591-81-1

Basic information

• Product Name: Gamma-butyrolactone(GBL)
• Synonyms: Gamma-butyrolactone(GBL);4-Hydroxybutanoate;4-Hydroxybutyric;4-hydroxy-butanoic acid;4-HYDROXYBUTYRATE;GAMMA-HYDROXYBUTYRICACID;C00989;g-Hydroxybutyrate
• CAS NO: 591-81-1
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 103.09658
• Mol File: 591-81-1.mol
• Article Data: 40

Chemical Properties

• Melting Point: 212℃
• Boiling Point: 235.97°C (rough estimate)
• Flash Point: 146.8 °C
• Appearance: /
• Density: 1.1405 g/cm3
• Vapor Pressure: 0.000156mmHg at 25°C
• Refractive Index: 1.4761 (estimate)
• PKA: 4.72(at 25℃)
• CAS DataBase Reference: Gamma-butyrolactone(GBL)(CAS DataBase Reference)
• NIST Chemistry Reference: Gamma-butyrolactone(GBL)(591-81-1)
• EPA Substance Registry System: Gamma-butyrolactone(GBL)(591-81-1)

Safety Data

• Hazardous Substances Data: 591-81-1(Hazardous Substances Data)

Usage

Description

γ-Hydroxybutyric acid (GHB), also known as 4- hydroxybutanoic acid, is a naturally occurring substance found in the human central nervous system, as well as in wine, beef, small citrus fruits, and almost all animals in small amounts. It is also categorized as an illegal drug in many countries. It is currently regulated in Australia and New Zealand, Canada, most of Europe and in the US. GHB as the sodium salt, known as sodium oxybate (INN) or by the trade name Xyrem, is used to treat cataplexy and excessive daytime sleepiness in patients with narcolepsy.

Uses

Anesthetic (intravenous). In treatment of narcolepsy; in treatment of alcoholism. This is a Schedule III controlled substance.

Definition

ChEBI: 4-Hydroxybutyric acid is a 4-hydroxy monocarboxylic acid that is butyric acid in which one of the hydrogens at position 4 is replaced by a hydroxy group.

Pharmacokinetics

4-Hydroxybutyric Acid (GHB) is found in all human tissues, with the highest concentration in the brain. This agent stimulates the GHB receptor, and to a lesser extent GABA-B receptors. Although, the precise function and metabolic pathways of GHB are not fully understood, this agent easily crosses the blood-brain barrier, and affects the activities and levels of dopamine, acetylcholine, dynorphin and serotonin. The primary effect of GHB is central nervous system depression, thereby, its main usage is to induce anesthesia.

Clinical Use

The only common medical applications for GHB today are in the treatment of narcolepsy and more rarely alcoholism. GHB is the active ingredient in the prescription medication sodium oxybate (Xyrem). Sodium oxybate is approved by the U.S. Food and Drug Administration (FDA) for the treatment of cataplexy associated with narcolepsy and Excessive Daytime Sleepiness (EDS) associated with narcolepsy.

Metabolic pathway

Also note that both of the metabolic breakdown pathways shown for GHB can run in either direction, depending on the concentrations of the substances involved, so the body can make its own GHB either from GABA or from succinic semialdehyde. Under normal physiological conditions, the concentration of GHB in the body is rather low, and the pathways would run in the reverse direction to what is shown here to produce endogenous GHB. However, when GHB is consumed for recreational or health promotion purposes, its concentration in the body is much higher than normal, which changes the enzyme kinetics so that these pathways operate to metabolise GHB rather than producing it.

InChI:InChI=1/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 6303-58-8 4-phenyloxybutanoic acid 
• 627-00-9 γ-chlorobutyric acid 
• 2623-87-2 bromobutyric acid 
• 70160-04-2 4-isopentyloxy-butyric acid 
• 543-20-4 succinoyl dichloride 
• 151-50-8 potassium cyanide 
• 627-18-9 1-bromo-3-propanol 
• 107-92-6 butyric acid 
• 147-85-3 L-proline 
• 56-86-0 L-glutamic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 1191-95-3 cyclobutanone 
• 9004-34-6 cellulose 

