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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

Key Documents

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Product Name

γ-Butyrolactone, puriss., ≥99.0% (GC)

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 %

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.)

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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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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
Géraldine Le Goff et al.
Journal of natural products, 76(2), 142-149 (2013-02-08)
Three novel hydrazides, geralcins C-E (1-3), were isolated from Streptomyces sp. LMA-545, together with MH-031 and geralcins A and B. This unusual family of compounds was isolated from liquid-state and agar-supported fermentation using Amberlite XAD-16 solid-phase extraction during the cultivation
Samuel K Kutty et al.
Journal of medicinal chemistry, 56(23), 9517-9529 (2013-11-07)
Fimbrolides from marine algae have shown promising activity against quorum sensing (QS), a chief regulatory and communication system in bacteria controlling biofilm formation and virulence factor. Nitric oxide (NO) at sublethal concentration has also been reported to induce dispersal of
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.
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
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