66735
α-Methylene-γ-butyrolactone
purum, ≥97.0% (GC)
Synonym(s):
alpha-Methylene-gamma-butyrolactone, 3-Methylenedihydro-2(3H)-furanone, Tulipane
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About This Item
Empirical Formula (Hill Notation):
C5H6O2
CAS Number:
Molecular Weight:
98.10
PubChem Substance ID:
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
107939
MDL number:
grade
purum
assay
≥97.0% (GC)
contains
~1% 2,6-di-tert-butyl-4-methylphenol as stabilizer
refractive index
n20/D 1.472
bp
86-88 °C/12 mmHg (lit.)
density
1.119 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
C=C1CCOC1=O
InChI
1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChI key
GSLDEZOOOSBFGP-UHFFFAOYSA-N
Application
Very reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest
signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1
Storage Class
3 - Flammable liquids
flash_point_f
98.6 °F - closed cup
flash_point_c
37 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Francesca Cateni et al.
European journal of medicinal chemistry, 41(2), 192-200 (2005-12-22)
The synthesis of a series of alpha-methylene-gamma-butyrolactones (compounds 4a, 4b, 6-12, 16, 17) and alpha,beta-unsaturated-delta-lactones (compounds 19-23, 25, 26) starting from 4,4-dimethyldihydrofuran-2,3-dione (1) has been described. Their chemical structures were assigned by spectroscopic evidence. These new compounds exhibited significantly different
Sébastien Fuchs et al.
Photochemistry and photobiology, 86(3), 545-552 (2010-02-02)
(+) and (-) alpha-methylene-hexahydrobenzofuranone derivatives with a stereochemically pure cis ring junction were used as models of sesquiterpene lactones to study their photoreactivity toward thymidine. After 313 nm irradiation of a deoxygenated acetone solution of lactone models and thymidine, six
E Rozas-Muñoz et al.
Actas dermo-sifiliograficas, 103(6), 456-477 (2012-01-06)
Allergic contact dermatitis due to plants is common. Potentially allergenic plants and plant products are found in many everyday environments, such as the home, the garden, the workplace, and recreational settings. By improving our knowledge of allergenic plant-derived chemical compounds