U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H6O2
Molecular Weight 86.0892
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYROLACTONE

SMILES

O=C1CCCO1

InChI

InChIKey=YEJRWHAVMIAJKC-UHFFFAOYSA-N
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2

HIDE SMILES / InChI

Molecular Formula C4H6O2
Molecular Weight 86.0892
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Water-soluble L-alanine and related oligopeptide conjugates with poly[(R,S)-3-hydroxybutanoic acid] oligomers, synthesis and structural studies by means of electrospray ionization multistage mass spectrometry.
2001
Acylated homoserine lactone detection in Pseudomonas aeruginosa biofilms by radiolabel assay.
2001
Synthesis of multiple N-acylhomoserine lactones is wide-spread among the members of the Burkholderia cepacia complex.
2001 Apr
Fingertip dermatitis in a retail florist.
2001 Apr
A Cdk5-p35 stable complex is involved in the beta-amyloid-induced deregulation of Cdk5 activity in hippocampal neurons.
2001 Apr 1
Enantioselective synthesis of ancepsenolide and its analogs.
2001 Aug
Quorum-sensing in Gram-negative bacteria.
2001 Aug
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.
2001 Aug
Haemodynamic effects of the bacterial quorum sensing signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone, in conscious, normal and endotoxaemic rats.
2001 Aug
Synthesis of beta-lactones by the regioselective, cobalt and Lewis acid catalyzed carbonylation of simple and functionalized epoxides.
2001 Aug 10
Bovine oocytes treated prior to in vitro maturation with a combination of butyrolactone I and roscovitine at low doses maintain a normal developmental capacity.
2001 Dec
Cytotoxic butanolides from the stem bark of Formosan Lindera communis.
2001 Dec
A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species.
2001 Dec
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison.
2001 Dec 1
More on gamma-butyrolactone (GBL/GHB) toxicity.
2001 Feb
Total synthesis of natural dysidiolide.
2001 Feb 23
Comparison of direct and indirect methods of measuring the precursors of beta-methyl-gamma-octalactone and their application to the analysis of Sessile oak wood.
2001 Jan 5
Cedarmycins A and B, new antimicrobial antibiotics from Streptomyces sp. TP-A0456.
2001 Jul
A case of withdrawal from the GHB precursors gamma-butyrolactone and 1,4-butanediol.
2001 Jul
Dual control of hydrogen cyanide biosynthesis by the global activator GacA in Pseudomonas aeruginosa PAO1.
2001 Jun 12
The languages of bacteria.
2001 Jun 15
Kinetics of the AHL regulatory system in a model biofilm system: how many bacteria constitute a "quorum"?
2001 Jun 8
Urinary phytoestrogens and postmenopausal breast cancer risk.
2001 Mar
Stereoselective synthesis of substituted gamma-butyrolactones by the [3+2] annulation of allylic silanes with chlorosulfonyl isocyanate: enantioselective total synthesis of (+)-blastmycine.
2001 Mar 8
Polo-like kinase 1 phosphorylates cyclin B1 and targets it to the nucleus during prophase.
2001 Mar 8
Analytical performance of luminescent immunoassays of different format for serum daidzein analysis.
2001 May
Hypothermia reduces the rate of dissociation of specific ligands from dopamine-D2 and 5-hydroxytryptamine1A receptors in the mouse brain in vivo.
2001 Nov
New diterpene from Hedychium villosum.
2001 Nov
Evidence for co-release of noradrenaline and dopamine from noradrenergic neurons in the cerebral cortex.
2001 Nov
Application of a convenient extraction procedure to analyze gamma-hydroxybutyric acid in fatalities involving gamma-hydroxybutyric acid, gamma-butyrolactone, and 1,4-butanediol.
2001 Oct
New sesquiterpene lactones from Elephantopus mollis and their leishmanicidal activities.
2001 Oct
Nuclear accumulation of cyclin B1 in mouse two-cell embryos is controlled by the activation of Cdc2.
2001 Oct
Factors influencing the cultivability of lake water bacteria.
2001 Oct
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.
2001 Oct 15
Detection, purification and characterisation of quorum-sensing signal molecules in plant-associated bacteria.
2001 Oct 4
Detection of gamma-butyrolactone (GBL) as a natural component in wine.
2001 Sep
High reactivity of alkyl sulfides towards epoxides under conditions of collagen fixation--a convenient approach to 2-amino-4-butyrolactones.
2001 Sep
[GHB--dangerous, addictive and uncontrollable "party drug"].
2001 Sep 19
Involvement of catalytic amino acid residues in enzyme-catalyzed polymerization for the synthesis of polyesters.
2001 Summer
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:22:06 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:06 GMT 2023
Record UNII
OL659KIY4X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTYROLACTONE
INCI   MI   VANDF   WHO-DD  
INCI  
Official Name English
.GAMMA.-BUTYROLACTONE [FHFI]
Common Name English
Revivarant
Common Name English
NIH 10540
Code English
GH Revitalizer
Common Name English
4-HYDROXYBUTANOIC ACID LACTONE
Common Name English
LBG 11785
Code English
4-BUTYROLACTONE
Common Name English
BUTYROLACTONE [INCI]
Common Name English
2(3H)-FURANONE, DIHYDRO-
Systematic Name English
Remforce
Common Name English
NSC-4592
Code English
Butyrolactone [WHO-DD]
Common Name English
Blue Nitro
Common Name English
GAMMA-BUTYROLACTONE
FCC   HSDB  
Systematic Name English
GBL
Common Name English
GAMMA-BUTYROLACTONE [IARC]
Common Name English
BUTYROLACTONE [VANDF]
Common Name English
FEMA NO. 3291
Code English
GAMMA-BUTYROLACTONE [HSDB]
Common Name English
BUTYROLACTONE [MI]
Common Name English
.GAMMA.-BUTYROLACTONE
FHFI  
Systematic Name English
GAMMA-BUTYROLACTONE [FCC]
Common Name English
Classification Tree Code System Code
WIKIPEDIA Designer-drugs-.gamma.-Butyrolactone
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
DEA NO. 2011
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
Code System Code Type Description
NSC
4592
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-509-5
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
EVMPD
SUB32501
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
HSDB
4290
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
JECFA MONOGRAPH
457
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
MERCK INDEX
m2870
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6020224
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
CHEBI
42639
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
SMS_ID
100000124564
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
WIKIPEDIA
GAMMA-BUTYROLACTONE
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
FDA UNII
OL659KIY4X
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
DRUG BANK
DB04699
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
CAS
96-48-0
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
PUBCHEM
7302
Created by admin on Fri Dec 15 15:22:06 GMT 2023 , Edited by admin on Fri Dec 15 15:22:06 GMT 2023
PRIMARY
Related Record Type Details
PARENT->PRECURSOR
GBL is typically marketed for sale as a cleaning solvent or polish. GBL is used as a GHB substitute and as a precursor for clandestine manufacturing of GHB.
Related Record Type Details
METABOLITE ACTIVE -> PARENT
GBL is readily converted into GHB by the body’s own natural process. Because of this, GBL has similarpharmacological effects to GHB.
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY
GBL is used as a GHB substitute and as a precursor for clandestine manufacturing of GHB.