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N-Ethyl-p-menthane-3-carboxamide

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N-Ethyl-p-menthane-3-carboxamide Basic information

Product Name:
N-Ethyl-p-menthane-3-carboxamide
Synonyms:
  • Cooling taste agent ws-23
  • N,2,3-trimethyl-2isopropl butanamide
  • N-Ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide N-Ethyl-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide Ethyl menthane carboxamide Framidice 3 Menthol Carboxamide WS-3
  • FEMA 3455
  • WS-3
  • Menthol Carboxamide
  • N-Ethyl-PARA-Menthan-3-Carboxamide
  • TRPM8 antagonist WS-3
CAS:
39711-79-0
MF:
C13H25NO
MW:
211.34
EINECS:
254-599-0
Mol File:
39711-79-0.mol
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N-Ethyl-p-menthane-3-carboxamide Chemical Properties

Melting point:
87-102 °C
alpha 
D -49 to -54°
Boiling point:
351.04°C (rough estimate)
Density 
0.9305 (rough estimate)
vapor pressure 
0.007Pa at 25℃
refractive index 
1.4410 (estimate)
FEMA 
3455 | N-ETHYL-2-ISOPROPYL-5-METHYLCYCLOHEXANE CARBOXAMIDE
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO: ≥ 100 mg/mL (473.17 mM); Water: < 0.1 mg/mL (insoluble)
pka
16.27±0.60(Predicted)
form 
powder to crystal
color 
White to Almost white
Odor
at 25.00 % in dipropylene glycol. mild mentholic minty
Odor Type
minty
Water Solubility 
insoluble
Merck 
14,3825
JECFA Number
1601
InChIKey
VUNOFAIHSALQQH-UHFFFAOYSA-N
LogP
2.902 at 25℃
CAS DataBase Reference
39711-79-0(CAS DataBase Reference)
EPA Substance Registry System
Cyclohexanecarboxamide, N-ethyl-5-methyl-2-(1-methylethyl)- (39711-79-0)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36-41-22
Safety Statements 
39-26
WGK Germany 
2
HS Code 
29242990
Toxicity
LD50 in mice, rats (g/kg): 5.3, 2.9 orally (Parrish)

MSDS

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N-Ethyl-p-menthane-3-carboxamide Usage And Synthesis

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.

Chemical Properties

Slight menthol-like cooling effect aroma

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

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