Tulipalin A

Tulipalin A Basic information

Product Name:	Tulipalin A
Synonyms:	ALPHA-METHYLENE-GAMMA-BUTYROLACTONE, STA B.;Stabilizedwith2,6-Ditert-butyl-p-cresol;alpha-Methylene-gamma-butyrolactone (stabilized with 2,6-Di-tert-butyl-p-cresol);3-Methylenedihydro-2(3H)-furanone, Tulipane;2-Methylene-g-butyrolactone;4,5-Dihydro-3-methylene-2(3H)-furanone;a-Methylenebutyrolactone;Tetrahydro-3-methylene-2-furanone
CAS:	547-65-9
MF:	C5H6O2
MW:	98.1
EINECS:	208-931-6
Product Categories:	Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactones;Organic Building Blocks
Mol File:	547-65-9.mol

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.)
Fp	99 °F
storage temp.	2-8°C
solubility	water: soluble(lit.)
form	Liquid
color	Clear colorless to light yellow or slightly pink
Merck	14,6062
BRN	107939
InChIKey	GSLDEZOOOSBFGP-UHFFFAOYSA-N
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

MSDS Information

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

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	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.
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.
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.

Tulipalin A Preparation Products And Raw materials

Raw materials

2(5H)-Furanone, 3-(bromomethyl)--->carbon monoxide-->Butanoic acid, 4-hydroxy-2-methylene-, methyl ester-->3-BUTENYL CHLOROFORMATE-->(2-Oxotetrahydrofuran-3-yl)phosphonic acid diethyl ester-->2-Oxo-tetrahydro-furan-3-carbaldehyde-->3-METHYL-2(5H)-FURANONE-->VINYL ACRYLATE-->Dimethylamine-->2-Chloro-4,6-dimethoxy-1,3,5-triazine-->3-Butyn-1-ol-->Formaldehyde-->4-ethoxy-2-methylenbutyraldehyde-->Ethyl formate-->Acrylic acid

BETA-BUTYROLACTONE Alantolactone Tulipalin A Parthenolide CNICIN 5-METHYLENEDIHYDRO-2(5H)-FURANONE,αμ-Angelicalactone, 5-Methylenedihydro-2(3H)-furanone ISOOCTADECENYLSUCCINIC ANHYDRIDE 3-BENZYLIDENE-DIHYDRO-FURAN-2-ONE POLY(TETRAHYDROFURAN) STANDARD 20000 AKOS NCG1-0061 5,5-DIMETHYL-3-METHYLENEDIHYDRO-2[3H]-FURANONE ZINC ZIRCONATE 4,4'-Diphenylmethane diisocyanate Furazolidone Dihydromyrcenol Isoalantolactone Gamma Butyrolactone Diethylstilbestrol

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