117757
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:
Molecular Weight:
100.12
Beilstein/REAXYS Number:
80418
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.
Application
α-Methyl-γ-butyrolactone was used as model compound in Bracketing experiments to investigate the thermodynamically favored site of reaction of pilocarpine.
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
163.4 °F - closed cup
flash_point_c
73 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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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)
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