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117757

Sigma-Aldrich

α-Methyl-γ-butyrolactone

98%

Synonym(s):

4,5-Dihydro-3-methyl-2(3H)-furanone

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About This Item

Empirical Formula (Hill Notation):
C5H8O2
CAS Number:
1679-47-6
Molecular Weight:
100.12
Beilstein:
80418
EC Number:
216-846-0
MDL number:
MFCD00005396
UNSPSC Code:
12352100
PubChem Substance ID:
24847344
NACRES:
NA.22
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Quality Level

100

Assay

98%

refractive index

n20/D 1.432 (lit.)

bp

78-81 °C/10 mmHg (lit.)

solubility

THF: soluble

functional group

ester

SMILES string

CC1CCOC1=O

InChI

1S/C5H8O2/c1-4-2-3-7-5(4)6/h4H,2-3H2,1H3

InChI key

QGLBZNZGBLRJGS-UHFFFAOYSA-N

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General description

α-Methyl-γ-butyrolactone undergoes benzylation to give racemic α-benzyl-α-methyl-γ-butyrolactone[1].

Application

α-Methyl-γ-butyrolactone was used as model compound in Bracketing experiments to investigate the thermodynamically favored site of reaction of pilocarpine[2].

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

163.4 °F - closed cup

Flash Point(C)

73 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0257
STBK4808
STBK0473
STBH4176
STBF7296V

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M Satterfield et al.
Journal of the American Society for Mass Spectrometry, 10(3), 209-216 (1999-03-09)
Analysis of the sites of reaction of a biologically important compound, pilocarpine, a molecule with imidazole and butyrolactone rings connected by a methylene bridge, has been accomplished in a quadrupole ion trap with the aim of characterizing its structure/reactivity relationships.
Eric B Gonzales et al.
The Journal of pharmacology and experimental therapeutics, 309(2), 677-683 (2004-01-27)
Alkyl-substituted butyrolactones have both inhibitory and stimulatory effects on GABA(A) receptors. Lactones with small alkyl substitutions at the alpha-position positively modulate the channel, whereas beta-substituted lactones tend to inhibit the GABA(A) receptor. These compounds mediate inhibition through the picrotoxin site
Hagai Tavori et al.
Bioorganic & medicinal chemistry, 16(15), 7504-7509 (2008-06-24)
Paraoxonase1 (PON1) is a HDL bound enzyme and many of the anti-atherogenic properties of HDL are attributed to PON1. The enzyme precise mechanism of protective action and its endogenous substrate remain elusive. PON1 hydrolyzes organophosphates, arylesters and lactones, whereas the

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