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Merck
CN

20740

Sigma-Aldrich

γ-Butyrolactone

puriss., ≥99.0% (GC)

Synonym(s):

γ-Hydroxybutyric acid lactone, 4-Hydroxybutyric acid lactone, GBL

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About This Item

Empirical Formula (Hill Notation):
C4H6O2
CAS Number:
96-48-0
Molecular Weight:
86.09
Beilstein:
105248
EC Number:
202-509-5
MDL number:
MFCD00005386
UNSPSC Code:
12352100
PubChem Substance ID:
329752019

Key Documents

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vapor density

3 (vs air)

vapor pressure

1.5 mmHg ( 20 °C)

grade

puriss.

Assay

≥99.0% (GC)

form

liquid

autoignition temp.

851 °F

expl. lim.

16 %

drug control

Pszichotróp anyag / Psychotropic Substance (Hungary), 78/2022. (XII. 28.) BM rendelet

refractive index

n20/D 1.436 (lit.)
n20/D 1.437

bp

204-205 °C (lit.)

mp

−45 °C (lit.)

density

1.12 g/mL at 25 °C (lit.)

SMILES string

O=C1CCCO1

InChI

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

InChI key

YEJRWHAVMIAJKC-UHFFFAOYSA-N

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Biochem/physiol Actions

Precursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.
Precursor of γ-hydroxybutyric acid (GHB); blocks dopamine release.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318,H336

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

208.4 °F - closed cup

Flash Point(C)

98 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Tezcan Guney et al.
Organic letters, 15(3), 613-615 (2013-01-18)
The total synthesis of paracaseolide A, a valuable cell-cycle progression inhibitor, was accomplished in 8 steps from known compounds, with 6.6% overall yield. The synthetic strategy creates strong potential for diversification.
Christian Westendorf et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(10), 3853-3858 (2013-02-23)
The rapid reorganization of the actin cytoskeleton in response to external stimuli is an essential property of many motile eukaryotic cells. Here, we report evidence that the actin machinery of chemotactic Dictyostelium cells operates close to an oscillatory instability. When
Zheng-Yuan Su et al.
Chemical research in toxicology, 26(3), 477-485 (2013-02-28)
Cancer development has been linked to epigenetic modifications of cancer oncogenes and tumor suppressor genes; in advanced metastatic cancers, severe epigenetic modifications are present. We previously demonstrated that the progression of prostate tumors in TRAMP mice is associated with methylation
Michelle Wood et al.
Journal of chromatography. A, 1056(1-2), 83-90 (2004-12-15)
We have developed a rapid method that enables the simultaneous analysis of gamma-hydroxybutyrate (GHB) and its precursors, i.e. gamma-butyrolactone (GBL) and 1,4-butanediol (1,4-BD) in urine. The method comprised a simple dilution of the urine sample, followed by liquid chromatography-tandem mass
Bo Xue et al.
Biochemistry, 52(13), 2359-2370 (2013-03-07)
The in vitro evolution and engineering of quorum-quenching lactonases with enhanced reactivities was achieved using a thermostable GKL enzyme as a template, yielding the E101G/R230C GKL mutant with increased catalytic activity and a broadened substrate range [Chow, J. Y., Xue
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