Table of Contents
Cinnamaldehyde is an aldehyde found in cinnamon bark in high concentrations. It's used as a flavor and medicine. Cinnamon bark is usually used medicinally in doses of 1-6 grams orally. 6 grams of cinnamon can contain from to 42 to 189 mg cinnamaldehyde. Cinnamon contains approximately 1 to 3.5 percent essential oil. The essential oil is approximately 70 to 90 percent cinnamaldehyde.
Metabolism in Humans
In vitro tests using human skin homogenates show that cinnamaldehyde is metabolized by aldehyde dehydrogenase (ALDH). This action is theorized to produce cinnamic acid, a known metabolite of cinnamaldehyde. Another known metabolite of cinnamaldehyde, cinnamic alcohol, was found to be converted back into cinnamaldehyde by the action of alcohol dehydrogenase (ADH).
Cinnamaldehyde reacts spontaneously with glutathione, but it's metabolites cinnamic acid and cinnamyl alcohol do not. In vitro tests using rat hepatocytes found that cinnamaldehyde and cinnamyl alcohol deplete glutathione levels equally, although cinnamyl alcohol has a delayed effect. It's theorized that cinnamyl alcohol only depletes glutathione after conversion into cinnamaldehyde by the action of alcohol dehydrogenase (ADH), which accounts for it's delayed action. Cinnamaldehyde's metabolite cinnamic acid has no effect of glutathione depletion.
Glutathione S-transferase Inhibition
Xanthine Oxidase Inhibition
Aldose Reductase Inhibition
Reactions With Alkaloids and Other Compounds
Like many common aldehydes cinnamaldehyde has been shown to condense with several amines without the need for a catalyst.
Adduct with Dapsone
The adduct AC1MSDH8 is a Schiff base. AC1MSDH8 has been formed by the condensation of 0.264 grams of the aldehyde cinnamaldehyde with 0.281 grams of the alkaloid dapsone in 20 ml ethanol for 5 min while stirring at 60° C forming the Schiff base AC1MSDH8 with a yield of 87%. While heat is used to speed up the reaction, no chemical catalyst is needed.
Adduct with Cysteine
Cinnamaldehyde was found to directly react with the amino acid cysteine, no catalyst is required.
Adduct with Glutathione
Adduct with Phenylacetamide
Adduct with Acetamide
The oral LD50 for cinnamaldehyde is 2.22 to 3.4 g/kg for rats and mice (Opdyke, 1979).
PubChem Compound ID: 637511
Molecular Weight: 132.15922 [g/mol]
Molecular Formula: C9H8O
IUPAC Name: (E)-3-phenylprop-2-enal
Canonical SMILES: C1=CC=C(C=C1)C=CC=O
Isomeric SMILES: C1=CC=C(C=C1)/C=C/C=O
- Aldehyde Adducts
- Lysergic Acid Amide (LSA)
- Lysergic acid hydroxyethylamide (LSH)
- Oilahuasca Activation