Cinnamyl alcohol
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| Preferred IUPAC name
(2E)-3-Phenylprop-2-en-1-ol | |
| Other names | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.216.224 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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) |
| Slightly | |
| Solubility | soluble in ethanol, acetone, dichloromethane |
| −87.2·10−6 cm3/mol | |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H317 | |
| P261, P272, P280, P302+P352, P321, P333+P313, P363, P501 | |
| Flash point | 126 °C (259 °F; 399 K) |
| 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 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]
There is basic medical research investigating the neuroprotective properties of cinnamyl alcohol in terms of the following with respect to epilepsy:[6]
- Potentiating the GABAergic system
- Promoting antioxidant effects
- Reducing pro-inflammatory mediators activities.
Safety
Cinnamyl alcohol has been found to have a sensitizing effect on some people[7][8] 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.