2-acetamidoprop-2-enoic acid

• ChemBase ID: 105907
• Molecular Formular: C5H7NO3
• Molecular Mass: 129.11398
• Monoisotopic Mass: 129.04259309
• SMILES: CC(=O)NC(=C)C(=O)O
• Canonical SMILES: CC(=O)NC(=C)C(=O)O
• InChI: InChI=1S/C5H7NO3/c1-3(5(8)9)6-4(2)7/h1H2,2H3,(H,6,7)(H,8,9)
• InChIKey: UFDFFEMHDKXMBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamidoprop-2-enoic acid
• IUPAC Traditional name: 2-acetamidoprop-2-enoic acid
• Synonyms: N-Acetyldehydroalanine; 2-Acetamidoacrylic acid; 2-ACETAMINOACRYLIC ACID; ACETYLDEHYDROALANINE; 2-ACETAMIDOACRYLIC ACID; 2-(Acetylamino)-2-propenoic Acid; 2-(Acetylamino)acrylic Acid; Acetyldehydroalanine; N-Acetyl-α-aminoacrylic Acid; NSC 14171; Ac-DL-Dha-OH; N-乙酰基脱氢丙氨酸; 2-乙酰氨基丙烯酸; 2-乙酸胺基丙烯酸

Database IDs

• CAS Number: 5429-56-1
• EC Number: 226-583-3
• MDL Number: MFCD00004257
• Beilstein Number: 1812032
• PubChem SID: 24890540; 162087262; 24844986
• PubChem CID: 79482

CALCULATED PROPERTIES

• Acid pKa: 4.057924
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.2580004
• LogD (pH = 7.4): -3.9289546
• Log P: -0.8040447
• Molar Refractivity: 30.3601 cm^3
• Polarizability: 11.539296 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol (Sparingly)
• Apperance: Off-White Solid
• Melting Point: 178-181°C; 185-186 °C (dec.)(lit.); 185-186°C; ca 190°C dec.

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0% (T); 99%
• Grade: puriss.
• Ignition Residue: ≤0.05%
• Impurities: ≤0.6% water
• Linear Formula: CH2=C(NHCOCH3)COOH

DETAILS

MP Biomedicals - 02195054

Purity: >99%

MP Biomedicals - 05220113

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A1401

Packaging
10 g in glass bottle

Toronto Research Chemicals - A137650

An antioxidant.

REFERENCES

• Sappington, P., et al.: Biochem. Pharmacol., 70, 1579 (2005)
• Suzen, S., et al.: J. Enz. Inhibit. Med. Chem., 21, 179 (2005)
• Mazurek, S., et al.: Mol. Divers., 11, 141 (2005)
• Pd-catalyzed arylation by aryl bromides affords pure (Z)-isomers of derivatives of dehydrophenylalanine: Tetrahedron Lett., 24, 4603 (1983).
• For asymmetric hydrogenation using a chiral Rh catalyst, see: Chem. Lett., 305 (1989).
• Reacts with pyrazole in the presence of acetic acid or an acetate buffer to give 2-acetamido-3-(N-pyrazolo)propionic acid which, on hydrolysis, gives the pyrazoloalanine, an unusual naturally occurring amino acid: Chem. Pharm. Bull., 70, 609 (1972):