verbenol

Verbenol is a term used in natural products and organic chemistry to refer to a group of closely related monoterpene alcohols derived from the verbenyl skeleton. In many contexts, verbenol denotes the allylic alcohol obtained by the reduction of the corresponding verbenone, though the name can also be applied to several stereoisomeric forms sharing the same verbenyl framework. Because multiple stereoisomers exist, verbenol can describe more than one distinct compound.

Occurrence and sources

Verbenol has been identified as a minor constituent in the essential oils of verbena species and other plants in the Verbenaceae family, as well as in related botanical materials. It can also be synthesized chemically for use as a fragrance intermediate or research standard. As with many monoterpene alcohols, verbenol is typically produced in small quantities in nature and more readily obtained via chemical synthesis or hydrogenation of verbenone or related precursors.

Structure and properties

Verbenol comprises a monoterpene skeleton bearing an alcohol functional group. The compound exists in several stereochemical forms due to chiral centers, leading to variations in odor and physical properties among isomers. It is usually a volatile, lipophilic liquid or low-boiling compound, largely insoluble in water and soluble in organic solvents. The olfactory characteristics are generally described as green, fresh, and resinous, depending on the specific isomer.

Preparation and handling

Verbenol can be prepared by catalytic hydrogenation or selective reduction of verbenone and related verbenyl carbonyls. It is isolated from natural sources or produced synthetically, then purified by distillation or chromatographic techniques. Standard safety practices apply, as concentrated samples can be irritant to skin or eyes.

Uses

Verbenol is employed as a fragrance ingredient and a flavor compound in perfumery and食品 applications, and serves as an intermediate in organic synthesis for various terpenoid derivatives. It is typically used in small amounts consistent with other perfume constituents.

See also

Verbenone, monoterpenes, essential oils, fragrance chemistry.