Cooling Agent WS-3

Synonyme: N-Ethyl-p-menthane-3-carboxamide, WS-3, Cooling Agent 3, N-Ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide, Menthane carboxamide, N-Ethyl-p-menthyl-3-carboxamide

Cooling Agent WS-3 is a synthetic cyclohexane carboxamide derivative, structurally characterized by a p-menthane ring system bearing an N-ethyl carboxamide moiety. This lipophilic compound interacts selectively with the cold-sensitive TRPM8 ion channel, producing a sustained cooling sensation without the characteristic minty odor or flavor of menthol. Its molecular design incorporates a bulky isopropyl group at the 2-position and a carboxamide at the 3-position, which together confer high receptor affinity and metabolic stability.

WS-3 is manufactured through a multi-step synthesis starting from p-menthane-3-carboxylic acid, followed by amidation with ethylamine. The process yields a high-purity crystalline solid that is standardized to ≥99% by HPLC. Unlike natural menthol, WS-3 is non-volatile and odorless, making it ideal for applications where flavor neutrality and prolonged cooling are required. It is supplied in various particle sizes to suit different formulation needs.

In the B2B arena, WS-3 finds extensive use in oral care products, confectionery, topical analgesics, and functional beverages. Its ability to deliver a clean, long-lasting cooling effect at low concentrations (typically 0.05–0.5%) has made it a preferred choice for formulators seeking to enhance sensory appeal without the drawbacks of menthol. Ongoing research explores its potential in transdermal delivery systems and as a sensory marker in consumer products.

Chemical Structure & Properties

WS-3 features a cyclohexane ring with an isopropyl group at position 2 and an N-ethyl carboxamide at position 3. This arrangement creates a rigid, lipophilic molecule that readily partitions into lipid bilayers. The compound is a white crystalline powder with a melting range of 87–102°C, practically insoluble in water but freely soluble in ethanol and propylene glycol. Its logP value of approximately 3.2 indicates moderate lipophilicity, which facilitates skin penetration and interaction with TRPM8.

Mechanism of Action

• TRPM8 activation: WS-3 binds to the TRPM8 receptor on sensory neurons, triggering a cooling sensation without actual temperature change.
• Desensitization of TRPV1: It indirectly reduces capsaicin-induced irritation, providing a soothing effect in topical applications.
• Prolonged effect: Due to its non-volatile nature, WS-3 remains active on the skin or mucosa for extended periods, unlike menthol.
• Synergistic cooling: When combined with other cooling agents (e.g., WS-23), it enhances the overall cooling intensity and duration.
• Low irritation potential: WS-3 exhibits minimal cytotoxicity and is well-tolerated in cosmetic and oral formulations.

Quality Specifications

Supply & Documentation

• Capacity: 50 metric tons per year
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS, and regulatory support available upon request
• Verpackung: 25 kg fiber drum with double PE liners, or as per customer requirements
• Lagerung: Store in a cool, dry place away from direct sunlight

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com