213853
α-Acetamidocinnamic acid
98%
Synonym(s):
N-Acetyldehydrophenylalanine
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About This Item
Linear Formula:
C6H5CH=C(NHCOCH3)COOH
CAS Number:
Molecular Weight:
205.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
226-795-6
Beilstein/REAXYS Number:
1912549
MDL number:
Assay:
98%
InChI key
XODAOBAZOQSFDS-YFHOEESVSA-N
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-
SMILES string
CC(=O)N\C(=C/c1ccccc1)C(O)=O
assay
98%
mp
188-190 °C (lit.)
solubility
methanol: soluble 100 mg/mL, clear, yellow-green, 95% ethanol: soluble 5%, clear, yellow
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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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