226416
α-Methylene-γ-butyrolactone
97%
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
107939
Assay:
97%
Form:
liquid
Quality Level
assay
97%
form
liquid
contains
~2% 2,6-di-tert-butyl-p-cresol as stabilizer
refractive index
n20/D 1.472 (lit.)
bp
86-88 °C/12 mmHg (lit.)
solubility
water: soluble(lit.)
density
1.119 g/mL at 25 °C (lit.)
functional group
ester
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
α-Methylene-γ-butyrolactone (Tulipane) was used to develop optically active spiro-[butyrolactone-pyrrolidine] via Cu(I)-catalyzed exo-selective 1,3-dipolar cycloaddition of azomethine ylides.
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
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Qing-Hua Li et al.
Chemical communications (Cambridge, England), 49(83), 9642-9644 (2013-09-12)
An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98 : 2), excellent enantioselectivity (96->99% ee) and a broad substrate scope under mild conditions.
Fernando Torres et al.
Cancer letters, 269(1), 139-147 (2008-06-03)
In this study, we investigated the effect of three synthetic alpha-methylene-gamma-butyrolactones (MBL) on viability of 10 human tumor cell lines and found that these lactones were highly cytotoxic against leukemia cells. Studies performed on HL-60 cells indicate that MBL induce
Jean-Pierre Lepoittevin et al.
Chemical record (New York, N.Y.), 9(5), 258-270 (2009-11-26)
Natural products containing an alpha-methylene-gamma-butyrolactone moiety, mainly of the sesquiterpene type, are widely observed in plants, which upon coming into contact with skin, will induce major skin toxicological side effects or phytodermatitis. Indeed two main dermatological pathologies have been associated