N-Ethyl-p-menthane-3-carboxamide
[CAS# 39711-79-0]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-Ethyl-p-menthane-3-carboxamide
• Synonyms: N-Ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide; N-Ethyl-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide
• Molecular Formula: C₁₃H₂₅NO
• Molecular Weight: 211.35
• CAS Registry Number: 39711-79-0
• EC Number: 254-599-0
• FEMA: 3455
• SMILES: CCNC(=O)C1CC(CCC1C(C)C)C

Properties

• Solubility: insoluble (water), 100mM (DMSO) (Expl.)
• Density: 0.9±0.1 g/cm³, Calc.^*
• Melting point: 87-102 °C
• Index of Refraction: 1.454, Calc.^*
• Boiling Point: 340.5±9.0 °C (760 mmHg), Calc.^*
• Flash Point: 205.7±3.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H319
• Safety Statements: P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

N-Ethyl-p-menthane-3-carboxamide, commonly known as menthyl ethylcarbamate, is a synthetic derivative of menthol. It is used primarily for its cooling and soothing properties in various applications, including in cosmetics, personal care products, and food items. The compound is known for its ability to provide a mild, long-lasting cooling effect on the skin and mucous membranes, making it a popular ingredient in many topical formulations.

The discovery of N-ethyl-p-menthane-3-carboxamide is linked to the broader study of menthol derivatives, which have been explored for their cooling and aromatic properties. Menthol itself, a naturally occurring compound found in mint oils, has been used for centuries for its therapeutic and flavoring properties. The development of N-ethyl-p-menthane-3-carboxamide was part of an effort to modify menthol and enhance its sensory effects, leading to a more sustained cooling sensation without the sharp intensity that pure menthol can sometimes produce.

In the personal care industry, N-ethyl-p-menthane-3-carboxamide is valued for its mild and non-irritating cooling effects. It is commonly used in products such as lotions, creams, shampoos, and deodorants, where it provides a refreshing and soothing sensation. The compound’s cooling effect makes it especially popular in products designed to relieve skin irritation or after-sun care, as it offers a gentle alternative to more intense cooling agents like menthol. Its inclusion in such formulations is often intended to provide a relaxing and rejuvenating experience for the user.

In the food and beverage industry, N-ethyl-p-menthane-3-carboxamide is used as a flavoring agent to impart a refreshing minty taste and cooling sensation. It is favored for its smoother and less intense flavor profile compared to menthol, making it suitable for a wider range of products, including gums, candies, and beverages. The compound’s mild effect makes it an attractive option for use in consumer products where a more subtle mint flavor is desired.

N-Ethyl-p-menthane-3-carboxamide is also found in oral care products, such as toothpaste and mouthwashes. Its inclusion helps to provide a refreshing taste and cooling sensation, enhancing the overall sensory experience of the product. Additionally, it serves to mask unpleasant flavors in oral care products while contributing to a clean and invigorating feeling after use.

In conclusion, N-ethyl-p-menthane-3-carboxamide is a synthetic compound with significant applications in the cosmetics, food, and pharmaceutical industries. Its cooling and soothing properties, along with its milder and longer-lasting effects compared to menthol, make it a valuable ingredient in various consumer products designed to refresh, soothe, and enhance sensory experiences.

References

2024. Refreshing Perception of Foods and Beverages and Related Health Benefits. Flavor-Associated Applications in Health and Wellness Food Products.
DOI: 10.1007/978-3-031-51808-9_16

2020. E. Springer Lexikon Kosmetik und Körperpflege.
DOI: 10.1007/978-3-662-59127-7_5

2016. Chemical Activation of Sensory TRP Channels. Topics in Medicinal Chemistry.
DOI: 10.1007/7355_2015_98