Menthyl isovalerate

Menthyl isovalerate
Names
IUPAC name
(1R,3R,4S)-p-Menthan-3-yl 3-methylbutanoate
Systematic IUPAC name
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoate
Other names
Validolum; Valofin; Validol; Menthoval
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.036.766 Edit this at Wikidata
UNII
  • InChI=1S/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1
    Key: VYQSSWZYPCCBRN-HZSPNIEDSA-N
  • InChI=1/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1
    Key: VYQSSWZYPCCBRN-HZSPNIEDBT
  • C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)CC(C)C)C(C)C
Properties
C15H28O2
Molar mass 240.387 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Menthyl isovalerate, also known as validolum, is the menthyl ester 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 for flavor and fragrance.[1]

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.[citation needed]

  1. ^ Menthyl isovalerate.