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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:
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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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