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: 2026-02-02 18:10:39
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 | n |
| 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. |
Computed Descriptors for Tulipalin A
| InChIKey | GSLDEZOOOSBFGP-UHFFFAOYSA-N |
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