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Chemical compound
γ-Butyrolactone (GBL) or gamma-butyrolactone is an organic compound with the formula O=CO(CH2)3. It is a hygroscopic, colorless, water-miscible liquid
Γ-Butyrolactone
Index of chemical compounds with the same name
Butyrolactone may refer to: beta-Butyrolactone gamma-Butyrolactone (GBL) This set index article lists chemical compounds articles associated with the same
Butyrolactone
Chemical compound
β-Butyrolactone is the intramolecular carboxylic acid ester (lactone) of the optically active 3-hydroxybutanoic acid. It is produced during chemical synthesis
Β-Butyrolactone
One of four stable isomers of butanediol
In organic chemistry, 1,4-butanediol is used for the synthesis of γ-butyrolactone (GBL). In the presence of phosphoric acid and high temperature, it dehydrates
1,4-Butanediol
Cyclic carboxylic ester
(spironolactone, mevalonolactone), enzymes (lactonase), neurotransmitters (butyrolactone, avermectins), antibiotics (macrolides like erythromycin; amphotericin
Lactone
Alcoholic drink made from fermented cereal grains
presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation". Comptes Rendus de l'Académie
Beer
Index of chemical compounds with the same molecular formula
acid Crotonic acid Isocrotonic acid 1,4-Butynediol Butyrolactones β-Butyrolactone γ-Butyrolactone Diacetyl, or butanedione Diepoxybutane 1,4-Dioxene Formyl
C4H6O2
compounds with the formula cyclo-O=COCHRCH2CH2. The parent member is γ-butyrolactone (R = H). A commercially important set of γ-lactones are derived from
Γ-Lactone
Chemical compound
preferred specimen for routine drug abuse monitoring purposes. Both γ-butyrolactone (GBL) and 1,4-butanediol are converted to GHB in the body. A method
Γ-Hydroxybutyric_acid
Chemical compound
γ-Octanolide; γ-Butyl-γ-butyrolactone; γ-Butylbutyrolactone; 4-Butyl-γ-butyrolactone; 5-Butyltetrahydro-2-furanone; γ-n-Butyl-γ-butyrolactone; Octanoic acid,
Γ-Octalactone
Recreational drug
banning the benzylpiperazine class of drugs in December 2009. gamma-Butyrolactone (GBL), another previously "legal high", was also banned in August 2009
Mephedrone
Chemical compound
penicillic acid, pulvinic acids, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid. In organic synthesis, it is used as a precursor
Tetronic_acid
Chemical compound
γ-Valerolactone (GVL) acts as a prodrug to GHV, analogously to how γ-butyrolactone (GBL) is a prodrug to GHB. 1,4-Butanediol (1-4-BD) Aceburic acid Valerenic
Γ-Hydroxyvaleric_acid
American baseball player (born 1969)
renewed. In November 2005, Rose was indicted for distributing gamma-Butyrolactone (GBL) to his Lookouts teammates in the late 1990s. GBL is known to be
Pete_Rose_Jr.
Chemical compound
Tulipalin A, also known as α-methylene-γ-butyrolactone, is a naturally occurring compound found in certain flowers such as tulips and alstroemerias. Tulipalin
Tulipalin_A
Epoxy-based polymer
polymerisation of the material. SU-8 series photoresists use gamma-butyrolactone or cyclopentanone as the primary solvent. SU-8 was originally developed
SU-8_photoresist
American basketball player
a "sleep aid" which included furanon di-hydro, also known as gamma butyrolactone, or GBL. He was talking to his wife on his phone while on the team bus
Tom_Gugliotta
Use of drugs with the primary intention to alter the state of consciousness
hydrate diethyl ether ethchlorvynol (Placidyl; "jelly-bellies") gamma-butyrolactone (GBL, a prodrug to GHB) gamma-hydroxybutyrate (GHB; G; Xyrem; "Liquid
Recreational_drug_use
Class of chemical compounds
Growth of a [CH3NH3]PbI3 single crystal in gamma-butyrolactone at 110 °C. The yellow color originates from the lead(II) iodide precursor.
