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.
Names | |
---|---|
IUPAC name
(2E)-3-phenylprop-2-en-1-ol | |
Other names | |
Identifiers | |
3D model (JSmol) |
|
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.216.224 |
EC Number |
|
KEGG | |
PubChem CID |
|
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). | |
verify (what is ?) | |
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
- Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126
- "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015.
- 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.
- "Food and Chemical Toxicology" (PDF). RIFM. 2007.
- Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine
- Merck Index, 11th Edition, 2305.