Tulipalin A Chemical Properties

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

Water Solubility 

water: soluble(lit.)

Merck 

14,6062

BRN 

107939

Cosmetics Ingredients Functions

SKIN PROTECTING

InChI

1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

InChIKey

GSLDEZOOOSBFGP-UHFFFAOYSA-N

SMILES

C=C1CCOC1=O

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

Hazard Codes 

Xn

Risk Statements 

42/43-52/53-10

Safety Statements 

23-36/37-61-45

RIDADR 

1993

WGK Germany 

3

RTECS 

LU3580400

F 

1-8-10

HazardClass 

3.2

PackingGroup 

III

HS Code 

29349990

Storage Class

3 - Flammable liquids

Hazard Classifications

Aquatic Chronic 3
Flam. Liq. 3
Skin Sens. 1

MSDS

• Language:English Provider:3-Methylenedihydro-2(3H)-furanone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Tulipalin A Usage And Synthesis

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

Uses

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

Uses

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

Uses

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.

Source

a-Methylene-g-butyrolactone (MBL), also known as Tulipalin A, is found to be present in white tulips. By virtue of its exo-methylene double bond, it can be used as a naturally originated monomer in order to synthesize biopolymers.^[1]

References

[1] SEEMA AGARWAL  Rimpu K. Synthesis of High-Molecular-Weight Tulipalin-A-Based Polymers by Simple Mixing and Heating of Comonomers[J]. Macromolecular Chemistry and Physics, 2011, 212 6: 603-612. DOI:10.1002/macp.201000673.

Tulipalin A(547-65-9)Related Product Information

• Diethylstilbestrol
• Dihydromyrcenol
• Tetrahydrofuran
• 2-Methylfuran
• BETA-BUTYROLACTONE
• Methylene Blue trihydrate
• 2(5H)-Furanone
• Oxymetholone
• 3-Methylfuran
• Furazolidone
• 4,4'-Diphenylmethane diisocyanate
• Methylene Blue
• ZINC ZIRCONATE
• Dimethyl sulfoxide
• Alantolactone
• Parthenolide
• Gamma Butyrolactone
• Methylene Chloride