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About This Item
Linear Formula:
H2C=C(NHCOCH3)CO2CH3
CAS Number:
Molecular Weight:
143.14
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23
Recommended Products
Assay
98%
bp
104 °C/8 mmHg (lit.)
mp
50-52 °C (lit.)
SMILES string
COC(=O)C(=C)NC(C)=O
InChI
1S/C6H9NO3/c1-4(6(9)10-3)7-5(2)8/h1H2,2-3H3,(H,7,8)
InChI key
SMWNFFKPVLVOQQ-UHFFFAOYSA-N
Related Categories
General description
Conjugated addition of secondary amines, imidazole and pyrazole to methyl 2 methyl 2-acetamidoacrylate in the presence of a catalyst results in the formation of β-Dialkylamino-α-alanine and β-(N-heteroaryl)-α-alanine derivatives. Methyl-2-acetamidoacrylate (M2AA) is an anti-inflammatory agent. The catalytic reaction of methyl 2-acetamidoacrylate with Grignard′s reagents affords α-amino esters. M2AA can form thermosensitive copolymers with methyl acrylate.
Methyl ester of 2-acetamidoacrylate . methyl 2-acetamidoacrylate (Me-2-AA) is a di-unsaturated α-amino acid derivative. methyl-2-acetamidoacrylate exihibits anti -inflammatory properties, it is very effective against lipopolysaccharide (LPS)- induced nitric oxide production by RAW 264.
Application
Methyl 2-acetamidoacrylate can undergo [2+2] cycloaddition (Michael–Dieckmann-type reaction) with ketene diethyl acetal to yield the cyclobutane core. It may be used in rhodium-catalyzed 2-alkenylpyrrole formation.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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William P Hems et al.
Organic & biomolecular chemistry, 3(8), 1547-1550 (2005-04-14)
Rh diphosphine complexes using DuPhos and JosiPhos as chiral ligands have been immobilised by ion exchange into the mesoporous material MCM-41. When used as catalysts for the enantioselective hydrogenation of dimethyl itaconate and methyl-2-acetamidoacrylate, these heterogeneous catalysts give catalytic performance
Asada Leelahavanichkul et al.
American journal of physiology. Renal physiology, 295(6), F1825-F1835 (2008-10-17)
We tested the anti-inflammatory agent methyl-2-acetamidoacrylate (M2AA), an ethyl pyruvate analog, in a cecal ligation-and-puncture (CLP) model of sepsis in CD-1 mice. M2AA administration at the time of CLP improved survival, renal function, kidney histology, liver injury, and splenocyte apoptosis
Synthesis of 2-methyl- and 2-methylenecyclobutane amino acids
Avenoza A, et al.
Tetrahedron, 61(16), 4165-4172 (2005)
Penny L Sappington et al.
Biochemical pharmacology, 70(11), 1579-1592 (2005-10-18)
Ethyl pyruvate (EP) is a simple aliphatic ester derived from the endogenous metabolite, pyruvic acid. EP has been shown to decrease the expression of various pro-inflammatory mediators, including nitric oxide (NO*), tumor necrosis factor (TNF), cyclooxygenase-2, and interleukin (IL)-6, in
Orthogonal synthesis of indolines and isoquinolines via aryne annulation.
Christopher D Gilmore et al.
Journal of the American Chemical Society, 130(5), 1558-1559 (2008-01-16)
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