gamma-butyrolactone

4-hydroxybutyric acid lactone

CAS: 96-48-0 C4 H6 O2 MW: 86.09022000 creamy milky

Identification

Namegamma-butyrolactone
IUPACoxolan-2-one
CAS Number96-48-0
EINECS202-509-5
FDA UNIIOL659KIY4X
Molecular FormulaC4 H6 O2
Molecular Weight86.09022000
MDL NumberMFCD00005386
Nikkaji NumberJ3.971C
Beilstein0105248
CoE Number615
XlogP3-0.60 (est)

Regulatory

JECFA Food Flavoring219 4-hydroxybutyric acid lactone
DG SANTE Food Flavourings10.006 butyro-1,4-lactone
FEMA Number3291
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)96-48-0 ; 4-HYDROXYBUTANOIC ACID LACTONE

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 98.00 to 100.00
Food Chemicals Codex Listed Yes
Specific Gravity 1.12000 to 1.13000 @ 25.00 °C.
Pounds per Gallon - (est). 9.320 to 9.403
Refractive Index 1.43000 to 1.44000 @ 20.00 °C.
Melting Point -43.30 °C. @ 760.00 mm Hg
Boiling Point 204.00 to 205.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.450000 mmHg @ 25.00 °C.
Vapor Density 3.00 ( Air = 1 )
Flash Point 209.00 °F. TCC ( 98.33 °C. )
logP (o/w) -0.640
Soluble in alcohol

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesfragrance

Organoleptic Properties

Odor Description
at 100.00 %.
Creamy, oily with fatty nuances
SWEET, AROMATIC, CREAMY
OILY, CREAMY, FATTY
Caramel, Fatty, Creamy
SWEET, AROMATIC, CREAMY
Taste Description at 75.00 ppm.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 1540 mg/kg
Dermal Toxicityskin-guinea pig LD50 > 5000 mg/kg
Inhalation Toxicityinhalation-rat LC50 > 5100 mg/m3/4H

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION\nBEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)\nBEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for gamma-butyrolactone usage levels up to0.5000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU)110.00 (μg/capita/day)
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
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-

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Prodasynth

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Potential Uses

FR butterscotch FR coconut FR mango FR peach solvents

Natural Occurrence

beer PMC bilberry fruit juice coffee PbMd PMC guava fruit headspace reunion @ 7.60% Data lavender oil spike spain @ 0.067% Data mango fruit pepper bell pepper fruit pineapple fruit wine orange wine PMC wine white wine PMC

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