Butyrolactone

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 Search

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

Title	Date	PubMed
The cin quorum sensing locus of Rhizobium etli CNPAF512 affects growth and symbiotic nitrogen fixation.	2002-01-04	11677232
Conformationally constrained analogues of diacylglycerol. 18. The incorporation of a hydroxamate moiety into diacylglycerol-lactones reduces lipophilicity and helps discriminate between sn-1 and sn-2 binding modes to protein kinase C (PK-C). Implications for isozyme specificity.	2001-12-06	11728178
Drug use and sexual risk behavior among gay and bisexual men who attend circuit parties: a venue-based comparison.	2001-12-01	11707675
Bovine oocytes treated prior to in vitro maturation with a combination of butyrolactone I and roscovitine at low doses maintain a normal developmental capacity.	2001-12	11746969
Cytotoxic butanolides from the stem bark of Formosan Lindera communis.	2001-12	11745027
A fast and simple GC MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related Plant species.	2001-12	11745025
Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana.	2001-12	11745023
Pentobarbital for severe gamma-butyrolactone withdrawal.	2001-12	11719746
Halogenated furanones from the red alga, Delisea pulchra, inhibit carbapenem antibiotic synthesis and exoenzyme virulence factor production in the phytopathogen Erwinia carotovora.	2001-11-27	11728727
Cyberpharmacies and the role of the US Food And Drug Administration.	2001-11-27	11720945
Pleiotropic functions of a Streptomyces pristinaespiralis autoregulator receptor in development, antibiotic biosynthesis, and expression of a superoxide dismutase.	2001-11-23	11557748
A synthetic approach to the Stemona alkaloids.	2001-11-16	11701032
Green tea epigallocatechin gallate: a natural inhibitor of fatty-acid synthase.	2001-11-16	11700039
10-Demethoxystegane, a new lignan from Steganotaenia araliacea.	2001-11	11720541
The chemical interconversion of GHB and GBL: forensic issues and implications.	2001-11	11714141
Hypothermia reduces the rate of dissociation of specific ligands from dopamine-D2 and 5-hydroxytryptamine1A receptors in the mouse brain in vivo.	2001-11	11692232
New diterpene from Hedychium villosum.	2001-11	11677028
Evidence for co-release of noradrenaline and dopamine from noradrenergic neurons in the cerebral cortex.	2001-11	11673793
GC-MS determination of gamma-hydroxybutyric acid (GHB) in blood.	2001-10-15	11587864
Detection, purification and characterisation of quorum-sensing signal molecules in plant-associated bacteria.	2001-10-04	11566391
Application of a convenient extraction procedure to analyze gamma-hydroxybutyric acid in fatalities involving gamma-hydroxybutyric acid, gamma-butyrolactone, and 1,4-butanediol.	2001-10	11599603
New sesquiterpene lactones from Elephantopus mollis and their leishmanicidal activities.	2001-10	11582544
Nuclear accumulation of cyclin B1 in mouse two-cell embryos is controlled by the activation of Cdc2.	2001-10	11566743
Factors influencing the cultivability of lake water bacteria.	2001-10	11566226
[GHB--dangerous, addictive and uncontrollable "party drug"].	2001-09-19	11602959
A novel three-component butenolide synthesis.	2001-09-06	11529779
Detection of gamma-butyrolactone (GBL) as a natural component in wine.	2001-09	11569560
A complex role for the gamma-butyrolactone SCB1 in regulating antibiotic production in Streptomyces coelicolor A3(2).	2001-09	11555283
Transgenic plants producing the bacterial pheromone N-acyl-homoserine lactone exhibit enhanced resistance to the bacterial phytopathogen Erwinia carotovora.	2001-09	11551068
High reactivity of alkyl sulfides towards epoxides under conditions of collagen fixation--a convenient approach to 2-amino-4-butyrolactones.	2001-09	11516082
Total synthesis of (-)-stemospironine.	2001-08-23	11506618
Stereocontrolled construction of tetrahydrofurans and gamma-butyrolactones using organomolybdenum chemistry.	2001-08-23	11506604
3-Phenyl-5-acyloxymethyl-2H,5H-furan-2-ones: synthesis and biological activity of a novel group of potential antifungal drugs.	2001-08-16	11495582
Enantioselective synthesis of ancepsenolide and its analogs.	2001-08	11577741
Disruption of a gene encoding a putative gamma-butyrolactone-binding protein in Streptomyces tendae affects nikkomycin production.	2001-08	11549012
Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds.	2001-08	11534761
Quorum-sensing in Gram-negative bacteria.	2001-08	11524130
Effects of high-affinity GABAB receptor antagonists on active and passive avoidance responding in rodents with gamma-hydroxybutyrolactone-induced absence syndrome.	2001-08	11512048
Coronin from roots of Annona muricata, a putative intermediate in acetogenin biosynthesis (1).	2001-08	11509986
Gamma-hydroxybutyrate, gamma-butyrolactone, and 1,4-butanediol.	2001-08	11493842
Haemodynamic effects of the bacterial quorum sensing signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone, in conscious, normal and endotoxaemic rats.	2001-08	11487515
Lack of the burst firing of thalamocortical relay neurons and resistance to absence seizures in mice lacking alpha(1G) T-type Ca(2+) channels.	2001-07-19	11498049
Cedarmycins A and B, new antimicrobial antibiotics from Streptomyces sp. TP-A0456.	2001-07	11560375
A simple procedure for synthesis of roxindole, a dopamine D2-receptor agonist.	2001-07	11512277
Pharmaceutically relevant metabolites from lichens.	2001-07	11499952
The LuxS family of bacterial autoinducers: biosynthesis of a novel quorum-sensing signal molecule.	2001-07	11489131
Involvement of catalytic amino acid residues in enzyme-catalyzed polymerization for the synthesis of polyesters.	2001	11749218
Bacterial response to siderophore and quorum-sensing chemical signals in the seawater microbial community.	2001	11716787
Regulation of gene expression by cell-to-cell communication: acyl-homoserine lactone quorum sensing.	2001	11700290
Quorum sensing in bacteria.	2001	11544353

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:23 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:23 GMT 2025`
Record UNII	OL659KIY4X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Butyrolactone

Official Name

English

GAMMA-BUTYROLACTONE

Preferred 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

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

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

Systematic Name

English

GAMMA-BUTYROLACTONE [FCC]

Common Name

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-.gamma.-Butyrolactone