Cinnamic Acid

Cinnamic acid is a metabolite of cinnamaldehyde created in humans by the action of aldehyde dehydrogenase.

The enzyme Phenylalanine ammonia-lyase (PAL, EC, is capable of converting cinnamic acid to L-phenylalanine. Using a culture medium of Rhodotorula glutinis containing PAL, at pH 10.0 cinnamic acid was aminated to L-phenylalanine, but at pH 8.8 L-phenylalanine was deaminated into cinnamic acid.[1]

Substrate PAL Product
Cinnamic acid pH 10 L-phenylalanine
Cinnamic_Acid.png L-Phenylalanine.png

Chemical Properties

Synonyms: trans-cinnamic acid
PubChem Compound ID: 444539
Molecular Weight: 148.15862 [g/mol]
Molecular Formula: C9H8O2
XLogP3: 2.1
H-Bond Donor: 1
H-Bond Acceptor: 2
IUPAC Name: (E)-3-phenylprop-2-enoic acid
InChI: InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)O
Isomeric SMILES: C1=CC=C(C=C1)/C=C/C(=O)O

1. Production of l-Phenylalanine from trans-Cinnamic Acid with Rhodotorula glutinis Containing l-Phenylalanine Ammonia-Lyase Activity
Shigeki Yamada, Koichi Nabe, Nobuhiko Izuo, Katsuhiko Nakamichi, and Ichiro Chibata PubMed PMCID: PMC244106
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