ContaminantDB: Gamma-Butyrolactone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-05 03:12:29 UTC

Update Date

2026-03-26 21:07:39 UTC

Accession Number

CHEM002088

Identification

Common Name

Gamma-Butyrolactone

Class

Small Molecule

Description

One of the furans with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.

Contaminant Sources

DEA Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HPV EPA Chemicals
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Ether
Food Toxin
Household Toxin
Indicator and Reagent
Industrial/Workplace Toxin
Metabolite
Organic Compound
Solvent
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Butanolide	ChEBI
1,4-Butanolide	ChEBI
1,4-Lactone	ChEBI
4-Butyrolactone	ChEBI
4-Deoxytetronic acid	ChEBI
4-Hydroxybutyric acid lactone	ChEBI
Butyrolactone	ChEBI
Dihydro-2(3H)-furanone	ChEBI
gamma-Butanolactone	ChEBI
gamma-Hydroxybutyric acid lactone	ChEBI
gamma-Hydroxybutyrolactone	ChEBI
Tetrahydrofuran-2-one	ChEBI
4-Deoxytetronate	Generator
4-Hydroxybutyrate lactone	Generator
g-Butanolactone	Generator
Γ-butanolactone	Generator
g-Hydroxybutyrate lactone	Generator
g-Hydroxybutyric acid lactone	Generator
gamma-Hydroxybutyrate lactone	Generator
Γ-hydroxybutyrate lactone	Generator
Γ-hydroxybutyric acid lactone	Generator
g-Hydroxybutyrolactone	Generator
Γ-hydroxybutyrolactone	Generator
g-Butyrolactone	Generator
Γ-butyrolactone	Generator
1-Oxacyclopentan-2-one	HMDB
2,3,4,5-Tetrahydro-2-furanone	HMDB
2-Oxolanone	HMDB
2-Oxotetrahydrofuran	HMDB
4,5-Dihydro-2(3H)-furanone	HMDB
4-Butanolide	HMDB
4-Hydroxy-butanoate	HMDB
4-Hydroxy-butanoic acid	HMDB
4-Hydroxy-butanoic acid g-lactone	HMDB
4-Hydroxybutanoate	HMDB
4-Hydroxybutanoic acid	HMDB
4-Hydroxybutanoic acid lactone	HMDB
Butyric acid lactone	HMDB
g-Butalactone	HMDB
g-Butyryllactone	HMDB
gamma-Butalactone	HMDB
gamma-Butyryllactone	HMDB
GBL	HMDB
Paint clean g	HMDB
Tetrahydro-2-furanone	HMDB
4 Butyrolactone	HMDB
gamma Butyrolactone	HMDB
Furanone, tetrahydro 2	HMDB
1,4 Butanolide	HMDB
4 Hydroxybutyric acid lactone	HMDB
Lactone, 4-hydroxybutyric acid	HMDB
gamma-Butyrolactone	MeSH

Chemical Formula

C₄H₆O₂

Average Molecular Mass

86.089 g/mol

Monoisotopic Mass

86.037 g/mol

CAS Registry Number

96-48-0

IUPAC Name

oxolan-2-one

Traditional Name

butyrolactone

SMILES

O=C1CCCO1

InChI Identifier

InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2

InChI Key

YEJRWHAVMIAJKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

butan-4-olide (CHEBI:42639 )
Lactones (LMFA07040004 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Adipose Tissue
Neuron

Pathways

Not Available

Applications

Not Available

Biological Roles

neurotoxin

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless oily liquid (14).

Experimental Properties

Property	Value
Melting Point	-45°C
Boiling Point	Not Available
Solubility	1000.0 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	238 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	0.15	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.31 m³·mol⁻¹	ChemAxon
Polarizability	8.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9000000000-500445dc73cb69119e6b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-9000000000-d3df175d3315ed446e14	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9000000000-500445dc73cb69119e6b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-9000000000-d3df175d3315ed446e14	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-bd4b413f20907d13a107	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-4a6de93563809aa51a33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-4a6de93563809aa51a33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-b5163f6eb1e8004e61a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-004l-9000000000-1066d349a6023c66dd64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-002f-9000000000-d3df175d3315ed446e14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-507998514018a44c4cf0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9000000000-d4ec4947321dfb11fab4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b2a1436205f5365513b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-fb7c9ada825a0c62979f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-9000000000-95fda8a898d02f7e71ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9000000000-c8282365f175b61ca8c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-ec20127c74818b1f634d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9000000000-86d21b481322417edf81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-4f454124d6cece18a212	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-709821dd006aa045c8b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-ffe2d9473d85a58305c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a4219a074939d10a0f5f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004l-9000000000-2fc3f4165b5808b41e93	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (3) ; oral (3) ; injection (3) ; dermal (3).

