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Sigma-Aldrich

α-Acetamidocinnamic acid

98%

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Synonym(s):
N-Acetyldehydrophenylalanine
Linear Formula:
C6H5CH=C(NHCOCH3)COOH
CAS Number:
5469-45-4
Molecular Weight:
205.21
Beilstein:
1912549
EC Number:
226-795-6
MDL number:
MFCD00008680
UNSPSC Code:
12352100
PubChem Substance ID:
24852809
NACRES:
NA.22

Assay

98%

mp

188-190 °C (lit.)

solubility

methanol: soluble 100 mg/mL, clear, yellow-green
95% ethanol: soluble 5%, clear, yellow

SMILES string

CC(=O)N\C(=C/c1ccccc1)C(O)=O

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)/b10-7-

InChI key

XODAOBAZOQSFDS-YFHOEESVSA-N

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General description

Asymmeteric hydrogenation of α-acetamidocinnamic acid with chiral rhodium (I) complexes on charcoal has been reported. α-Acetamidocinnamic acid undergoes asymmetric hydrogenation in ionic liquid catalyzed by rhodium complex to yield (S)-phenylalanine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Choong Eui Song
Chemical communications (Cambridge, England), 9(9), 1033-1043 (2004-04-30)
Recent developments in the enantioselective chemo- and bio-catalysis in ionic liquids are reviewed. In many cases, the use of ionic liquids provides many advantages over reactions in conventional organic solvents in terms of activity, enantioselectivity, stability and the reusability of
Asymmetric hydrogenation of a-acetamidocinnamic acid with chiral rhodium complexes of DIOP and BPPM on charcoal.
Masami I, et al.
Chemical & Pharmaceutical Bulletin, 31(10), 3371-3376 (1983)

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