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Safety Information

226416

Sigma-Aldrich

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:
547-65-9
Molecular Weight:
98.10
Beilstein:
107939
MDL number:
MFCD00005407
UNSPSC Code:
12352100
PubChem Substance ID:
24853566
NACRES:
NA.22

Quality Level

200

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

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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.

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

226416-1ML:
226416-250MG:
226416-VAR:
226416-BULK:
226416-1G:4548174005163
226416-5G:4548174005170

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6710
BCCH7873
BCCG7008
BCCC9019
BCBZ5322

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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
Joëlle Moïse et al.
Organic letters, 9(9), 1695-1698 (2007-04-05)
[reaction: see text] Olefin cross-metathesis between alpha-methylene-gamma-butyrolactone and terminal olefins is described. Moderate to excellent yields of alpha-alkylidene-gamma-butyrolactones were obtained with high E-stereoselectivity in the presence of low catalyst loading in refluxing CH2Cl2. In addition, the use of various additives
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
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
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