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03-5330

Sigma-Aldrich

γ-Butyrolactone

SAJ first grade, ≥99.5%

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/REAXYS Number:
105248
MDL number:
MFCD00005386
UNSPSC Code:
12352005
PubChem Substance ID:
329747730

grade

SAJ first grade

vapor density

3 (vs air)

vapor pressure

1.5 mmHg ( 20 °C)

assay

≥99.5%

autoignition temp.

851 °F

expl. lim.

16 %

availability

available only in Japan

refractive index

n20/D 1.436 (lit.)

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.

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_germany

WGK 1

flash_point_f

208.4 °F - closed cup

flash_point_c

98 °C - closed cup

Certificates of Analysis (COA)

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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
Michael Seitz et al.
Current opinion in chemical biology, 9(3), 285-292 (2005-06-09)
Natural products containing a gamma-butyrolactone ring are abundant in nature; however, few general synthetic approaches to their stereoselective synthesis with broad structural variety are known. In this article, recent developments towards mono- and polycyclic gamma-butyrolactone natural products and analogs are
Long Wang et al.
Chemical communications (Cambridge, England), 49(33), 3458-3460 (2013-03-20)
Highly functionalized spiro[γ-butyrolactone-pyrrolidin-3,3'-oxindole] tricyclic skeletons were delivered successfully with high optical purity using an effective yet simple procedure.
Monica Blichowski et al.
Epilepsia, 56(7), 1081-1087 (2015-06-03)
Infantile spasms (or IS) is a catastrophic childhood epilepsy that is particularly prevalent in children with Down syndrome. Previously, we have shown that the Ts65Dn (Ts) mouse model of Down syndrome is a useful substrate upon which to develop an
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
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