Menthyl isovalerate
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Menthyl isovalerate, also known as validolum, is the menthyl
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
of isovaleric acid. It is a transparent oily, colorless liquid with a smell of menthol. It is very slightly soluble in ethanol, while practically insoluble in water. It is used as a
food additive Food additives are substances added to food to preserve Taste, flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), sal ...
for flavor and fragrance. It is produced by typical esterification procedures with usual catalysts such as HCl or H2SO4, and is rather slow, usually done for 20+hr at 100°C or a bit higher. Validol, the anxiety medication containing a roughly 25% solution of menthol in menthyl isovalerate is prepared essentially in one step, in which the amount of menthol added before conducting the acid catalysed esterification is in an excess such that the resulting solution of the yielded ester has around 25% menthol, simplifying the procedure. Work up might consist of several washings, including one with aqueous sodium bicarbonate to neutralize traces of acid catalyst and unreacted isovaleric acid, and distillation.


Medical use

In Poland, Bulgaria, and the former Soviet Union states including Russia, menthyl isovalerate mixed with roughly 25% menthol is sold as an
anxiolytic An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxiet ...
under various trade names including Validol, Valofin, and Menthoval.


See also

*
Methyl pentanoate Methyl pentanoate, commonly known as methyl valerate, is the methyl ester of pentanoic acid (valeric acid) with a fruity odor. Methyl pentanoate is commonly used in fragrances, beauty care, soap, laundry detergents at levels of 0.1–1%. I ...
* Hopantenic acid * Isovaleramide


References

{{GABAAR PAMs GABA analogues GABAA receptor positive allosteric modulators Anxiolytics Sedatives Russian drugs Isovalerate esters Isopropyl compounds