Cinnamyl alcohol or styron is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

that is found in

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

ified form in

storax Storax (; , ''stúrax''), often commercially sold as styrax, is a natural fragrant resin isolated from the wounded bark of ''Liquidambar orientalis'' Mill. (Asia Minor) and ''Liquidambar styraciflua'' L. (Eastern US, Mexico, Central America) (A ...

Balsam of Peru Balsam is the resinous exudate (or sap) which forms on certain kinds of trees and shrubs. Balsam (from Latin ''balsamum'' "gum of the balsam tree," ultimately from a Semitic source such as ) owes its name to the biblical Balm of Gilead. Chem ...

, and

cinnamon Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, biscuits, b ...

leaves. It forms a white crystalline solid when pure, or a yellow oil when even slightly impure. It can be produced by the

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of storax. Cinnamyl alcohol occurs naturally only in small quantities, so its industrial demand is usually fulfilled by chemical synthesis starting from

cinnamaldehyde Cinnamaldehyde is an organic compound with the formula or . Occurring naturally as predominantly the ''trans'' (''E'') isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway ...

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 In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...

, 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 ''Hyacinthus'' is a genus of bulbous herbs, and spring-blooming Perennial plant, perennials. They are fragrant flowering plants in the family Asparagaceae, subfamily Scilloideae and are commonly called hyacinths (). The genus is native predomin ...

, 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 Reboxetine, sold under the brand name Edronax among others, is a selective norepinephrine reuptake inhibitor (sNRI) medication marketed as an antidepressant by Pfizer for use in the treatment of major depressive disorder, although it has also be ...

Safety

Cinnamyl alcohol has been found to have a

sensitizing Sensitization is a non-associative learning process in which repeated administration of a stimulus results in the progressive amplification of a response. Sensitization often is characterized by an enhancement of response to a whole class of st ...

effect on some peopleSurvey and health assessment of chemical substances in massage oils
and as a result is the subject of
Restricted Standard
issued b
IFRA
( International Fragrance Association).

Glycosides

Rosarin and rosavin are cinnamyl alcohol glycosides isolated from ''

Rhodiola rosea ''Rhodiola rosea'' (commonly golden root, rose root, roseroot, Aaron's rod, Arctic root, king's crown, ''lignum rhodium'', orpin rose) is a perennial plant, perennial flowering plant in the family Crassulaceae. It grows naturally in wild Arctic ...

''.

References

{{Authority control Flavors Primary alcohols Phenylpropanoids Perfume ingredients