2-acetamido-3-phenylprop-2-enoic acid

• ChemBase ID: 89434
• Molecular Formular: C11H11NO3
• Molecular Mass: 205.20994
• Monoisotopic Mass: 205.07389322
• SMILES: N(/C(=C\c1ccccc1)/C(=O)O)C(=O)C
• Canonical SMILES: OC(=O)/C(=C/c1ccccc1)/NC(=O)C
• InChI: InChI=1S/C11H11NO3/c1-8(13)12-10(11(14)15)7-9-5-3-2-4-6-9/h2-7H,1H3,(H,12,13)(H,14,15)
• InChIKey: XODAOBAZOQSFDS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-phenylprop-2-enoic acid; (2Z)-2-acetamido-3-phenylprop-2-enoic acid
• IUPAC Traditional name: 2-acetamido-3-phenylprop-2-enoic acid; (2Z)-2-acetamido-3-phenylprop-2-enoic acid
• Synonyms: trans-2-Acetamido-3-phenylacrylic acid; alpha-Acetamidocinnamic acid; N-Acetyldehydrophenylalanine; α-Acetamidocinnamic acid; α-ACETAMINOCINNAMIC ACID; 4-Hydroxy-3,5-diiodobenzeneacetic Acid; (4-Hydroxy-3,5-diiodophenyl)acetic Acid; α-(3,5-Diiodo-4-hydroxyphenyl)acetic Acid; 3,5-Diiodo-4-hydroxyphenylacetic Acid; Acetamidocinnamic acid; α-ACETOAMINOCINNAMIC ACID; 2-(Acetylamino)-3-phenyl-2-propenoic Acid; α-Acetylaminocinnamic Acid; 2-Acetylamino-3-phenylacrylic Acid; NSC 25333; α-Acetamidocinnamic Acid; N-乙酰基脱氢苯丙氨酸; α-乙酰氨基肉桂酸

Database IDs

• CAS Number: 5469-45-4; 1948-39-6
• EC Number: 226-795-6
• MDL Number: MFCD00188416; MFCD00008680
• Beilstein Number: 1912549
• PubChem SID: 24852809; 162076314; 24845018; 24845017
• PubChem CID: 5370579

CALCULATED PROPERTIES

• Acid pKa: 3.946029
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.7622683
• LogD (pH = 7.4): -2.3901093
• Log P: 0.79909426
• Molar Refractivity: 56.1286 cm^3
• Polarizability: 21.098364 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 188-190 °C(lit.); 188-190°C; 188-190°C; 190-193 °C; 192-194 °C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (T); 98%
• Grade: puriss.; purum
• Linear Formula: C6H5CH=C(NHCOCH3)COOH

DETAILS

MP Biomedicals - 05219101

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 213853

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 00385

Application
test substance for asymmetric hydrogenations

Toronto Research Chemicals - A150000

A protein kinase C inhibitor.

Toronto Research Chemicals - D455180

3,5-Diiodo-4-hydroxyphenylacetic acid is an impurity of Thyroxine (T425600).

REFERENCES

• Pitt-Rivers, R., et al.: Biochem. J., 70, 173 (1958)
• Cereijo-Santalo, R., et al.: Endocrinology, 69, 422 (1958)
• Singh, T., et al.: Adv. Exp. Med. Biol., 379, 11 (1996)
• Varnavas, A., et al.: Eur. J. Med. Chem., 39, 85 (1996)