39711-79-0

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;n-ethyl-5-methyl-2-(1-methylethyl)-cyclohexanecarboxamid;TIMTEC-BB SBB008527;N-ETHYL-5-METHYL-2-(1-METHYLETHYL)-CYCLOHEXANE-CARBOXAMIDE
• CAS NO: 39711-79-0
• Molecular Formula: C₁₃H₂₅NO
• Molecular Weight: 211.34
• EINECS: 254-599-0
• Mol File: 39711-79-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 87-102 °C
• Boiling Point: 351.04°C (rough estimate)
• Flash Point: 205.7 °C
• Appearance: white crystalline powder
• Density: 0.9305 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4410 (estimate)
• Storage Temp.: Store at RT
• PKA: 16.27±0.60(Predicted)
• Water Solubility: insoluble
• Merck: 14,3825
• CAS DataBase Reference: N-Ethyl-p-menthane-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethyl-p-menthane-3-carboxamide(39711-79-0)
• EPA Substance Registry System: N-Ethyl-p-menthane-3-carboxamide(39711-79-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36-41-22
• Safety Statements: 39-26
• WGK Germany: 2
• Hazardous Substances Data: 39711-79-0(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 39711-79-0 differently. You can refer to the following data:
1. white crystalline powder
2. 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.
3. Slight menthol-like cooling effect aroma

Uses

Different sources of media describe the Uses of 39711-79-0 differently. You can refer to the following data:
1. WS 3 is a selective transient receptor potential melastatin-8 ligand.
2. Physiological coolant in foods, beverages, toiletries, cosmetics and pharmaceuticals.

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

Notclassified

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

InChI:InChI=1/C13H25NO/c1-5-14-13(15)12-8-10(4)6-7-11(12)9(2)3/h9-12H,5-8H2,1-4H3,(H,14,15)/t10-,11+,12+/m0/s1

Synthetic route

WS-3 (39711-79-0) → menthanecarboxylic acid (39668-86-5)

Conditions	Yield
With sulfuric acid; water; sodium nitrite at 75℃;	61%

Downstream Products

• 39668-86-5 menthanecarboxylic acid 

Relevant articles and documents

Composition having insect repellent characteristics

The present invention relates to a composition having effective insect repellent characteristics comprising as an active ingredient an N-substituted p-menthane carboxamide, which has little or no odor and which is substantially non-toxic for human, pet and livestock.