Downstream Products

• 96-48-0 4-butanolide 
• 89399-39-3 4-phosphonooxy-butyric acid 
• 55133-95-4 C₁₀H₂₄O₃Si₂ 
• 168642-00-0 4-<4'-Oxa-(2,2':6',2''-terpyridinyl)>butanoic acid 
• 110-63-4 Butane-1,4-diol 
• 91970-62-6 benzyl 4-hydroxybutanoate 
• 110-15-6 succinic acid 
• 86864-59-7 5-((tert-butyldimethylsilyl)oxy)pentan-2-one 
• 92813-35-9 9-(3-hydroxyropropyl)acridine 
• 1464148-99-9 C₁₉H₃₀O₃ 
• 692-29-5 Succinic semialdehyde 
• 26976-72-7 4-acetoxybutyric acid 
• 2403-66-9 2-(3-hydroxypropyl)benzimidazole 
• 403730-22-3 4-[(4,4'-Dimethoxytrityl)oxy]butyric acid, triethylammonium salt 

Relevant articles and documents

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Nicotinamide Adenine Dinucleotide-Dependent Redox-Neutral Convergent Cascade for Lactonizations with Type II Flavin-Containing Monooxygenase

A nicotinamide adenine dinucleotide (NADH)-dependent redox-neutral convergent cascade composed of a recently discovered type II flavin-containing monooxygenase (FMO?E) and horse liver alcohol dehydrogenase (HLADH) has been established. Two model reaction cascades were analyzed for the synthesis of γ-butyrolactone and chiral bicyclic lactones. In the former cascade, all substrates were converted into one single product γ-butyrolactone with high atom efficiency. More than 130 mM γ-butyrolactone were obtained when applying 100 mM cyclobutanone and 50 mM 1,4-butanediol in this cascade. In the second cascade where bicyclo[4.2.0]octan-7-one and cis-1,2-cyclohexanedimethanol were coupled, the ketone substrate was converted to the corresponding normal lactone with an ee value of 89–74% (3aS, 7aS) by FMO?E alone and the abnormal lactone with an ee value of >99% (3aR, 7aS) was formed by both HLADH and FMO?E. (Figure presented.).

Di-(benzimidazole)-1, 2, 3-triazole derivative as well as preparation and application thereof in inflammatory dermatosis

The invention belongs to the technical field of drug small molecules, and particularly discloses a brand-new di-(benzimidazole)-1, 2, 3-triazole derivative as well as preparation and application of the brand-new di-(benzimidazole)-1, 2, 3-triazole derivative. The research finds that the brand new compound has an excellent drug effect and low toxic and side effects on the aspect of inflammatory dermatosis, and has a good application prospect in the aspect of drug development of the inflammatory dermatosis.

Characterization of carboxylic acid reductases for biocatalytic synthesis of industrial chemicals

Carboxylic acid reductases (CARs) catalyze the reduction of a broad range of carboxylic acids into aldehydes, which can serve as common biosynthetic precursors to many industrial chemicals. This work presents the systematic biochemical characterization of five carboxylic acid reductases from different microorganisms, including two known and three new ones, by using a panel of short-chain dicarboxylic acids and hydroxy acids, which are common cellular metabolites. All enzymes displayed broad substrate specificities. Higher catalytic efficiencies were observed when the carbon chain length, either of the dicarboxylates or of the terminal hydroxy acids, was increased from C2 to C6. In addition, when substrates of the same carbon chain length are compared, carboxylic acid reductases favor hydroxy acids over dicarboxylates as their substrates. Whole-cell bioconversions of eleven carboxylic acid substrates into the corresponding alcohols were investigated by coupling the CAR activity with that of an aldehyde reductase in Escherichia coli hosts. Alcohol products were obtained in yields ranging from 0.5 % to 71 %. The de novo stereospecific biosynthesis of propane-1,2-diol enantiomer was successfully demonstrated with use of CARs as the key pathway enzymes. E. coli strains accumulated 7.0 mm (R)-1,2-PDO (1.0 % yield) or 9.6 mm (S)-1,2-PDO (1.4 % yield) from glucose. This study consolidates carboxylic acid reductases as promising enzymes for sustainable synthesis of industrial chemicals.