Cinnamaldehyde

OVERVIEW

Cinnamaldehyde (sin-uh-MAL-duh-hide) is also known as cinnamic aldehyde; 3-phenyl-2-propenal; cinnamyl aldehyde; phenylalacrolein; cinnamal; and trans-cinnamaldehyde. It is a yellowish oily, liquid with a sweet taste and a cinnamish odor responsible for the characteristic taste and odor of cinnamon spice. It occurs naturally in the bark of the cinnamon tree, Cinnamomum zeylanicum, which is native to Sri Lanka and India, and has been cultivated in other parts of the world, such as Brazil, Jamaica, and Mauritius. Cinnamaldehyde is also found in other members of the the Cinnamomum> species, including cassia and camphor.

The molecular formula for cinnamaldehyde was determined in 1834 by the French chemists Jean Baptiste André Dumas (1800–1884) and Eugène Melchior Péligot (1811–1890), although its structural formula was deciphered only in 1866 by the German chemist Emil Erlenmeyer (1825–1909).

KEY FACTS

OTHER NAMES:

See Overview.

FORMULA:

C₆H₅CH=CHCHO

ELEMENTS:

Carbon, hydrogen, oxygen

COMPOUND TYPE:

Aromatic aldehyde (organic)

STATE:

Liquid

MOLECULAR WEIGHT:

132.16 g/mol

MELTING POINT:

−7.5°C (18°F)

BOILING POINT:

246°C (475°F)

SOLUBILITY:

Very slightly soluble in water; soluble in alcohol, ether, and chloroform

Primary uses for Cinnamaldehyde are as a food flavoring and a medical herb. It has been used for many centuries to treat a wide variety of disorders, ranging from the common cold and the flu to diarrhea to cancer. It was mentioned in Chinese medical texts as early as 2700 bce and was described in a famous Chinese medical text, the Tang Materia Medica, written in 659 ce It has also been used for centuries in Ayurvedic medicine, the ancient healing art of India.

HOW IT IS MADE

Cinnamaldehyde is prepared commercially by treating the bark of the Cinnamomum zeylanicum tree with steam. The aldehyde dissolves in the steam and can then be extracted as the steam cools and condenses to form cold water, in which the compound is much less soluble. Cinnamaldehyde can also be synthesized by reacting benzaldehyde (C₆H₅CHO) with acetaldehyde (CH₃CHO). The two compounds condense with the elimination of water to form cinnamaldhyde.

COMMON USES AND POTENTIAL HAZARDS

In addition to its uses as a herbal remedy, the primary use of cinnamaldehyde is as a food additive to enhance the flavor and/or odor of food products. It is used most commonly in cake mixes, chewing gums, chocolate products, synthetic cinnamon oils, cola drinks, ice creams, soft drinks, and vermouth. The compound is also added to a number of cosmetics and home care products to improve their odor. Such products include deodorants, detergents, mouthwashes, perfumes, sanitary napkins, soaps, and toothpastes. Finally, cinnamaldehyde is used to some extent in agriculture as an insecticide and fungicide.

Interesting Facts

• Cinnamaldehyde is a component of sprays used as cat and dog repellents.

Words to Know

AROMATIC COMPOUND

A compound whose chemical structure is based on that of benzene (C₆H₆).

SYNTHESIS

A chemical reaction in which some desired chemical product is made from simple beginning chemicals, or reactants.

No safety concerns about the use of cinnamaldehyde as an herbal remedy, food additive, or pesticide has been expressed. The U.S. Food and Drug Administration (FDA) has classified the compound as a generally-recognized as safe (GRAS) food additive, permitting its continued use as a food additive in the United States.

FOR FURTHER INFORMATION

"Cinnamaldehyde." Chemical Land 21. http://www.chemicalland21.com/arokorhi/specialtychem/perchem/CINNAMALDEHYDE.htm (accessed on October 3, 2005).

"Cinnamaldehyde (040506) Fact Sheet." U.S. Environmental Protection Agency. http://www.epa.gov/pesticides/biopesticides/ingredients/factsheets/factsheet_040506.htm (accessed on October 3, 2005).

"Oleum Cinnamomi (U. S. P.)—Oil of Cinnamon." King's American Dispensatory (1898). http://www.ibiblio.org/herbmed/eclectic/kings/cinnamomum_oleu.html (accessed on October 3, 2005).