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Merck
CN

20740

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
EC Number:
202-509-5
UNSPSC Code:
12352100
PubChem Substance ID:
329752019
Beilstein/REAXYS Number:
105248
MDL number:
MFCD00005386
Assay:
≥99.0% (GC)
Form:
liquid

Key Documents

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InChI key

YEJRWHAVMIAJKC-UHFFFAOYSA-N

InChI

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

SMILES string

O=C1CCCO1

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 %

refractive index

n20/D 1.437

bp

204-205 °C (lit.)

mp

−45 °C (lit.)

density

1.12 g/mL at 25 °C (lit.)

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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

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

208.4 °F - closed cup

flash_point_c

98 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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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
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
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
Axel Bidon-Chanal et al.
European journal of medicinal chemistry, 60, 479-489 (2013-01-29)
Glycogen synthase kinase 3β (GSK-3β) is widely recognised as a relevant player in the pathogenesis of several highly prevalent disorders such as Alzheimer's disease, mood disorders, diabetes and cancer. Therefore, this enzyme constitutes a highly attractive therapeutic target for the
Jagan N Thupari et al.
Proceedings of the National Academy of Sciences of the United States of America, 99(14), 9498-9502 (2002-06-13)
C75, a known inhibitor of fatty acid synthase is postulated to cause significant weight loss through decreased hypothalamic neuropeptide Y (NPY) production. Peripherally, C75, an alpha-methylene-gamma-butyrolactone, reduces adipose tissue and fatty liver, despite high levels of malonyl-CoA. To investigate this
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