Tulipalin A

Names

[ CAS No. ]:
547-65-9

[ Name ]:
Tulipalin A

[Synonym ]:
3-Methylenedihydrofuran-2(3H)-one
2(3H)-Furanone, dihydro-3-methylene-
3-methylideneoxolan-2-one
MFCD00005407
EINECS 208-931-6
alpha-methylene gamma-butyrolactone
2-Methylenebutyrolactone
3-Methylenedihydro-2(3H)-furanone
α-Methylene-γ-butyrolactone

Biological Activity

[Description]:

Tulipalin A (α-Methylene butyrolactone) is a toxic glycoside isolated from the tulip bulbs. Tulipalin A is a causative allergen that induces Allergic contact dermatitides[1]. Tulipalin A (α-Methylene butyrolactone) at low dose affects the functionality of immune cells, such as Jurkat T cells[2].

[References]

[1]. Zwicker P, et al.A proteomic approach for the identification of immunotoxic properties of Tulipalin A.Proteomics. 2016 Dec;16(23):2997-3008.

[2]. McCluskey J, et al. Tulipalin A induced phytotoxicity.Int J Crit Illn Inj Sci. 2014 Apr;4(2):181-3.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
204.4±0.0 °C at 760 mmHg

[ Molecular Formula ]:
C₅H₆O₂

[ Molecular Weight ]:
98.100

[ Flash Point ]:
37.2±0.0 °C

[ Exact Mass ]:
98.036781

[ PSA ]:
26.30000

[ LogP ]:
-0.06

[ Vapour Pressure ]:
0.3±0.4 mmHg at 25°C

[ Index of Refraction ]:
1.452

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H226-H317-H412

[ Precautionary Statements ]:
P210-P280-P370 + P378

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R42/43:May cause sensitization by inhalation and skin contact .

[ Safety Phrases ]:
S23-S36/37

[ RIDADR ]:
1993

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
3.2

[ HS Code ]:
2932209090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932209090

[ Summary ]:
2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Design and synthesis of spiro derivatives of parthenin as novel anti-cancer agents.

Eur. J. Med. Chem. 46 , 3210-7, (2011)

Several novel spiro derivatives of parthenin (1) have been synthesized by the dipolar cycloaddition using various dipoles viz; benzonitrile oxides, nitrones and azides with exocyclic double bond of C ...

Construction of spiro-fused 2-oxindole/α-methylene- γ-butyrolactone systems with extremely high enantioselectivity via indium-catalyzed amide allylation of N-methyl isatin.

Org. Lett. 15(24) , 6182-5, (2013)

A remarkably effective method allowing an extremely high enantioselective synthesis of the spiro-fused 2-oxindole/α-methylene-γ-butyrolactones is described. The key strategy lies in the use of indium-...

Highly stereoselective synthesis of (Z)- and (E)-chloro-substituted-α-methylene-γ-butyrolactone by possibly controlling cis- and trans-chloropalladation.

Mol. Divers. 17(1) , 1-7, (2013)

A palladium-catalyzed selective synthesis of cis- or trans-chloro-substituted-α-methylene-γ-butyrolactones from single substrate (propiolic acid) has been realized by controlling cis- or trans-chlorop...