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Cinnamic acid

3-Phenyl-2-propenoic acid

β-Phenylacrylic acid · trans-Cinnamic acid

Phenylpropenoid carboxylic acid · C₉H₈O₂

Chemical structure of Cinnamic acid
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
140-10-3
Molecular formula
C₉H₈O₂
Molecular weight
148.16 g/mol
Aroma
Warm balsamic, honeyed sweet, with a soft cinnamon finish.

Safety

Low concern · Cross-reacts with Peru balsam

Cinnamic acid is a natural metabolite of cinnamaldehyde and a common balsam constituent.

Skin. A 4 percent patch test on 25 volunteers caused no irritation or sensitization. Among Peru balsam sensitized patients, 32 of 128 (25 percent) reacted to 5 percent. In 184 Japanese patients, none reacted at 2 percent and one at 5 percent.

Oral. Acute oral LD50 is 2.5–5 g/kg across rats, mice and guinea pigs; rabbit dermal LD50 exceeds 5 g/kg.

Reproductive. Oral 5 or 50 mg/kg throughout pregnancy in rats produced no embryotoxic effects. Pup weight, size, survival and development were normal. The compound did not bind to estrogen receptors in rat uterine tissue.

Liver. Does not deplete hepatic glutathione.

Mutagenicity. Non-mutagenic in the Ames test. Non-mutagenic in the SOS chromotest and Bacillus subtilis rec assay. Weak genotoxic activity in Chinese hamster ovary cells.


Usage guidelines

Concern level
Low · cross-reactive with Peru balsam
Oils with high content
Peru balsam 0–5.8 percent · Styrax 4.0–4.8 percent · Boronia 4.3 percent

Found in essential oils

Principal sources
Peru balsam0 – 5.8 %
Styrax4.0 – 4.8 %
Boronia1.9 – 4.3 %
Tolu balsam2.7 %
Benzointr – 1.4 %
Labdanum0 – 1.4 %

Pharmacokinetics

Cinnamic acid is generated in vivo from oxidation of cinnamaldehyde. Most is excreted as hippuric acid: 39–74 percent in dogs, cats, rats and rabbits. In humans 50–87 percent as hippuric acid and 1–6 percent as cinnamoyl glucuronide.

In mice, depending on intraperitoneal dose, 44–70 percent is excreted as hippuric acid (rising with dose) and 2.4–28.6 percent as cinnamoylglycine.


Notes

Cinnamic acid is a foundational constituent for balsamic notes and a natural auxiliary for cinnamon aromas. The compound also weakly inhibits monoamine oxidase.