α-Methylen-γ-butyrolacton

Bezeichnung:α-Methylen-γ-butyrolacton

Englisch Name:Tulipalin A

CBNumberCB0290434

SummenformelC5H6O2

Molgewicht98.1

Synonyma

α-Methylen-γ-butyrolacton

α-Methylen-γ-butyrolacton physikalisch-chemischer Eigenschaften

Schmelzpunkt	<25 °C
Siedepunkt	86-88 °C12 mm Hg(lit.)
Dichte	1.119 g/mL at 25 °C(lit.)
Brechungsindex	n20/D 1.472(lit.)
Flammpunkt	99 °F
storage temp.	2-8°C
Löslichkeit	water: soluble(lit.)
Aggregatzustand	Liquid
Farbe	Clear colorless to light yellow or slightly pink
Merck	14,6062
BRN	107939
InChIKey	GSLDEZOOOSBFGP-UHFFFAOYSA-N
CAS Datenbank	547-65-9(CAS DataBase Reference)
NIST chemische Informationen	«alpha»-Methylene-«gamma»-butyrolactone(547-65-9)
EPA chemische Informationen	2(3H)-Furanone, dihydro-3-methylene- ( (547-65-9)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	42/43-52/53-10
S-Sätze:	23-36/37-61-45
RIDADR	1993
WGK Germany	3
RTECS-Nr.	LU3580400
F	1-8-10
HazardClass	3.2
PackingGroup	III
HS Code	29349990

Gefahreninformationscode (GHS)

R-Sätze Betriebsanweisung:
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Beschreibung
Tulipalin A is an unsubstituted -methylene-butyrolaetone eontained in the sap of tulips, Alstroemeria spp. (Peruvian lily) and Erythronium (dog tooth violet, fawn-lily). Tulipalin B seems to have a weak capacities to sensitize.
Chemische Eigenschaften
clear colourless to light yellow or slightly pink
Verwenden
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.
Verwenden
Very reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest
Verwenden
Allergen in the Liliaeeae family of plants to whieh speeies such as Tulip, Alstromeria, Erythronium dens canis and americanum belong.
Definition
ChEBI: A butan-4-olide having a methylene group at the 3-position.
Kontakt-Allergie
Tulipalin A is the unsubstituted a-methylene-g-butyrolactone contained in the sap of damaged tulips (Liliaceae family) and Alstroemeria (Alstroemeriaceae family). Tulipalin B, due to hydrolysis of tuliposide B, seems to have a weak sensitizing capacity.