Tulipalin A

Tulipalin A
Names
	IUPAC name α-methylene-γ-butyrolactone
	Preferred IUPAC name 3-Methylideneoxolan-2-one
	Other names TUPA;
Identifiers
CAS Number	547-65-9;
3D model (JSmol)	Interactive image;
Beilstein Reference	107939
ChEBI	CHEBI:104120;
ChemSpider	61647;
ECHA InfoCard	100.008.120
EC Number	208-931-6;
Gmelin Reference	746139
PubChem CID	68352;
UNII	362Y256BOL;
CompTox Dashboard (EPA)	DTXSID2074663 ;
	InChI InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2 Key: GSLDEZOOOSBFGP-UHFFFAOYSA-N;
	SMILES C=C1CCOC1=O;
Properties
Chemical formula	C5H6O2
Molar mass	98.101 g·mol−1
Density	1.085 g/ml
Melting point	25 °C (77 °F; 298 K)
Boiling point	168 °C (334 °F; 441 K)
Solubility in water	Soluble in organic solvents like acetone and slightly soluble in water
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H317
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P272, P280, P302+P352, P303+P361+P353, P321, P333+P313, P363, P370+P378, P403+P235, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tulipalin A, also known as α-methylene-γ-butyrolactone,^[1] is a naturally occurring compound found in certain flowers such as tulips and alstroemerias.^[2] Tulipalin A has the molecular formula C₅H₆O₂ and the CAS registry number 547-65-9.^[1] It is an allergen and has been known to cause occupational contact dermatitis, i.e. 'tulip fingers,' in some who are commonly exposed to it such as florists.^[3] It has been shown to be synthesized from tuliposide A in response to damage to the plant. When the plant is damaged, tuliposide A is broken down by tuliposide-converting enzymes (TCE) to produce tulipalin A. More recent experiments with this compound have uncovered potential applications for it in the field of polymerization.^[4]^[5]

References

^ ^a ^b CID 68352 from PubChem
^ Christensen, Lars P. (1999). "Direct release of the allergen tulipalin a from Alstroemeriacut flowers: A possible source of airborne contact dermatitis?". Contact Dermatitis. 41 (6): 320–324. doi:10.1111/j.1600-0536.1999.tb06180.x. PMID 10617212. S2CID 23478644.
^ McCluskey, J.; Bourgeois, M.; Harbison, R. (2014). "Tulipalin a induced phytotoxicity". International Journal of Critical Illness and Injury Science. 4 (2): 181–183. doi:10.4103/2229-5151.134187. PMC 4093970. PMID 25024947.
^ Zhou, Jiawen; Schmidt, Annette M.; Ritter, Helmut (2010). "Bicomponent Transparent Polyester Networks with Shape Memory Effect". Macromolecules. 43 (2): 939–942. Bibcode:2010MaMol..43..939Z. doi:10.1021/ma901402a.
^ Shin, Jihoon; Lee, Youngmin; Tolman, William B.; Hillmyer, Marc A. (2012). "Thermoplastic Elastomers Derived from Menthide and Tulipalin A". Biomacromolecules. 13 (11): 3833–3840. doi:10.1021/bm3012852. PMID 23062206.

[PubChem-1] CID 68352 from PubChem

[2] Christensen, Lars P. (1999). "Direct release of the allergen tulipalin a from Alstroemeriacut flowers: A possible source of airborne contact dermatitis?". Contact Dermatitis. 41 (6): 320–324. doi:10.1111/j.1600-0536.1999.tb06180.x. PMID 10617212. S2CID 23478644.

[3] McCluskey, J.; Bourgeois, M.; Harbison, R. (2014). "Tulipalin a induced phytotoxicity". International Journal of Critical Illness and Injury Science. 4 (2): 181–183. doi:10.4103/2229-5151.134187. PMC 4093970. PMID 25024947.

[4] Zhou, Jiawen; Schmidt, Annette M.; Ritter, Helmut (2010). "Bicomponent Transparent Polyester Networks with Shape Memory Effect". Macromolecules. 43 (2): 939–942. Bibcode:2010MaMol..43..939Z. doi:10.1021/ma901402a.

[5] Shin, Jihoon; Lee, Youngmin; Tolman, William B.; Hillmyer, Marc A. (2012). "Thermoplastic Elastomers Derived from Menthide and Tulipalin A". Biomacromolecules. 13 (11): 3833–3840. doi:10.1021/bm3012852. PMID 23062206.

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