Mechanism of Toxicity

Gamma-butyrolactone is rapidly converted to gamma-hydroxybutyrate. This may account for the subsequent central nervous system depressant. Gamma-butyrolactone is an anesthetic that causes a selective increase in brain dopamine by antagonizing transmitter release from nerve terminal. It is also an endogenous brain metabolite that may be derived from glutamate through gamma-aminobutyrate. GBL binds to the picrotoxin receptor (2, 1).

Metabolism

Gamma-Butyrolactone undergoes rapid and quantitative conversion by lactonases, yielding gamma-hydroxybutyric acid (4).

Toxicity Values

LD50: 17.2 mL/kg (Oral, Rat) (581)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (13)

Uses/Sources

Common solvent and reagent in chemistry and is used as an aroma compound, as a stain remover, as a superglue remover, as a paint stripper, and as a solvent in some wet aluminium electrolytic capacitors (14).

Minimum Risk Level

Not Available

Health Effects

CNS depression; amnesia and hypotonia. Rarely, hypertension, orthostatic hypotension, apnea, dyskinesias, dystonias, and hypomania occur.

Symptoms

Headache, confusion, ataxia, urinary incontinence or urgency, difficulty breathing, bradycardia, uncontrollable shaking, hallucinations, seizure-like activity (uncontrollable or unusual movements), and acidosis. Hypothermia has been reported in adults and children following exposure (15).

Treatment

In case of oral exposure, administer a benzodiazepine IV. There is no antidote. Treatment is symptomatic and supportive. (15)

Concentrations

Not Available

External Links

DrugBank ID

DB04699

HMDB ID

HMDB0000549

FooDB ID

FDB003392

Phenol Explorer ID

Not Available

KNApSAcK ID

C00053167

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

5533

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Fabio Giannessi, Maria Ornella Tinti, Francesco De Angelis, “Process for producing®-3-hydroxy-4-butyrolactone useful for preparing®-carnitine.” U.S. Patent US6127552, issued February, 1998.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12429914

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23245230

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24500753

4. Zhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang. Process for preparation of g-butyrolactone with high yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 13 pp.

5. Fukui Y, Matsusima E, Muramoto K, Nagai N, Ohama K, Yamashita K: Validation of a simple gas chromatographic-mass spectrometric method for the determination of gamma-butyrolactone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):73-80.

6. Thupari JN, Landree LE, Ronnett GV, Kuhajda FP: C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9498-502. Epub 2002 Jun 11.

7. Wood M, Laloup M, Samyn N, Morris MR, de Bruijn EA, Maes RA, Young MS, Maes V, De Boeck G: Simultaneous analysis of gamma-hydroxybutyric acid and its precursors in urine using liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2004 Nov 12;1056(1-2):83-90.

8. Quintanilla RA, Orellana DI, Gonzalez-Billault C, Maccioni RB: Interleukin-6 induces Alzheimer-type phosphorylation of tau protein by deregulating the cdk5/p35 pathway. Exp Cell Res. 2004 Apr 15;295(1):245-57.

9. Knust U, Hull WE, Spiegelhalder B, Bartsch H, Strowitzki T, Owen RW: Analysis of enterolignan glucuronides in serum and urine by HPLC-ESI-MS. Food Chem Toxicol. 2006 Jul;44(7):1038-49. Epub 2006 Feb 20.

10. Selmaoui B, Aymard N, Lambrozo J, Touitou Y: Evaluation of the nocturnal levels of urinary biogenic amines in men exposed overnight to 50-Hz magnetic field. Life Sci. 2003 Oct 31;73(24):3073-82.

11. Oshima I, Saito S, Shiota K, Miyake A, Oka Y, Nakayama R: Kinetic study on disappearance of gamma-butyrolactone-gamma-carbonyl-L-histidyl-L-prolinamide (DN-1417) from plasma using a radioimmunoassay for DN-1417 isobutylamide. J Pharmacobiodyn. 1983 Mar;6(3):202-8.

12. Yeatman DT, Reid K: A study of urinary endogenous gamma-hydroxybutyrate (GHB) levels. J Anal Toxicol. 2003 Jan-Feb;27(1):40-2.

13. Elliott S, Burgess V: The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages. Forensic Sci Int. 2005 Jul 16;151(2-3):289-92. doi: 10.1016/j.forsciint.2005.02.014.

Gamma-Butyrolactone (CHEM002088)

Structure for CHEM002088: Gamma-Butyrolactone