Methylammonium_lead_halide
Chemical compound
industrially by a typical ester-to-amide conversion, by treating gamma-butyrolactone with methylamine. Alternative routes include the partial hydrogenation
N-Methyl-2-pyrrolidone
Heat-resistant high explosive
heat-resistant high explosive. It is slightly soluble (0.1 - 5 g/100 mL) in butyrolactone, DMF, DMSO, and N-methylpyrrolidone. It is produced by oxidizing trinitrotoluene
Hexanitrostilbene
Chemical compound
2-Acetylbutyrolactone (ABL) is a derivative of γ-butyrolactone that is used as a precursor in organic synthesis, and it is used to identify primary amines
2-Acetylbutyrolactone
Species of flowering plant
constituents.[citation needed] Seeds contain arctigenin, arctiin, and butyrolactone lignans. The burdock could be confused with rhubarb, the leaves of which
Arctium_lappa
Category of drug
ether, sevoflurane) 1,4-Butanediol Baclofen GABA Gabamide GABOB gamma-Butyrolactone (GBL) gamma-Hydroxybutyric acid (GHB) gamma-Hydroxyvaleric acid (GHV)
GABA_receptor_agonist
methamphetamine, amphetamine Nitroethane methamphetamine, amphetamine Gamma butyrolactone (other names include: GBL; dihydro-2(3H)-furanone; 1,2-butanolide; 1
DEA_list_of_chemicals
Genus of plants
tulips and are responsible for allergies. Tulipalin A, or α-methylene-γ-butyrolactone, is a common allergen, generated by hydrolysis of the glucoside tuliposide
Tulip
Chemical compound
economy. Recently, a method to use it to directly and simply produce Γ-Butyrolactone with electrolytic catalysts was developed. Furfural is carcinogenic
Furfural
"beta-propiolactone". scentsandflavors.com. Retrieved 14 June 2026. "gamma-butyrolactone". scentsandflavors.com. Retrieved 14 June 2026. "delta-gluconolactone"
List_of_esters
Chemical compound
Formation of 5-hydroxymethyldihydrofuranone [(S) - (+) - 4-hydroxymethyl-γ-butyrolactone]
Dihydrolevoglucosenone
Chemical compound
hexafluoroisopropanol (HFIP). The AlCl3-catalyzed acylation of benzene with γ-butyrolactone produces 1-tetralone. 1-Tetralone can be reduced via a Birch reduction
1-Tetralone
Species of fungus
species was first described in 1955. It has been reported to produce a butyrolactone and terrequinone A. A. ambiguus has been cultivated on both Czapek yeast
Aspergillus_ambiguus
Chemical compound
effects.[citation needed] It is synthesised by the reaction of gamma-butyrolactone and ethyl acetate with sodium ethoxide. 1,4-Butanediol (1,4-BD) 1,6-Dioxecane-2
Ethyl_acetoxy_butanoate
Classification of agents that are possibly carcinogenic to humans
1-Butyl glycidyl ether Butyl methacrylate Butylated hydroxyanisole β-Butyrolactone Caffeic acid Carbazole Carbon black Carbon nanotubes, multi-walled MWCNT-7
IARC_group_2B
Tisane made from dandelion root
dihydroconiferin, syringin, and dihydrosyringin Taraxacoside(an acylated gamma-butyrolactone glycoside) Lactupircin Carotenoids Lutein Violaxanthin Coumarins Esculin
Dandelion_coffee
Medication used to treat glaucoma and dry mouth
by chloroform. It can also be synthesized from 2-ethyl-3-carboxy-2-butyrolactone in an eight-step process from the acyl chloride (by treatment with thionyl
Pilocarpine
High-capacity electrochemical capacitor
acetonitrile, propylene carbonate, tetrahydrofuran, diethyl carbonate, γ-butyrolactone and solutions with quaternary ammonium salts or alkyl ammonium salts
