Tulipalin A

From Wikipedia, the free encyclopedia
Tulipalin A
Tulipalin A.svg
Names
Preferred IUPAC name
3-Methylideneoxolan-2-one
Other names
α-Methylene-γ-butyrolactone
Identifiers
3D model (JSmol)
107939
ChEBI
ChemSpider
ECHA InfoCard 100.008.120 Edit this at Wikidata
EC Number
  • 208-931-6
746139
UNII
  • InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
    Key: GSLDEZOOOSBFGP-UHFFFAOYSA-N
  • C=C1CCOC1=O
Properties
C5H6O2
Molar mass 98.101 g·mol−1
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H317
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).

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] More recent experiments with this compound have uncovered potential applications for it in the field of polymerization.[4][5]

References[edit]

  1. ^ a b 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.
  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.