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HomeProduct name listTulipalin A

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: 2024-11-18 21:14:07
Tulipalin A Structural

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)
ghs
Flame
Flammables
GHS02
ghs
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.

Computed Descriptors for Tulipalin A

InChIKey GSLDEZOOOSBFGP-UHFFFAOYSA-N

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