Supercapacitor
Topics referred to by the same term
Boy Light, a Japan-exclusive Nintendo handheld Gamit language gamma-Butyrolactone Garden-based learning Glenn A. Black Laboratory of Archaeology, at Indiana
GBL
4-diamino-6-hydroxypyrimidine 56–06–4 C4H6O2 1,4-Butynediol C4H6O2 gamma-Butyrolactone C4H6O2 crotonic acid 3724–65–0 C4H6O2 diacetyl C4H6O2 diepoxybutane
Glossary_of_chemical_formulae
Type of fast-acting adhesive
chloride. Another viable solvent for removing cured cyanoacrylate is gamma-butyrolactone. Commercial debonders are also available, many based on propylene carbonate
Cyanoacrylate
Species of fungus
Japan. It has been reported to produce aspulvinone, asterriquinone, butyrolactones, citreoviridin, mevinolin, terrain, and terrequinone A. A. neoafricanus
Aspergillus_neoafricanus
Wafer bonding technique
component UV-sensitive negative photoresist based on epoxy resin, gamma butyrolactone, and triaryl sulfonium salt. SU-8 polymerizes at approximately 100 °C
Adhesive bonding of semiconductor wafers
Adhesive_bonding_of_semiconductor_wafers
Chemical compound
produced industrially almost exclusively by treating aqueous gamma-butyrolactone with ammonia at a temperature of 250–290 °C and pressures ranging from
2-Pyrrolidone
Incapacitating agent that may be used to commit rape
spray ingredient oxymetazoline; and certain GABAergics like GHB. Gamma-Butyrolactone is also often referred to as being used in sexual assaults. Researchers
Date_rape_drug
Chemical compound
Taraxacoside is an acylated γ-butyrolactone glycoside with the molecular formula C18H22O10 which has been isolated from roots of the plant Taraxacum officinale
Taraxacoside
Biological process that produces ethanol and carbon dioxide as by-products
presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation". Comptes Rendus de l'Académie
Ethanol_fermentation
Act of the Parliament of the United Kingdom
Flurazepam Dalmane, Staurodorm Gabapentin Neurontin Gabapentinoid 2019 gamma-Butyrolactone GBL sedative 2009 Metabolised to GHB in the body. Classified in December
Misuse_of_Drugs_Act_1971
Non-rechargeable battery using lithium metal as anode
tetrafluoroborate in propylene carbonate, dimethoxyethane, or gamma-butyrolactone 3 V 3.1 V 360–500 1,000 Cathode material formed by high-temperature
Lithium_metal_battery
Drugs that lower neurotransmission levels, reducing brain activity
Ethyl acetoxy butanoate (EAB) Aceburic acid (GHB acetate) gamma-Butyrolactone, γ-Butyrolactone (GBL) 2-Furanone, γ-crotonolactone (GCL) Gamma-Hydroxybutyraldehyde
Depressant
Chemical compound
Other names 5-Hydroxy-5H-furan-2-one, 2-Hydroxyfuranone-(5), β-oxo-γ-butyrolactone, 4-Oxobut-2-enoic acid, 2,5-dihydrofuran-2-one, beta-Formylacrylic acid
5-Hydroxy-2(5H)-furanone
Intense feelings of well-being
receptor agonists) (e.g., GHBTooltip γ-hydroxybutyrate, GBLTooltip γ-butyrolactone, 1,4-BDTooltip 1,4-butanediol) AMPA receptor antagonists (e.g., perampanel)
Euphoria
Chemical compound
described as a "γ-hydroxybutyric acid (GHB)-like agent" and a "potent y-butyrolactone-like sedative", but it shows no affinity for the GABAB receptor (GABABR)
HA-966
Overview of the events of the development of lithium-ion battery
