N,2,3-Trimethyl-2-isopropylbutamide
[CAS# 51115-67-4]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N,2,3-Trimethyl-2-isopropylbutamide
• Synonyms: N,2,3-Trimethyl-2-(1-methylethyl)butanamide
• Molecular Formula: C₁₀H₂₁NO
• Molecular Weight: 171.28
• CAS Registry Number: 51115-67-4
• EC Number: 256-974-4
• SMILES: CC(C)C(C)(C(C)C)C(=O)NC

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Melting point: 56-64 °C (Expl.)
• Index of Refraction: 1.431, Calc.^*
• Boiling Point: 233.0±8.0 °C (760 mmHg), Calc.^*
• Flash Point: 132.0±3.4 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

N,2,3-Trimethyl-2-isopropylbutamide, commonly known as WS-23, is a synthetic cooling agent that imparts a cooling sensation without the pungency associated with traditional cooling compounds like menthol. It is widely used in various industries, including food and beverages, cosmetics, and pharmaceuticals, to enhance sensory experiences.

The compound is synthesized through chemical reactions involving specific reagents and conditions. For instance, one method involves the reaction of 2,2-diisopropylpropionitrile with methanol in the presence of an acid catalyst, resulting in the formation of WS-23. This synthetic approach allows for the production of WS-23 in controlled quantities, ensuring consistency and quality for industrial applications.

In the food and beverage industry, WS-23 is utilized as a flavoring agent to provide a cooling effect in products such as candies, beverages, and chewing gums. Its ability to deliver a refreshing sensation without the strong taste of menthol makes it particularly valuable in products where a subtle cooling effect is desired.

In the cosmetic sector, WS-23 is incorporated into products like shampoos, conditioners, lotions, and deodorants to enhance the sensory experience. The cooling effect contributes to a perception of freshness and cleanliness, which is appealing to consumers.

In pharmaceuticals, WS-23 is used in topical formulations to provide a cooling sensation, which can help soothe irritation and discomfort. Its inclusion in creams and ointments enhances patient compliance by improving the sensory attributes of the product.

Regarding safety, evaluations by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) have concluded that WS-23 poses no safety concern when used as a flavoring agent at current levels of intake. The evaluation is conditional upon the estimated daily intake being based on the anticipated annual volume of production.

In summary, N,2,3-Trimethyl-2-isopropylbutamide (WS-23) is a synthetic cooling agent extensively used across various industries to enhance sensory experiences. Its unique ability to provide a cooling effect without the pungency of traditional cooling compounds makes it a valuable ingredient in food, beverages, cosmetics, and pharmaceuticals.

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

2019. Effectiveness of Several Palate Cleansers on Carry-Over Effect of Minty Chewing Gums. Chemosensory Perception.
DOI: 10.1007/s12078-019-09271-x

2016. Delivery of Taste and Aroma Components in Sugar-Free Chewing Gum: Mass Balance Analysis. Chemosensory Perception.
DOI: 10.1007/s12078-016-9218-y