Cinnamyl alcohol

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Cinnamyl alcohol
Skeletal formula
A sample of cinnamyl alcohol on a petri dish.
Names
Preferred 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 Edit this at Wikidata
EC Number
  • 203-212-3
KEGG
UNII
  • InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+ checkY
    Key: OOCCDEMITAIZTP-QPJJXVBHSA-N checkY
  • InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
    Key: OOCCDEMITAIZTP-QPJJXVBHBG
  • c1ccc(cc1)/C=C/CO
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
GHS labelling:
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
Flash point 126°C
Safety data sheet (SDS) 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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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 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. ^ a b 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. S2CID 28741979.
  4. ^ "Food and Chemical Toxicology" (PDF). RIFM. 2007. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.
  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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