(1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide (CAS 68489-09-08) — Citrus Non-volatile Note Fragrance Ingredient
(1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
CAS 68489-09-08
What Is (1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide?
(1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide is a synthetic cooling agent used in chewing gums, oral care products, and some fragrances. It creates a strong cooling sensation similar to menthol but without the minty odor. This ingredient matters because it provides long-lasting cooling effects in products where traditional cooling agents like menthol might interfere with flavor or fragrance profiles.
Safety Profile
USE WITH AWARENESSWhat Does (1R,2S,5R)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide Smell Like?
This synthetic cooling agent is virtually odorless, making it ideal for applications where scent neutrality is desired. The compound produces an intense, clean cooling sensation that builds gradually on application, peaking within minutes and lasting significantly longer than traditional cooling agents. Unlike menthol, there’s no accompanying minty or camphoraceous aroma, allowing it to blend seamlessly into any fragrance composition without altering the olfactory profile.
Chemistry, Properties & Perfumer Guide
The Chemistry
This chiral carboxamide belongs to the class of non-volatile cooling agents, structurally related to WS-23 and WS-3. The (1R,2S,5R) stereochemistry is crucial for its cooling properties. It’s synthesized through stereoselective reactions involving isopulegol derivatives and p-anisidine. The methoxy group on the phenyl ring enhances the molecule’s binding to TRPM8 receptors, responsible for cold sensation, while the bulky isopropyl group contributes to its prolonged effect duration.
Physical & Chemical Properties
| Appearance | White crystalline powder |
|---|---|
| Melting Point | 92-94 °C |
Perfumer Guide
| Application | Typical % | Range | Notes |
|---|---|---|---|
| Chewing Gum | 0.1-0.5% | Up to 1% | Provides long-lasting cooling |
| Oral Care | 0.05-0.2% | Up to 0.5% | Scent-free cooling |
| Fine Fragrance | 0.01-0.1% | Up to 0.3% | Cooling skin effect |
Classic Accords
Tip: Use in conjunction with traditional cooling agents to create multi-dimensional cooling effects without scent interference.
Alternatives & Comparisons
More potent cooling agent with similar odorless properties, but shorter duration of action.
Safety, Regulatory & Sustainability
⚠ Regulatory Disclaimer
General reference only. Consult current IFRA Standards Library before formulating.
IFRA Status
Not currently restricted by IFRA.
GHS Classification
RIFM Assessment
RIFM has reviewed safety data and established acceptable use levels for cosmetic applications.
Sustainability
As a synthetic compound, this cooling agent is produced through controlled chemical synthesis, avoiding agricultural resource use. The production process has been optimized to minimize waste and energy consumption. Unlike some natural cooling agents, it doesn’t rely on mint crop cultivation, reducing land use impact.
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