Chemical Properties
Benzyl mercaptan has repulsive, garlic-like odor. It oxidizes in air to dibenzyl disulfide.
Chemical Properties
Cream to white, moist crystals; musty
odor. Insoluble in water; soluble in alcohol
or ether. There are three isomers with different
boiling points.
Occurrence
Reported found in coffee.
Definition
ChEBI: Benzyl thiol is a thiol that is toluene in which one of the methyl hydrogens has been replaced by a sulfanyl group. It has a role as a plant metabolite. It is a thiol and a member of benzenes. It derives from a hydride of a toluene.
Preparation
From benzyl chloride and potassium hydrosulfide.
Aroma threshold values
Detection: 0.19 to 2.6 ppb.
Taste threshold values
Taste characteristics at 15 ppm: leek, horseradish, cabbage, green, tomato and coffee.
Purification Methods
Purify benzyl mercaptan via the mercury salt [see Kern J Am Chem Soc 75 1865 1953], which crystallises from *benzene as needles (m 121o), and then dissolve it in CHCl3. Pass H2S gas through the solution to regenerate the mercaptan. The HgS that precipitates is filtered off and washed thoroughly with CHCl3. The filtrate and washings are evaporated to remove CHCl3; then the residue is fractionally distilled under reduced pressure [Mackle & McClean, Trans Faraday Soc 58 895 1962]. [Beilstein 6 IV 2632.]
