriminative stimulus effects of midazolam are resistant to modulation by morphine, amphetamine, dizocilpine, and γ-butyrolactone in rhesus monkeys.
Use of microfungi in the treatment of oak chips: possible effects on wine.
Role of roasting conditions in the profile of volatile flavor chemicals formed from coffee beans.
Behavioral effects of gamma-hydroxybutyrate, its precursor gamma-butyrolactone, and GABA(B) receptor agonists: time course and differential antagonism by the GABA(B) receptor antagonist 3-aminopropyl(diethoxymethyl)phosphinic acid (CGP35348).
Enzymology of the polyenes pimaricin and candicidin biosynthesis.
Behavioral effects and pharmacokinetics of gamma-hydroxybutyrate (GHB) precursors gamma-butyrolactone (GBL) and 1,4-butanediol (1,4-BD) in baboons.
Production of fermentation aroma compounds by Saccharomyces cerevisiae wine yeasts: effects of yeast assimilable nitrogen on two model strains.
Characterization of the most odor-active volatiles of orange wine made from a Turkish cv. Kozan (Citrus sinensis L. Osbeck).
In vivo functions of the gamma-butyrolactone autoregulator receptor in Streptomyces ambofaciens producing spiramycin.
Influence of wine turbidity on the accumulation of volatile compounds from the oak barrel.
Inverse gas chromatographic evaluation of the influence of soy protein on the binding of selected butter flavor compounds in a wheat soda cracker system.
GHB free acid: II. Isolation and spectroscopic characterization for forensic analysis.
Changes in the concentration of yeast-derived volatile compounds of red wine during malolactic fermentation with four commercial starter cultures of Oenococcus oeni.
Cloning and in vivo functional analysis by disruption of a gene encoding the gamma-butyrolactone autoregulator receptor from Streptomyces natalensis.
Discriminative stimulus effects of gamma-hydroxybutyrate (GHB) and its metabolic precursor, gamma-butyrolactone (GBL) in rats.
Off-vine grape drying effect on volatile compounds and aromatic series in must from Pedro Ximénez grape variety.
Influence of reinforcer type and route of administration on gamma-hydroxybutyrate discrimination in rats.
Effects of gamma-hydroxybutyrate (GHB) on schedule-controlled responding in rats: role of GHB and GABAB receptors.
The role of GABAB receptors in the discriminative stimulus effects of gamma-hydroxybutyrate in rats: time course and antagonism studies.
C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity.
Volatile compounds emitted by sclerotia of Sclerotinia minor, Sclerotinia sclerotiorum, and Sclerotium rolfsii.
Evolution of the aroma profile of sherry wine vinegars during an experimental aging in wood.
Varietal differentiation of red wines in the Valencian region (Spain).
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol: a case report and review of the literature.
Antioxidant properties of aroma compounds isolated from soybeans and mung beans.
Volatile compounds produced from monosodium glutamate in common food cooking.
Coma and respiratory depression following the ingestion of GHB and its precursors: three cases.
Direct release of the allergen tulipalin A from Alstroemeria cut flowers: a possible source of airborne contact dermatitis?
Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography.
Adverse events associated with ingestion of gamma-butyrolactone--Minnesota, New Mexico, and Texas, 1998-1999.
Endogenous digoxin-like activity of mammalian-lignans and their derivatives.
Gamma-butyrolactone's discriminability and effect on low rates of lever pressing by rats: alone and in combination with D-amphetamine and naloxone.
Native American food and medicinal plants. 3. alpha-Methylene butyrolactone from Erythronium grandiflorum Pursh.
Absorption of gamma-butyrolactone-gamma-carbonyl-L-histidyl-L-prolinamide citrate (DN-1417), an analog of thyrotropin-releasing hormone, in rats and dogs.
[Anaphylactic shock to celery and sensitization to ragweed and mugwort. Crossed or concomitant allergy?].
Dopamine analog-induced hyperglycemia in rats: involvement of the adrenal medulla and the endocrine pancreas.
Gamma-butyrolactone increases the rate of punished lever pressing by rats.
The effect of chronic ethanol administration on central neurotransmitter mechanisms.
[The cancerogenic activity of gamma-butyrolactone in mice].

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
CHEBI:View
CHEMBL:View
UM BBD:Search
KEGG (GenomeNet):C01770
HMDB (The Human Metabolome Database):HMDB00549
FooDB:FDB003392
Export Tariff Code:2932.29.6000
MedlinePlusSupp:View
Typical G.C.
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
Formulations/Preparations:
•electronic-grade butyrolactone is about 99% pure . •grade: technical

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 86.090217590332
Specific gravity @ 25 °C
Pounds per Gallon 9.32 to 9.403
Refractive Index 1.43 to 1.44 @ 20 °C
Boiling Point 204 to 205°C @ 760 mm Hg
Vapor Pressure 0.45 mmHg @ 25 °C
Vapor Density 3
Flash Point TCC Value 98.33 °C TCC
logP (o/w) -0.64
Solubility
alcohol Yes
water, 1.00E+06 mg/L @ 25 °C (exp) Yes

Organoleptic Properties

Odor Type: Creamy
creamy, oily, fatty, caramellic
General comment At 100.00 %. creamy oily fatty caramel
Mosciano, Gerard P&F 16, No. 2, 49, (1991) Creamy, oily with fatty nuances
Flavor Type: Milky
milky, creamy, fruity, peach
Mosciano, Gerard P&F 16, No. 2, 49, (1991) At 75.00 ppm. Milky, creamy with fruity peach-like afternotes

Occurrences

Potential Uses

Applications
Odor purposes Butterscotch, Coconut, Mango, Peach
Other purposes Solvents
Cosmetic purposes Fragrance, Solvents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36 - Irritating to eyes.
R 41 - Risk of serious damage to eyes.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/39 - Wear suitable clothing 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:
oral-rat LD50 1540 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(1), Pg. 49, 1987.

gavage-mouse LD50 1245 mg/kg
(Schafer & Bowles, 1985)

intraperitoneal-rat LD50 1000 mg/kg
BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.

oral-mouse LD50 1460 mg/kg
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: GENERAL ANESTHETIC
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 64(2), Pg. 3, 1999.

intraperitoneal-mouse LD50 1100 mg/kg
BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.

parenteral-mouse LDLo 1600 mg/kg
"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 687, 1955.

intravenous-rabbit LDLo 500 mg/kg
Archivum Immunologiae et Therapiae Experimentalis. Vol. 13, Pg. 70, 1965.

Dermal Toxicity:
skin-guinea pig LD50 > 5000 mg/kg
GAF Material Safety Data Sheet.

Inhalation Toxicity:
inhalation-rat LC50 > 5100 mg/m3/4H
National Technical Information Service. Vol. OTS0534527

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-butyrolactone usage levels up to:
0.5000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 110.00 (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: 5
Click here to view publication 5
average usual ppmaverage maximum ppm
baked goods: -20.00000
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: -20.00000
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: -10.00000
gelatins / puddings: --
granulated sugar: --
gravies: -10.00000
hard candy: -10.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -10.00000
milk products: -10.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: -10.00000
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

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to 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 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones evaluated by EFSA in FGE.10Rev1 (2009)
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
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):96-48-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7302
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
oxolan-2-one
Chemidplus:0000096480
EPA/NOAA CAMEO:hazardous materials
RTECS:96-48-0