Chemical Properties
Slight menthol-like cooling effect aroma
Chemical Properties
white crystalline powder
Chemical Properties
N-ethyl-p-menthane-3-carboxamide is an odorless white, crystalline
solid. The compound has a strong and clear physiological cooling effect
and is used mainly in oral care products.
Uses
WS 3 is a selective transient receptor potential melastatin-8 ligand.
Uses
Physiological coolant in foods, beverages, toiletries, cosmetics and pharmaceuticals.
Definition
ChEBI: Ethyl menthane carboxamide is a p-menthane monoterpenoid.
Aroma threshold values
Aroma characteristics at 1.0%. Virtually odorless
Taste threshold values
Taste characteristics at 10 to 100 ppm. Intense lingering cooling. The cooling sensation builds slow but
steadily and grows to a lingering cooling mouthfeel with a slightly camphoraceous and minty character.
Flammability and Explosibility
Not classified
Trade name
Winsense WS-3 (Renessenz)
Biological Activity
Cooling agent that is an agonist at TRPM8 receptors (EC 50 = 3.7 μ M).
Synthesis
0.89
g (0.0091 mol) of polyphosphoric acid (85%) and 0.42 g (0.0091 mol) of
ethanol were weighed. 0.54 g (0.0046 mol) of diethylcarbonate was added
dropwise slowly while cooling in an ice bath, wherein the temperature
increases slightly. After about 5 minutes, 0.5 g (0.0030 mol) of
p-menthane-3-carbonitrile was added. The reaction solution was heated
and stirred for 102 hours at 150??C. At the end of the reaction by GC,
about 70% of desired N-Ethyl-p-menthane-3-carboxamide was formed.
Fig The synthetic method 1 of N-Ethyl-p-menthane-3-carboxamide
