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Gamma-Butyrolactone
Gamma-Butyrolactone
General
Systematic name Dihydrofuran-2(3H)-one
Other names GBL, butyrolactone, 1,4-lactone, 4-butyrolactone, 4-hydroxybutyric acid lactone, and gamma-hydroxybutyric acid lactone
Molecular formula C4H6O2
SMILES O=C1CCCO1
Molar mass 86.089 g/mol
Appearance Colorless liquid
CAS number [96-48-]
Properties
Density and phase 1.144 g/mL
Solubility in water Hygroscopic
Melting point -45 °C
Boiling point 204 - 205 °C
Acidity (pKa)  ?
Viscosity  ? cP at ?°C
Structure
Dipole moment  ? D
Hazards
MSDS External MSDS
Main hazards Harmful
NFPA 704
Flash point 98 °C (closed cup)
R/S statement R: R22 R36
S: S26 S36
RTECS number  ?
Related compounds
Related compounds  ?
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

gamma-Butyrolactone, also known as GBL, butyrolactone, 1,4-lactone, 4-butyrolactone, 4-hydroxybutyric acid lactone, and gamma-hydroxybutyric acid lactone, is a hygroscopic colorless oily liquid with a weak characteristic odor and moderate solubility in water (≥ 10 g / 100 ml). gamma-Butyrolactone is a common solvent and reagent in chemistry and is used as an aroma compound, as a stain remover, as a paint stripper, and as a gamma-hydroxybutyric acid (GHB) precursor and substitute. Image File history File links Download high resolution version (1026x718, 4 KB) Description: Chemical structure of gamma-Butyrolactone. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is defined as mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydronium ions from an acid. ... The related Category:Units of viscosity has been nominated for deletion, merging, or renaming. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... A hygroscopic substance is a substance that absorbs water readily from its surroundings. ... Odor receptors on the antennae of a Luna moth An odor or odour (see spelling differences) is a chemical dissolved in air, generally at a very low concentration, which we perceive by the sense of olfaction. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... A reagent or reactant is any substance used in a chemical reaction. ... This article or section includes a list of works cited but its sources remain unclear because it lacks in-text citations. ... An aroma compound, also known as odorant, aroma, fragrance, flavor, is a chemical compound that has a smell or odor. ... Paint stripper, or paint remover, is the generic name given to solvent mixtures designed to removed paint and clean the underlying surface. ... GHB redirects here. ...

Contents

Chemistry

gamma-Butyrolactone is a lactone. It is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. Under acidic conditions it forms an equilibrium mixture of both compounds. gamma-Butyrolactone can be synthesized from gamma-hydroxybutyric acid by removal of water or by distillation from such a mixture. It may also be obtained via oxidation of tetrahydrofuran (THF). One such process, which affords GBL in yields of up to 80%, utilises bromine generated in situ from an aqueous solution of sodium bromate and potassium hydrogen sulfate [1]. A lactone is a cyclic ester in organic chemistry. ... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... The common (Arrhenius) definition of a base is a chemical compound that either donates hydroxide ions or absorbs hydrogen ions when dissolved in water. ... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ... Dissolving table salt in water This article is about a chemical solution; for other uses of the term solution, see solution (disambiguation). ... General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ... A magnified crystal of a salt (halite/sodium chloride) Salt covering the floor of Bad Water in Death Valley, CA, the lowest point in the US. A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral... GHB redirects here. ... Chemical equilibrium is the state in which the concentrations of the reactants and products have no net change over time. ... For other uses of THF, see THF (disambiguation) Tetrahydrofuran is a heterocyclic organic compound. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... In situ is a Latin phrase meaning in the place. ... Sodium bromate is a strong oxidant, mainly used as printing and dyeing auxiliary, hair-permagent, chemical agent, or gold solvent in gold mines when used with sodium bromide. ...


A Natural Component In Wine

The compound gamma-butyrolactone (GBL) was found in extracts from samples of unadulterated wines. This finding indicates that GBL is a naturally occurring component in some wines and may be present in similar products. The concentration detected was approximately 5 microg/mL and was easily observed using a simple extraction technique followed by GC/MS analysis. These results illustrate the need to carefully examine an allegedly adulterated sample's matrix before determining a sample was laced with GBL.


Recreational use

GBL is a prodrug of GHB. Metabolism takes place in stomach and blood plasma. GBL is longer acting and has a shorter onset than GHB. Otherwise, effects are similar to GHB, although weight for weight it is significantly more powerful, meaning dosage must be lowered accordingly. If ingested undiluted through the oral route, GBL can irritate innards. It is possible for oral ingestion of GBL to cause nausea and other similar problems, possibly more so than with GHB. A prodrug is a pharmacological substance (drug) which is administered in an inactive (or significantly less active) form. ... Gamma-hydroxybutyrate (4-hydroxybutanoic acid, C4H8O3) is both a drug and a naturally occurring compound found in the mammalian brain, where it might function as a neurotransmitter. ...


Restricting the use of GBL

Although GBL is an unclassified drug in the United Kingdom, the risk to people's lives is being recognised on the London Gay Scene, where use is more prevalent than other parts of the country. Vauxhall, home to the majority of London's after-hours underground gay clubs, has witnessed an unprecedented number of collapses and death. At the end of 2006, a campaign began to reduce the number of people using GBL in the area. The effects of this campaign are yet to be seen.


Notes

  1. ^ Metsger, L.; Bittner, S. Autocatalytic Oxidation of Ethers with Sodium Bromate, Tetrahedron 2000, 56, 1905-1910

See also

  • gamma-Hydroxybutyrate (GHB)

GHB redirects here. ...

External links



 
 

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