Occurrence:
Menthol is monoterpene alcohol found in mint oil or peppermint oil.
The sources of mint oil are Mentha piperita Var. vulgaris, Mentha piperita Var. officinalis, Mentha arvensis, Mentha canadensis Var. piperascence
Family: Piperaceae.
1 to 3 % volatile oil is present in peppermint.
The two varieties Mentha piperita Var. vulgaris and Mentha piperita Var. officinalis contains not less than 45 % of menthol whereas the varieties Mentha arvensis and Mentha canadensis Var. piperascence contains upto 70 to 90 % of menthol.
The other constituents are (+) neomenthol, (+) isomenthol, menthofuran, menthone, menthyl acetate and cineole.
Menthol can be synthesized chemically by hydrogenation of thymol.
(-)-l-Menthol
(+)- d- Menthol
Isolation:
Mentha oil is obtained by hydrodistillation and steam distillation of fresh parts of the mentha plant.
For the isolation of (-) menthol from peppermint oil, the oil is subjected to cooling.
The menthol crystal crystallizes out and is separated by centrifugation.
The corn mint oil is obtained from steam distillation of Mentha arvensis flowering tops which contains about 70 to 80 percent of free (-) menthol.
The oil is cooled and menthol crystals are separated by centrifugation.
Pure (-) menthol is obtained from recrystallisation from low boiling solvents.
The Melting point of menthol is 41 to 44°C.
Thin layer chromatography of Menthol:
1 mg menthol is dissolved in 1 ml of methanol.
Then apply a spot on silica gel-G plate and elute it in chloroform.
The dried plates are sprayed with 1 percent vanillin-sulphuric acid reagent.
Heat the plate at 110°C for 10 minutes.
The Rf value of menthol is 0.48 to 0.62.
Identification
A few drops of menthol mixed with 5ml nitric acid solution (prepared by adding 1ml nitric acid to 300ml glacial acetic acid) are heated on a water bath. Within 5 minutes, a blue colour develops which deepens on further heating and produces copper colour fluorescence that turns golden yellow after some time.
Where, a and b = Titration volumes (ml) of 0.5mol/lml of hydrochloric acid added to acetylated oil and un-acetylated oil, respectively. c = Titration volume (ml) of hydrochloric acid used in the blank test.