Menthyl PCA

Menthyl PCA

Product Name Menthyl PCA
Other Names Menthyl pyrrolidone carboxylate; L-Menthyl PCA; Menthyl 2-pyrrolidone-5-carboxylate
CAS Number 64519-82-0
Molecular Formula C14H25NO3
Molecular Weight 255.35 g/mol
Appearance Colorless to pale yellow clear liquid
Assay (GC) ≥98.0%
Specific Rotation [α]D20 −45° to −55° (neat)
Refractive Index 1.465–1.475 (20 °C)
Solubility Soluble in ethanol, propylene glycol, and most cosmetic esters; sparingly soluble in water
Package 25 kg net in HDPE drum, or 200 kg net in steel drum

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Menthyl PCA Structure

Synonyms: Menthyl pyrrolidone carboxylate, L-Menthyl PCA, Menthyl 2-pyrrolidone-5-carboxylate, PCA menthyl ester, N-Menthyl-2-pyrrolidone-5-carboxylate

Menthyl PCA is the menthyl ester of pyrrolidone carboxylic acid (PCA), a cyclic lactam that occurs naturally as a major component of the skin’s natural moisturizing factor (NMF). The molecule pairs a lipophilic menthyl head with a polar PCA moiety, a structural arrangement that gives it a dual profile: mild cooling on application and a lasting humectant effect. Unlike menthol, it does not rely on TRPM8 activation alone; its cooling is perceived as smooth and gradual, with minimal odor and no sting.

Commercially, Menthyl PCA is produced by esterifying L-menthol with PCA or its derivatives under controlled conditions, yielding a high-purity liquid that is miscible with common cosmetic and pharmaceutical carriers. It is supplied as a technical grade for industrial formulation and is used where a balanced sensory experience—cooling plus moisturization—is desired without the volatility and irritation often associated with free menthol.

Formulators working on skin care, sun care, after-sun, and topical analgesics value Menthyl PCA for its ability to deliver a refreshing feel while supporting the skin’s own hydration system. It also finds use in oral care and confectionery, where a clean, non-bitter cooling profile is critical. The material is typically used at 0.5–5% depending on the application, and its compatibility with a wide range of emollients and surfactants makes it easy to incorporate into both anhydrous and emulsion systems.

Chemical Structure & Properties

Menthyl PCA (C14H25NO3) is a chiral ester built from L-menthol and pyrrolidone carboxylic acid. The menthyl group contributes a bulky, lipophilic cyclohexyl ring with three stereocenters, while the PCA portion introduces a polar lactam ring that can participate in hydrogen bonding. This amphiphilic character explains its solubility profile: it disperses readily in ethanol, glycols, and cosmetic esters, yet remains only sparingly soluble in water. The ester linkage is stable under normal storage conditions but can hydrolyze under strongly acidic or basic conditions, so formulators should avoid extreme pH. The material is a clear, mobile liquid at room temperature, with a faint, characteristic menthol-like odor that is far milder than that of menthol itself.

Mechanism of Action

  • TRPM8 activation: Menthyl PCA interacts with the cold-sensing TRPM8 receptor, triggering a cooling sensation that is perceived as gentle and sustained rather than sharp.
  • Humectant activity: The PCA moiety binds water and helps reinforce the skin’s natural moisturizing factor, improving hydration and barrier function.
  • Reduced irritation potential: Compared with menthol, the esterified form is less volatile and less likely to cause stinging or redness, making it suitable for sensitive skin applications.
  • Formulation synergy: It can be combined with other cooling agents (e.g., WS-23, menthyl lactate) to modulate intensity and duration without overwhelming the sensory profile.

Quality Specifications

Parameter Specification
Assay (GC) ≥98.0%
Appearance Colorless to pale yellow clear liquid
Specific Rotation [α]D20 −45° to −55° (neat)
Refractive Index 1.465–1.475 (20 °C)
Heavy Metals ≤10 ppm
Water Content ≤0.5% (Karl Fischer)

Supply & Documentation

  • Capacity: 5 MT per month, with scale-up available for long-term contracts.
  • Lead time: 3-5 business days (stock items)
  • Documentation: COA, MSDS, TDS, and regulatory support (REACH, FDA, etc.) provided upon request.
  • Packaging: 25 kg HDPE drums or 200 kg steel drums, with custom packaging available.

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