trans-Cinnamaldehyde

Absorption

Cinnamaldehyde is 52% absorbed through the skin and shown to be rapidly absorbed from the gut .

Description

trans-Cinnamaldehyde, as its name suggests, is a natural product that occurs in cinnamon oils. Its cis counterpart is not found in nature; thus, “trans” is often omitted from its name.
As early as the 1830s, chemists reported synthesizing cinnamaldehyde via the aldol condensation of benzaldehyde and acetaldehyde. But the most economical way of producing it is still by steam distilling the bark of trees in the genus Cinnamomum.
Cinnamaldehyde is an important flavoring in foods (e.g., candy and cookies) and an odorant for perfumes. It has also been used to eradicate mosquito larvae and repel adult mosquitoes. Because it exists naturally, it is suitable for organic agriculture.
Now for a different take on cinnamaldehyde. Halloween is almost here, with its ghosts, witches, hobgoblins—and mummies. It turns out that the ancient Egyptians (ca. 2600 BCE) used the bark of cassia trees (Cinnamomum cassia) as an insecticide to help preserve mummies and give them a pleasing aroma.
Happy Halloween to you and your mummy!

Chemical properties

CLEAR YELLOW LIQUID

Chemical properties

Combustible, yellowish, oily liquid (thickens on exposure to air). Strong pungent, spicy, cinnamon odor.

Chemical properties

trans-Cinnamaldehyde is the main component of cassia oil (about 90%) and Sri Lanka cinnamon bark oil (about 75%). Smaller quantities are found in many other essential oils. In nature, the trans-isomer is predominant.
trans-Cinnamaldehyde is a yellowish liquid with a characteristic spicy odor, strongly reminiscent of cinnamon. Being an ??,??-unsaturated aldehyde, it undergoes many reactions, of which hydrogenation to cinnamic alcohol, dihydrocinnamaldehyde, and dihydrocinnamic alcohol is important. Cinnamic acid is formed by autoxidation.
On an industrial scale, cinnamaldehyde is prepared almost exclusively by alkaline condensation of benzaldehyde and acetaldehyde. Self-condensation of acetaldehyde can be avoided by using an excess of benzaldehyde and by slowly adding acetaldehyde.
Cinnamaldehyde is used in many compositions for creating spicy and oriental notes (e.g., soap perfumes). It is the main component of artificial cinnamon oil. In addition, it is an important intermediate in the synthesis of cinnamic alcohol and dihydrocinnamic alcohol.

The Uses of trans-Cinnamaldehyde

trans-Cinnamaldehyde is used in the flavor and perfume industry. It is also used in medicine. It reacts with glutathione to get an adduct 1'-(glutathion-S-yl)-dihydrocinnamaldehyde. It is used to prepare cinnamylidene-bisacetamide by reacting with acetamide. Further, it inhibits xanthine oxidase.

The Uses of trans-Cinnamaldehyde

Buildingblock - Cinnamaldehyde is an unsaturated aldehyde so it can easily react to many different compounds to be used in a wide range of fragrance compositions. It is also a building block for several agrochemicals (miticides) or for derivatives like cinnamic alcohol, 3-phenylpropanol, cinnamonitrile, 3-phenylpropionylaldehyde (fragrances and as an alternative to enalapril, lisinopril and ramipril).

Indications

Cinnamaldehyde is approved by the FDA for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

Background

Cinnamaldehyde is a naturally occurring flavonoid that gives the spice cinnamon its flavour and odour. It occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum such as camphor and cassia.
Sensitivity to cinnamaldehyde may be identified with a clinical patch test.

Definition

ChEBI: The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.

Synthesis Reference(s)

Chemistry Letters, 12, p. 1207, 1983
Journal of the American Chemical Society, 93, p. 2080, 1971 DOI: 10.1021/ja00737a057
Tetrahedron Letters, 18, p. 1215, 1977

General Description

Clear yellow liquid with an odor of cinnamon and a sweet taste.

Air & Water Reactions

May be sensitive to prolonged exposure to air and light. Insoluble in water.

Reactivity Profile

trans-Cinnamaldehyde is incompatible with strong oxidizing agents and strong bases. trans-Cinnamaldehyde can also react with sodium hydroxide.

Fire Hazard

trans-Cinnamaldehyde is combustible.

Potential Exposure

Botanical fungicide and insecticide. Used as an antifungal agent, corn rootworm attractant, and dog and cat repellent. Can be used on soil casing for mushrooms, row crops, turf, and all food commodities. Not listed for use in EU countries.

Metabolism

Not Available

Shipping

UN1989 Aldehydes, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid

Incompatibilities

Aldehydes are frequently involved in selfcondensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, ketones, azo dyes, caustics, boranes, hydrazines

Waste Disposal

Incineration. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.