lithium tetrafluoroborate (LiBF4) dissolved in a mixture of PC, gamma-butyrolactone (γBL) and ethylene carbonate (EC), as the electrolyte. The fluorinated
History of the lithium-ion battery
History_of_the_lithium-ion_battery
Chemical compound
which a six-membered benzene ring is annulated with a five-membered γ-butyrolactone ring. The 2(3H)-benzofuranone can also be considered as a lactone of
2-Coumaranone
Cyclic compound (C2H4O)
compounds containing active methylene group leads to the formation of butyrolactones: Ethylene oxide enters into the Friedel–Crafts reaction with benzene
Ethylene_oxide
Pharmaceutical compound
hypersomnia drugs 1,4-Butanediol (1,4-BD) 1,6-Dioxecane-2,7-dione γ-Butyrolactone (GBL) Aceburic acid Ethyl acetoxy butanoate Glyceryl-tris-3-hydroxybutyrate
1,2,3-Tris(4-hydroxybutyroyloxy)propane
1,2,3-Tris(4-hydroxybutyroyloxy)propane
Simplified chemical analog of amitriptyline
the active ingredients in Ketogan) and SKF-89976A. Amitriptyline γ-Butyrolactone Bölcskei H, Tarnawa I, Kocsis P (June 2008). "Voltage-gated sodium channel
DPH-362
Chemical compound
encephalopathy. Glutaric acid can be prepared by the ring-opening of butyrolactone with potassium cyanide to give the potassium salt of the carboxylate-nitrile
Glutaric_acid
Dicarboxylic acid
By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020". Grand View Research
Succinic_acid
n-Butyl acrylate Butylated hydroxytoluene (BHT) Butyl benzyl phthalate γ-Butyrolactone Caffeine Cantharidin Caprolactam Captan Carbaryl 3-Carbethoxypsoralen
IARC_group_3
ISBN 9780470199046. Priepke, Henning; Weigand, Stefan; Brückner, Reinhard (2006). "A Butyrolactone → 1,3-Diol Strategy for the Obtention of Tolypothrix Polyethers – Stereoselective
Narasaka–Prasad_reduction
Species of fungus
pulmonary aspergillosis. It has been reported to produce aszonalenine, butyrolactones, citrinin, and gregatins. A. niveus has been cultivated on both Czapek
Aspergillus_niveus
Chemical compound
gamma-hydroxybutyric acid (GHB). 1,4-Butanediol (1,4-BD) 1,6-Dioxecane-2,7-dione γ-Butyrolactone (GBL) γ-Hydroxybutyraldehyde (GHBAL) γ-Valerolactone (GVL) Aceturic
Aceburic_acid
Canadian federal drug regulation act
3-benzodioxole) and any essential oil containing more than 4% safrole Gamma-butyrolactone (dihydro-2(3H)-furanone) 1,4-butanediol Red Phosphorus White Phosphorus
Controlled Drugs and Substances Act
Controlled_Drugs_and_Substances_Act
Chemical compound
curable polymers applied as inks, coatings or adhesives. Starting from γ-Butyrolactone, 2-pyrrolidone is synthesized by treatment with ammonia. Subsequently
N-Vinylpyrrolidone
Species of flowering plant
because little research has been done. It is known to contain α-methylene butyrolactone. The plant is emetic, emollient, and antiscorbutic when fresh.[medical
Erythronium_albidum
Type of medication
(GHB) prodrugs are known. These include 1,4-butanediol (1,4-BD) and γ-butyrolactone (GBL), as well as the metabolic intermediate γ-hydroxybutyraldehyde
Neurotransmitter_prodrug
Potent opioid used in euthanasia
2-ethyl-2-(3-methoxyphenyl)butan-1-amine (3). Amide formation via reaction with gamma-butyrolactone (GBL) completes the synthesis of embutramide (4). Elks J (14 November
Embutramide
Chemical compound
comparative study of human and animal sensitivity to alpha-methylene-gamma-butyrolactone and derivatives". The British Journal of Dermatology. 99 (2): 163–9
