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
GHS hazard statements
 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.

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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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