Cinnamyl alcohol

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Cinnamyl alcohol
Skeletal formula
A sample of cinnamyl alcohol on a petri dish.
Names
IUPAC name
(2E)-3-phenylprop-2-en-1-ol
Other names
Cinnamyl alcohol
Cinnamic alcohol
Styryl carbinol
Phenylallyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.921
KEGG
Properties
C9H10O
Molar mass 134.17 g/mol
Density 1.0397 g/cm3 at 35 °C
Melting point 33 °C
Boiling point 250 °C
Slightly
Solubility soluble in ethanol, acetone, dichloromethane
-87.2·10−6 cm3/mol
Hazards
Safety data sheet External MSDS
Related compounds
Related compounds
Cinnamic acid; Cinnamaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cinnamyl alcohol 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 has a distinctive odour described as "sweet, balsam, hyacinth, spicy, green, powdery, cinnamic" and is used in perfumery[1] and as a deodorant.

Cinnamyl alcohol is naturally occurrent only in small amount, so its industrial demand is usually fulfilled by chemical synthesis starting from cinnamaldehyde.[2]

Properties[edit]

The compound is a solid at room temperature, forming colourless 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.

Safety[edit]

Cinnamyl alcohol has been found to have a sensitising effect on some people[3][4] and as a result is the subject of a Restricted Standard issued by IFRA (International Fragrance Association).

Glycosides[edit]

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

References[edit]

  1. ^ "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015. 
  2. ^ Zucca, P; Littarru, M; Rescigno, A; Sanjust, E (May 2009). "Cofactor recycling for selective enzymatic biotransformation of cinnamaldehyde to cinnamyl alcohol". Bioscience, Biotechnology, and Biochemistry. 73 (5): 1224–6. doi:10.1271/bbb.90025. PMID 19420690. 
  3. ^ "Food and Chemical Toxicology" (PDF). RIFM. 2007. 
  4. ^ Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine.
  • Merck Index, 11th Edition, 2305.