3825. Ethyl Menthane Carboxamide

Nomenclature

CAS number: 39711-79-0
N-Ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide; N-ethyl-4-menthane-3-carboxamide; WS3.
C13H25NO; mol wt 211.34.
C 73.88%, H 11.92%, N 6.63%, O 7.57%.

Description and references

Prepn: NL 7201523; H. R. Watson et al., US 4193936 (1972, 1980 both to Wilkinson Sword). Structure-activity study: H. R. Watson et al., J. Soc. Cosmet. Chem. 29, 185 (1978). Brief review: M. A. Parrish, Manuf. Chem. 58, 31-32 (February, 1987).

Chemical structure

Properties

White to nearly white powder, mp 88°. [α]D -49 to -54°. Insol in water. Sol in most organic solvents. Average oral cooling threshold: 0.2 μg. LD50 in mice, rats (g/kg): 5.3, 2.9 orally (Parrish).

Use

Physiological coolant in foods, beverages, toiletries, cosmetics and pharmaceuticals.