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Cinnamyl alcohol

Cinnamic alcohol Styryl carbinol Phenylallyl alcohol Styron

Cinnamyl alcohol or styron is an organic compound that is found in esterified form in storax, Balsam of Peru, and cinnamon leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the hydrolysis of storax.

Cinnamyl alcohol occurs naturally only in small quantities, so its industrial demand is usually fulfilled by chemical synthesis starting from cinnamaldehyde.

Properties

The compound is a solid at room temperature, forming colorless crystals that melt upon gentle heating. As is typical of most higher-molecular weight alcohols, it is sparingly soluble in water at room temperature, but highly soluble in most common organic solvents.

Uses

Cinnamyl alcohol has a distinctive odor described as "sweet, balsam, hyacinth, spicy, green, powdery, cinnamic" and is used in perfumery and as a deodorant.

Cinnamyl alcohol is the starting material used in the synthesis of reboxetine.

There is basic medical research investigating the neuroprotective properties of cinnamyl alcohol in terms of the following with respect to epilepsy:

  • Potentiating the GABAergic system
  • Promoting antioxidant effects
  • Reducing pro-inflammatory mediators activities.

Safety

Cinnamyl alcohol has been found to have a sensitizing effect on some people and as a result is the subject of a Restricted Standard issued by IFRA (International Fragrance Association).

Glycosides

Rosarin and rosavin are cinnamyl alcohol glycosides isolated from Rhodiola rosea.

References

References

  1. ''Merck Index'', 11th Edition, '''2305'''
  2. [https://books.google.com/books?id=15wEAAAAYAAJ ''Chemical News and Journal of Industrial Science'', Volumes 27-28, Sir William Crookes, page 126]
  3. (May 2009). "Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol.". Bioscience, Biotechnology, and Biochemistry.
  4. "cinnamyl alcohol 104-54-1". thegoodscentscompany.com.
  5. "Reboxetine mesilate".
  6. (2024). "Neuroprotective effect of cinnamic alcohol: A bioactive compound of ''Cinnamomum'' spp. essential oil". Neurochemistry International.
  7. (2007). "Food and Chemical Toxicology". RIFM.
  8. [http://www2.mst.dk/udgiv/publications/2006/87-7052-278-2/html/kap07_eng.htm Survey and health assessment of chemical substances in massage oils] {{webarchive. link. (2007-06-28)
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flavors primary-alcohols phenylpropanoids perfume-ingredients
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