Cooling Agent Ws-3
Cooling agent WS-3 is N-ethyl-p-menthane-3-carboxamide, a synthetic terpene carboxamide that produces a cooling sensation without the aroma load of menthol. It carries FEMA number 3455 and is registered under CAS number 39711-79-0. It was the first of the Wilkinson Sword series of coolers to reach wide commercial use, and it remains the reference material against which newer coolers are compared.
Like menthol it acts as an agonist at TRPM8, the cold sensitive ion channel on trigeminal and sensory nerve endings, but because the aroma bearing hydroxyl group of menthol has been replaced by an amide, the cooling can be delivered at a level that would be intolerably minty if menthol were used. WS-3 gives a fast onset and a strong initial impact that fades more quickly than the aliphatic coolers, and it retains a faint minty and slightly bitter character that formulators either use deliberately in mint products or blend away in fruit ones. It is frequently combined with slower, longer lasting coolers to give a single continuous effect.
The material is a white crystalline powder melting in the low seventies of degrees Celsius. It dissolves readily in ethanol, propylene glycol, triacetin and oils and only sparingly in water, so aqueous systems are dosed with a carrier solution rather than the neat solid.
We source bulk Cooling Agent Ws-3 from top China manufacturers for our partners. The manufacturers are mostly in Anhui. A smaller requirement can ship in a combined container with other ingredients.
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- Function
- Flavours and Aromas
Specifications
| Item | Specification |
|---|---|
| Appearance | White crystalline powder |
| Odour | Very faint, slightly minty |
| Taste Effect | Rapid onset cooling, matching reference intensity |
| Assay by GC | Not less than 99.0 percent |
| Identification | Infrared and mass spectra conform to reference |
| Melting Range | 68 to 78 °C depending on isomer ratio |
| Optical Rotation | Within the range declared for the grade |
| Loss on Drying | Not more than 0.5 percent |
| Residue on Ignition | Not more than 0.1 percent |
| Related Substances | Any single impurity not more than 0.5 percent |
| Residual Solvent | Within the applicable limits for the solvents used |
| Solubility | Freely soluble in ethanol and propylene glycol, slightly soluble in water |
| Heavy Metals (as Pb) | Not more than 10 mg/kg |
| Lead | Not more than 2 mg/kg |
| Arsenic | Not more than 1 mg/kg |
Common Markets Grades
WS-3 is a single defined substance, so the axes are purity, isomeric composition, physical form and carrier. Flavour and food grade material is offered at not less than ninety eight or ninety nine percent by gas chromatography. Because the p-menthane ring carries several stereocentres, the isomer distribution differs according to the terpene feedstock and the route used, and buyers specify optical rotation alongside assay since the cooling potency of the isomers is not equal.
Presentation covers crystalline solid, milled powder to a stated mesh, and ready made solutions at typically ten to fifty percent in propylene glycol, triacetin, ethanol or medium chain triglyceride, which are widely used because melting or dissolving the solid in a plant is awkward. Encapsulated and spray dried grades on maltodextrin, gum acacia or a fat matrix are used for chewing gum, compressed tablets and dry mixes, where the aim is controlled release rather than solubility. Separate specifications exist for oral care and personal care use, where the material is bought under its INCI name, and for vapour and tobacco applications, where residual solvent limits are tighter.
Applications
- Chewing gum, where fast onset cooling reinforces the initial mint impact
- Toothpaste, mouthwash and breath films, boosting cooling above what menthol alone can give
- Mints, lozenges and compressed tablets
- Menthol cigarettes, capsules and oral nicotine pouches
- Electronic cigarette liquids, alone or blended with slower coolers
- Carbonated soft drinks and flavoured waters, at low dosage for a refreshing finish
- Fruit confectionery, where cooling is wanted without a mint aroma
- Aftershave, shaving gel and facial care, for immediate cooling on application
- Shampoo and scalp treatments, where the effect is associated with cleansing
- Topical muscle rubs and sports gels, in combination with other counterirritants
China Manufacturers of Cooling Agent Ws-3
Top Cooling Agent Ws-3 manufacturers in China.
- Anhui Ever-developing Perfume Co., Ltd.5 ingredients in the directory
Anhui Tonghui Perfume Co., Ltd.8 ingredients in the directory
Company names and logos are the property of the manufacturers themselves. They are listed here because our own directory records them as producing this ingredient. A listing is not an endorsement by them, and we do not represent them or speak on their behalf.
Regulatory Status
In the United States WS-3 is used as a flavouring substance and holds FEMA GRAS status under FEMA number 3455, which is the basis for its use in food, beverage and chewing gum. Use in toothpaste, mouthwash and other oral care and personal care products sits outside the food framework and is governed by the cosmetic provisions of the Federal Food, Drug, and Cosmetic Act, or by the applicable over the counter monograph where a therapeutic claim is made. Use in tobacco and vapour products is regulated separately by the Centre for Tobacco Products.
In the European Union, Regulation (EC) No 1334/2008 treats carboxamide cooling agents as flavouring substances, and a formulator must confirm that the specific substance is present in the Union list of authorised flavouring substances for the intended category before use, since the list does not carry every cooling agent in commerce. Flavouring substances carry no E number, though carriers and solvents blended with them are additives or processing aids in their own right. In cosmetic use the substance falls under Regulation (EC) No 1223/2009 and is declared by INCI name. Codex covers flavourings through its general guidelines for their use, and international expert evaluation of the cooling agents has proceeded through the flavouring substance programmes rather than as additive assessment.
Manufacturing Process
WS-3 is made by synthesis from a terpene feedstock. The key intermediate is p-menthane-3-carboxylic acid, which is produced from terpene raw materials in the menthol and turpentine chain, with the reaction conditions and the starting isomer determining the ratio of ring isomers carried through into the finished cooler. The crude acid is purified by distillation or by crystallisation of a salt, and the isomer ratio is checked at this stage because it cannot be corrected later.
The purified acid is converted to its acid chloride with thionyl chloride under reflux, and the hydrogen chloride and sulphur dioxide evolved are taken to a caustic scrubber while excess reagent is stripped under vacuum. The acid chloride is condensed with ethylamine, added as an aqueous solution or as the gas, under Schotten-Baumann conditions with alkali present to neutralise the acid liberated, and the mixture is held cold to suppress hydrolysis. The crude amide is washed with dilute acid to remove residual amine and then with alkali and water, the solvent is recovered by distillation, and the product is recrystallised from a hydrocarbon or alcohol solvent. The crystals are centrifuged, dried under vacuum well below the melting point, milled to the ordered mesh and packed in lined drums. Release testing covers assay, related substances, optical rotation, melting range, residual solvent and heavy metals, supported by a sensory check of cooling intensity against a reference.