Helenin
Chemical compound
co-solvent. δ-Valerolactone Valeric acid 1,4-Butanediol (1,4-BD) γ-Butyrolactone (GBL) NIH National Toxicology Program Baird, Zachariah Steven; Uusi-Kyyny
Γ-Valerolactone
Species of fungus
1962. It has been reported to produce asperphenamate, atrovenetins, butyrolactones, citrinin, and gregatins. A. allahabadii has been cultivated on both
Aspergillus_allahabadii
GHB receptor coding gene in the species Homo sapiens
(SR-95531) NCS-382 1,4-Butanediol - metabolised into GHB by ADH and ALDH γ-Butyrolactone (GBL) – metabolised into GHB by paraoxonase γ-Valerolactone (GVL) –
GHB_receptor
Organic compound with formula (CH2CO)2
alkylating agent, and unlike analogue β-lactones propiolactone and β-butyrolactone, diketene is inactive as a carcinogen, possibly due to the instability
Diketene
Species of fungus
first described in 2011. It has been reported to produce aszonalenin, butyrolactones, citrinin, a decaturin, dihydrocitrinone, an isocoumarin, and serantrypinone
Aspergillus_floccosus
Species of bacterium
Ipposhi, H; Okamoto, S; Nakano, H; Nihira, T; Yamada, Y (November 1997). "Butyrolactone autoregulator receptor protein (BarA) as a transcriptional regulator
Streptomyces_virginiae
Galactose Gangalioside Gamma globulin Gamma-aminobutyric acid Gamma-butyrolactone Gamma-hydroxybutyrate (GHB) Gastrin Gelatin Geraniol Ghrelin Globulin
List_of_biomolecules
Investigational antibiotic
and Enterococcus faecium. They also do not have the α-methylene-γ-butyrolactone pharmacophore of methylenomycin A and C, implying they have a different
Premethylenomycin_C_lactone
Chemical compound
the structure of helenalin has two reactive groups (α-methylene-γ-butyrolactone and a cyclopentenone group) that can undergo a Michael addition. The
Helenalin
Chemical reaction
heterocyclic fluorides, although ring opening has been observed for γ-butyrolactone. The six-membered lactide does not experience ring opening. Fluorination
Fluorination by sulfur tetrafluoride
Fluorination_by_sulfur_tetrafluoride
of an α,ω-diol with 2,2-diethoxytetrahydrofuran (synthesized from γ-butyrolactone and triethylorthoformate). In polycondensation small molecules are formed
Polyorthoester
Chemical compound
Akira Suzuk (1998). "Synthesis of 4-(2-Bromo-2-Propenyl)-4-Methyl-Y-Butyrolactone by the Reaction of Ethyl Levulinate with (2-Bromoallyl)Diisopropoxyborane
Diisopropyl_ether
Chemical compound
hydrogenated. Diethyl maleate can similarly be hydrogenated to either butyrolactone or 1,4-butanediol, depending on conditions. Sebacoin, derived from the
Copper_chromite
Chemical compound
3-Tris(4-hydroxybutyroyloxy)propane Aceburic acid Ethyl acetoxy butanoate gamma-Butyrolactone gamma-Hydroxybutyraldehyde Hanioka Y. Resin composition and resin molded
1,6-Dioxecane-2,7-dione
Type of capacitor
solvents, such as dimethylformamide (DMF), dimethylacetamide (DMA), or γ-butyrolactone (GBL). These capacitors with organic solvent electrolytes are suitable
Aluminum electrolytic capacitor
Aluminum_electrolytic_capacitor
Azerbaijani chemist (1857–1921)
University of Strasbourg, Khanlarov defended his thesis entitled "On Butyrolactones and Ethylbutyrolactones" and received a doctorate in chemistry. This
Movsum_bey_Khanlarov
