alpha-Methylene butyrolactone
Basic information
- CAS
547-65-9- Standard SMILES
C=C1CCOC1=O- InChIKey
GSLDEZOOOSBFGP-UHFFFAOYSA-N- Molecular formula
- C5H6O2
- Average molar mass
- 98.1 g/mol
- Monoisotopic mass
- 98.03677943
Overview
Alpha-methylene gamma-butyrolactone is a butan-4-olide having a methylene group at the 3-position. It has a role as an anti-ulcer drug and a gastrointestinal drug.
Names & identifiers
- Preferred name
- alpha-Methylene butyrolactone
- IUPAC
- 3-methylideneoxolan-2-one
- English name
- Tulipalin A
- Molecular formula
- C5H6O2
- Molecular weight
- 98.1
Names & synonyms
547-65-9alpha-Methylene-gamma-butyrolactoneTulipalin A3-methylideneoxolan-2-one3-Methylenedihydro-2(3H)-furanone3-methylenedihydrofuran-2(3H)-onealpha-Methylene butyrolactone2(3H)-Furanone, dihydro-3-methylene-Dihydro-3-methylene-2(3H)-furanoneSecurolidealpha-methylene gamma-butyrolactone.alpha.-Methylene butyrolactone
Show more names
α-methylene-γ-butyrolactoneTULIPANETulipalin2-METHYLENEBUTYROLACTONEα-Methylene-γ-butyrolactoneMBPD3-Methylenetetrahydrofuran-2-one
EINECS 208-931-6NSC 205367.alpha.-Methylene-.gamma.-butyrolactoneAI3-63021CHEBI:1041202-Methylenebutanolactone362Y256BOLTULIPALIN 98
Database identifiers
- CAS
547-65-9- PubChem CID
- 68352
- DTXSID
DTXSID2074663- ChEMBL
CHEMBL275748- ChEBI
CHEBI:104120- UNII
- 362Y256BOL
- EC Number
- 208-931-6
- Nikkaji
- J100.706H
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 115
Physicochemical properties
- Melting point
- 25 °C · 25 °C (77 °F; 298 K)
- Boiling point
- 168 °C · 168 °C (334 °F; 441 K)
- Density
- 1.085 g/ml · 1.085 g/ml
- refractive index
- 1.47 · 1.47
- Flash point
- 90 °C · 90 °C
- storage temp.
- 2 · 2-8°C
- solubility
- water: soluble(lit.)
- form
- clear liquid
- color
- Colorless to Yellow
- Water Solubility
- water: soluble(lit.)
- Merck
- 14 · 14,6062
- BRN
- 107939 · 107939
- Cosmetics Ingredients Functions
- SKIN PROTECTING
- InChI
- 1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
- InChIKey
- GSLDEZOOOSBFGP-UHFFFAOYSA-N
- SMILES
- C=C1CCOC1=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P272, P280, P302+P352, P303+P361+P353, P321, P333+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesFlam. Liq. 3 (100%)
Safety data
- F
- 1-8-10
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- LU3580400
- ridadr
- 1993
- hs_code
- 2934999090
- risk_code
- 42/43-52/53-10
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xn
- safety_code
- 23-36/37-61-45
- hazard_class
- 3.2
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226-H317-H412
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Applications
DescriptionTulipalin 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.
UsesVery reactive Michael-acceptor; the α-methylene-γ-butyrolactone ring system exists in many natural products of biological interest
UsesAllergen in the Liliaeeae family of plants to whieh speeies such as Tulip, Alstromeria, Erythronium dens canis and americanum belong.
Usesα-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.
Upstream & downstream products
Upstream raw materials
Related reactions
29 records
Compound notes
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