Cinnamyl alcohol

Cinnamyl alcohol or styron[1] 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
Names
IUPAC name
(2E)-3-phenylprop-2-en-1-ol
Other names
Cinnamyl alcohol
Cinnamic alcohol
Styryl carbinol
Phenylallyl alcohol
Styron[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.216.224
EC Number
  • 203-212-3
KEGG
UNII
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
GHS pictograms
GHS Signal word Warning
H317
P261, P272, P280, P302+352, P321, P333+313, P363, P501
Flash point 126°C
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 has a distinctive odour described as "sweet, balsam, hyacinth, spicy, green, powdery, cinnamic" and is used in perfumery[2] 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.[3]

Properties

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

Cinnamyl alcohol has been found to have a sensitising effect on some people[4][5] 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

  1. Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126
  2. "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015.
  3. 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.
  4. "Food and Chemical Toxicology" (PDF). RIFM. 2007.
  5. Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine
  • Merck Index, 11th Edition, 2305.
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