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66735

Sigma-Aldrich

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:
547-65-9
Molecular Weight:
98.10
Beilstein:
107939
MDL number:
MFCD00005407
UNSPSC Code:
12352100
PubChem Substance ID:
24884906

grade

purum

Assay

≥97.0% (GC)

contains

~1% 2,6-di-tert-butyl-4-methylphenol as stabilizer

refractive index

n20/D 1.472 (lit.)
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

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Application

Very reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H317,H412

Hazard Classifications

Aquatic Chronic 3 - Flam. Liq. 3 - Skin Sens. 1

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

98.6 °F - closed cup

Flash Point(C)

37 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Mickaël Jean et al.
Organic letters, 7(13), 2663-2665 (2005-06-17)
[reaction: see text] A polyamine derivative was prepared from alpha-methylene-gamma-butyrolactone. This method used Michael addition and lactone aminolysis followed by the nucleophilic substitution of the hydroxyl group by an azido group. The coupling of a lipophilic alkyne led to a
T Patrick Montgomery et al.
Journal of the American Chemical Society, 134(27), 11100-11103 (2012-06-28)
Upon exposure of acrylic ester 1 to alcohols 2a-i in the presence of a cyclometalated iridium catalyst modified by (-)-TMBTP, catalytic C-C coupling occurs, providing enantiomerically enriched 5-substituted α-exo-methylene γ-butyrolactones 3a-i. Bromination of the methylene butyrolactone products followed by zinc-mediated
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
Javier A Menendez et al.
Drug news & perspectives, 18(6), 375-385 (2005-10-26)
Fatty acid synthase (FAS)-catalyzed de novo fatty acid biosynthesis, an anabolic energy-storage pathway largely considered of minor importance in humans, actively contributes to the cancer phenotype by virtue of its ability to specifically regulate the expression and activity of Her-2/neu
Taiji Nomura et al.
Plant physiology, 159(2), 565-578 (2012-04-05)
Tuliposides, the glucose esters of 4-hydroxy-2-methylenebutanoate and 3,4-dihydroxy-2-methylenebutanoate, are major secondary metabolites in tulip (Tulipa gesneriana). Their lactonized aglycons, tulipalins, function as defensive chemicals due to their biological activities. We recently found that tuliposide-converting enzyme (TCE) purified from tulip bulbs
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