Tulipalin A

Synonym(s):α′-Angelicalactone;3-Methylenedihydro-2(3H)-furanone;5-Methylenedihydro-2(3H)-furanone;alpha-Methylene-gamma-butyrolactone;Tulipane

CAS NO.：547-65-9
Empirical Formula: C5H6O2
Molecular Weight: 98.1
MDL number: MFCD00005407
EINECS: 208-931-6
SAFETY DATA SHEET (SDS)
Update Date: 2025-12-17 14:06:09

What is Tulipalin A?

Description

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.

Chemical properties

clear colourless to light yellow or slightly pink

The Uses of Tulipalin A

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

The Uses of Tulipalin A

Allergen in the Liliaeeae family of plants to whieh speeies such as Tulip, Alstromeria, Erythronium dens canis and americanum belong.

The Uses of Tulipalin A

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.

Definition

ChEBI: A butan-4-olide having a methylene group at the 3-position.

Contact allergens

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.

Properties of Tulipalin A

Melting point:	<25 °C
Boiling point:	86-88 °C12 mm Hg(lit.)
Density	1.119 g/mL at 25 °C(lit.)
refractive index	n20/D 1.472(lit.)
Flash point:	99 °F
storage temp.	2-8°C
solubility	water: soluble(lit.)
form	Liquid
color	Clear colorless to light yellow or slightly pink
Merck	14,6062
BRN	107939
CAS DataBase Reference	547-65-9(CAS DataBase Reference)
NIST Chemistry Reference	«alpha»-Methylene-«gamma»-butyrolactone(547-65-9)
EPA Substance Registry System	2(3H)-Furanone, dihydro-3-methylene- ( (547-65-9)

Safety information for Tulipalin A

Signal word	Warning
Pictogram(s)	Flame Flammables GHS02 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H226:Flammable liquids H317:Sensitisation, Skin H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.