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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
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.216.224 Edit this at Wikidata
EC Number
  • 203-212-3
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+Key: OOCCDEMITAIZTP-QPJJXVBHSA-N
  • InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+Key: OOCCDEMITAIZTP-QPJJXVBHBG
SMILES
  • c1ccc(cc1)/C=C/CO
Properties
Chemical formula C9H10O
Molar mass 134.178 g·mol
Density 1.0397 g/cm at 35 °C
Melting point 33 °C (91 °F; 306 K)
Boiling point 250 °C (482 °F; 523 K)
Solubility in water Slightly
Solubility soluble in ethanol, acetone, dichloromethane
Magnetic susceptibility (χ) -87.2·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H317
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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

  1. Merck Index, 11th Edition, 2305
  2. ^ Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126
  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. "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015.
  5. "Reboxetine mesilate".
  6. "Food and Chemical Toxicology" (PDF). RIFM. 2007. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.
  7. Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine
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