University of Santo Tomas Stereoslective routes to aryl-substituted y-butyrolactones and their applications towards the synthesis of highly oxidised furanocembranoids
National Academy of Science and Technology Awards
National_Academy_of_Science_and_Technology_Awards
412: 2-alkyl-3-oxoalkanoate reductase EC 1.1.1.413: A-factor type γ-butyrolactone 1′-reductase (1S-forming) EC 1.1.1.414: L-galactonate 5-dehydrogenase
List_of_EC_numbers_(EC_1)
Section of the United States Controlled Substances Act
controlled substance in schedule I or II. (B) The designation of gamma butyrolactone or any other chemical as a listed chemical pursuant to paragraph (34)
Federal_Analogue_Act
American teen who died after being dosed with date-rape drug GHB
which they had added either gamma-hydroxybutyric acid (GHB) or gamma-butyrolactone (GBL). Melanie stated that her face became numb soon afterward, and
Death_of_Samantha_Reid
Chemical compound
molecule was introduced to a strong base the desired α-methylene-γ-butyrolactone group was formed. A Makaiyama aldol condensation with
Xanthatin
Chemical compound
G. Rodewald (1983). "Substituted γ-butyrolactones From Carboxylic Acids And Olefins: γ-(n-octyl)-γ-butyrolactone". Org. Synth. 61: 22. doi:10.15227/orgsyn
Manganese(III)_acetate
Chemical compound
H. Ogawa, S. Wakabayashi (1986), "Facile synthesis of 2-methylene-4-butyrolactones", Chem. Lett., vol. 15, no. 4, pp. 541–544, doi:10.1246/cl.1986.541{{citation}}:
Itaconic_anhydride
Transition metal carbene complex
Brunsvold, William R. (December 1975). "Synthesis of α-methylene-γ-butyrolactone via transition metal carbene complexes". Journal of Organometallic Chemistry
Fischer_carbene
Pharmaceutical compound
each side of the molecule, allowing it to form a homopolymer. Its γ-butyrolactone ring is involved in most of its biological functions. The unsaturated
Cynaropicrin
Oxyacid of phosphorus
amine oxide. Oxidation of THF with peroxymonophosphoric acid gives γ-butyrolactone. Schmidlin, Julius; Massini, Paul (1910). "Phosphormonopersäure und
Peroxymonophosphoric_acid
Chemical compound
derived from D-3,4-dihydroxybutanoic acid, by using 3-hydroxy-gamma-butyrolactone as a chiral synthon It is used as one of the monomers for manufacture
1,2,4-Butanetriol
Monomers which increase in volume
epoxide with a lactone: The epoxide cyclohexene oxide and the lactone γ-butyrolactone are reacting to the spiro orthoester spiro-7-9-dioxacyclo[4.3.0]nonane-8
Expanding_monomer
Norwood was banned from competition after testing positive for Gamma-Butyrolactone at the 1986 World Modern Pentathlon Championships. During her two and
Lori_Norwood
Chemicals regulated in the United States
25013-16-5 Butyl benzyl phthalate (BBP) Developmental 85-68-7 beta-Butyrolactone Cancer 3068-88-0 July 1, 1987 Cacodylic acid Cancer 75-60-5 Cadmium
California Proposition 65 list of chemicals
California_Proposition_65_list_of_chemicals
Chemical compound
Other names (αR,βR)-α,β-Bis(4-hydroxy-3-methoxybenzyl)butyrolactone Identifiers CAS Number 580-72-3 Y 3D model (JSmol) Interactive image
Matairesinol
British author and broadcaster
the University of Sussex – died after taking the 'legal high' gamma butyrolactone (GBL). She was 21 years old. Stewart placed her women's health work
Maryon_Stewart
travel, tourism, insurance
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