tulipalin A
{{Chembox
| ImageFile = Tulipalin_A.svg
| ImageSize = 120px
| PIN = 3-Methylideneoxolan-2-one
| OtherNames = {{Unbulleted list|TUPA}}
| IUPACName = α-methylene-γ-butyrolactone
| Section1 = {{Chembox Identifiers
| PubChem = 68352
| ChemSpiderID = 61647
| CASNo = 547-65-9
| EC_number = 208-931-6
| UNII = 362Y256BOL
| ChEBI = 104120
| Beilstein = 107939
| Gmelin = 746139
| StdInChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
| StdInChIKey = GSLDEZOOOSBFGP-UHFFFAOYSA-N
| SMILES = C=C1CCOC1=O
}}
| Section2 = {{Chembox Properties
| C=5|H=6|O=2
| BoilingPtC = 168
| Density = 1.085 g/ml
| MeltingPtC = 25
| Solubility = Soluble in organic solvents like acetone and slightly soluble in water }}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|226|317}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|272|280|302+352|303+361+353|321|333+313|363|370+378|403+235|501}}
}}
}}
Tulipalin A, also known as α-methylene-γ-butyrolactone,{{PubChem|68352}} is a naturally occurring compound found in certain flowers such as tulips and alstroemerias.{{cite journal | doi = 10.1111/j.1600-0536.1999.tb06180.x| title = Direct release of the allergen tulipalin a from Alstroemeriacut flowers: A possible source of airborne contact dermatitis?| journal = Contact Dermatitis| volume = 41| issue = 6| pages = 320–324| year = 1999| last1 = Christensen| first1 = Lars P.| pmid = 10617212| s2cid = 23478644}} Tulipalin A has the molecular formula C5H6O2 and the CAS registry number 547-65-9. 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.{{cite journal | pmc = 4093970| year = 2014| last1 = McCluskey| first1 = J.| title = Tulipalin a induced phytotoxicity| journal = International Journal of Critical Illness and Injury Science| volume = 4| issue = 2| pages = 181–183| last2 = Bourgeois| first2 = M.| last3 = Harbison| first3 = R.| pmid = 25024947| doi = 10.4103/2229-5151.134187| doi-access = free}} 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.{{cite journal | doi = 10.1021/ma901402a| title = Bicomponent Transparent Polyester Networks with Shape Memory Effect| journal = Macromolecules| volume = 43| issue = 2| pages = 939–942| year = 2010| last1 = Zhou| first1 = Jiawen| last2 = Schmidt| first2 = Annette M.| last3 = Ritter| first3 = Helmut| bibcode = 2010MaMol..43..939Z}}{{cite journal | doi = 10.1021/bm3012852| pmid = 23062206| title = Thermoplastic Elastomers Derived from Menthide and Tulipalin A| journal = Biomacromolecules| volume = 13| issue = 11| pages = 3833–3840| year = 2012| last1 = Shin| first1 = Jihoon| last2 = Lee| first2 = Youngmin| last3 = Tolman| first3 = William B.| last4 = Hillmyer| first4 = Marc A.}}