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
Bacterial response to siderophore and quorum-sensing chemical signals in the seawater microbial community.
2001
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
Quorum sensing controls the synthesis of virulence factors by modulating rsmA gene expression in Erwinia carotovora subsp. carotovora.
2001 Apr
Fingertip dermatitis in a retail florist.
2001 Apr
Serum enterolactone and risk of breast cancer: a case-control study in eastern Finland.
2001 Apr
Disruption of a gene encoding a putative gamma-butyrolactone-binding protein in Streptomyces tendae affects nikkomycin production.
2001 Aug
Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds.
2001 Aug
Coronin from roots of Annona muricata, a putative intermediate in acetogenin biosynthesis (1).
2001 Aug
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.
2001 Aug
3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones: synthesis and biological activity of a novel group of potential antifungal drugs.
2001 Aug 16
Stereocontrolled construction of tetrahydrofurans and gamma-butyrolactones using organomolybdenum chemistry.
2001 Aug 23
Cytotoxic butanolides from the stem bark of Formosan Lindera communis.
2001 Dec
Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana.
2001 Dec
More on gamma-butyrolactone (GBL/GHB) toxicity.
2001 Feb
Novel glucocorticoid antedrugs possessing a 17beta-(gamma-lactone) ring.
2001 Feb 15
Total synthesis of natural dysidiolide.
2001 Feb 23
Increased fatty acid synthase is a therapeutic target in mesothelioma.
2001 Jan
Adverse events, including death, associated with the use of 1,4-butanediol.
2001 Jan 11
Gamma butyrolactone (GBL) withdrawal syndromes.
2001 Jan-Feb
The LuxS family of bacterial autoinducers: biosynthesis of a novel quorum-sensing signal molecule.
2001 Jul
In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol.
2001 Jul
IL-8 production in human lung fibroblasts and epithelial cells activated by the Pseudomonas autoinducer N-3-oxododecanoyl homoserine lactone is transcriptionally regulated by NF-kappa B and activator protein-2.
2001 Jul 1
Lack of the burst firing of thalamocortical relay neurons and resistance to absence seizures in mice lacking alpha(1G) T-type Ca(2+) channels.
2001 Jul 19
Gamma-butyrolactone synthesis via catalytic asymmetric cyclocarbonylation.
2001 Jul 4
Pseudomonas aeruginosa GacA, a factor in multihost virulence, is also essential for biofilm formation.
2001 Jun
The Circuit Party Men's Health Survey: findings and implications for gay and bisexual men.
2001 Jun
Development of a new reaction system for the synthesis of highly optically active alpha,gamma-substituted gamma-butyrolactones.
2001 Jun 1
Quenching quorum-sensing-dependent bacterial infection by an N-acyl homoserine lactonase.
2001 Jun 14
The languages of bacteria.
2001 Jun 15
Synthesis of (+/-)-bakkenolide-A and its C-7, C-10, and C-7,10 epimers by means of an intramolecular Diels-Alder reaction.
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
Intracellular Ca(2+) mobilization and kinase activity during acylated homoserine lactone-dependent quorum sensing in Serratia liquefaciens.
2001 Mar 2
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
New phenolic constituents from the fruit juice of Phyllanthus emblica.
2001 May
Increased fatty acid synthase as a therapeutic target in androgen-independent prostate cancer progression.
2001 May 1
Synthesis and biological evaluation of purine-containing butenolides.
2001 May 24
A compartment model to calculate time-dependent concentration profiles of topically applied chemical compounds in the anterior compartments of the rabbit eye.
2001 May-Jun
10-Demethoxystegane, a new lignan from Steganotaenia araliacea.
2001 Nov
A synthetic approach to the Stemona alkaloids.
2001 Nov 16
Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase.
2001 Nov 16
Pleiotropic functions of a Streptomyces pristinaespiralis autoregulator receptor in development, antibiotic biosynthesis, and expression of a superoxide dismutase.
2001 Nov 23
Nuclear accumulation of cyclin B1 in mouse two-cell embryos is controlled by the activation of Cdc2.
2001 Oct
A complex role for the gamma-butyrolactone SCB1 in regulating antibiotic production in Streptomyces coelicolor A3(2).
2001 Sep
Transgenic plants producing the bacterial pheromone N-acyl-homoserine lactone exhibit enhanced resistance to the bacterial phytopathogen Erwinia carotovora.
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
The cin quorum sensing locus of Rhizobium etli CNPAF512 affects growth and symbiotic nitrogen fixation.
2002 Jan 4
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.