Cinnamyl alcohol
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Names | |
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Preferred IUPAC name (2E)-3-Phenylprop-2-en-1-ol | |
Other names Cinnamyl alcohol Cinnamic alcohol Styryl carbinol Phenylallyl alcohol Styron[2] | |
Identifiers | |
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.216.224 ![]() |
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InChI
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Properties | |
Chemical formula | C9H10O |
Molar mass | 134.178 g·mol−1 |
Density | 1.0397 g/cm3 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 |
-87.2·10−6 cm3/mol | |
Hazards | |
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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). ![]() ![]() ![]() Infobox references |
Cinnamyl alcohol or styron[2] 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 is a occurs naturally only in small quantities, so its industrial demand is usually fulfilled by chemical synthesis starting from cinnamaldehyde.[3]
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[4] and as a deodorant.
Cinnamyl alcohol is the starting material used in the synthesis of reboxetine.[5]
Safety
Cinnamyl alcohol has been found to have a sensitizing effect on some people[6][7] 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
- ^ Merck Index, 11th Edition, 2305
- ^ a b Chemical News and Journal of Industrial Science, Volumes 27-28, Sir William Crookes, page 126
- ^ 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.
- ^ "cinnamyl alcohol 104-54-1". thegoodscentscompany.com. Retrieved 26 July 2015.
- ^ "Reboxetine mesilate".
- ^ "Food and Chemical Toxicology" (PDF). RIFM. 2007. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.
- ^ Survey and health assessment of chemical substances in massage oils Archived 2007-06-28 at the Wayback Machine