N-Ethyl-p-menthane-3-carboxamide

N-Ethyl-p-menthane-3-carboxamide Basic information
Product Name:N-Ethyl-p-menthane-3-carboxamide
Synonyms:Cooling taste agent ws-23;N,2,3-trimethyl-2isopropl butanamide;N-Ethyl-2-(isopropyl)-5-methylcyclohexanecarboxamide N-Ethyl-5-methyl-2-(1-methylethyl)-cyclohexane-carboxamide Ethyl menthane carboxamide Framidice 3 Menthol Carboxamide WS-3;FEMA 3455;WS-3;Menthol Carboxamide;N-Ethyl-PARA-Menthan-3-Carboxamide;TRPM8 antagonist WS-3
CAS:39711-79-0
MF:C13H25NO
MW:211.34
EINECS:254-599-0
Product Categories:
Mol File:39711-79-0.mol
N-Ethyl-p-menthane-3-carboxamide Structure
N-Ethyl-p-menthane-3-carboxamide Chemical Properties
Melting point 87-102 °C
alpha D -49 to -54°
Boiling point 351.04°C (rough estimate)
density 0.9305 (rough estimate)
vapor pressure 0.007Pa at 25℃
FEMA 3455 | N-ETHYL-2-ISOPROPYL-5-METHYLCYCLOHEXANE CARBOXAMIDE
refractive index 1.4410 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility DMSO: ≥ 100 mg/mL (473.17 mM); Water: < 0.1 mg/mL (insoluble)
pka16.27±0.60(Predicted)
form powder to crystal
color White to Almost white
Odorat 25.00 % in dipropylene glycol. mild mentholic minty
Odor Typeminty
Water Solubility insoluble
Merck 14,3825
JECFA Number1601
InChIKeyVUNOFAIHSALQQH-UHFFFAOYSA-N
LogP2.902 at 25℃
CAS DataBase Reference39711-79-0(CAS DataBase Reference)
EPA Substance Registry SystemCyclohexanecarboxamide, N-ethyl-5-methyl-2-(1-methylethyl)- (39711-79-0)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36-41-22
Safety Statements 39-26
WGK Germany 2
HS Code 29242990
ToxicityLD50 in mice, rats (g/kg): 5.3, 2.9 orally (Parrish)
MSDS Information
ProviderLanguage
N-Ethyl-p-menthane-3-carboxamide English
ACROS English
N-Ethyl-p-menthane-3-carboxamide Usage And Synthesis
Chemical Propertieswhite crystalline powder
Chemical PropertiesN-ethyl-p-menthane-3-carboxamide is an odorless white, crystalline solid. The compound has a strong and clear physiological cooling effect and is used mainly in oral care products.
Chemical PropertiesSlight menthol-like cooling effect aroma
UsesWS 3 is a selective transient receptor potential melastatin-8 ligand.
UsesPhysiological coolant in foods, beverages, toiletries, cosmetics and pharmaceuticals.
DefinitionChEBI: Ethyl menthane carboxamide is a p-menthane monoterpenoid.
Aroma threshold valuesAroma characteristics at 1.0%. Virtually odorless
Taste threshold valuesTaste characteristics at 10 to 100 ppm. Intense lingering cooling. The cooling sensation builds slow but steadily and grows to a lingering cooling mouthfeel with a slightly camphoraceous and minty character.
Flammability and ExplosibilityNotclassified
Trade nameWinsense WS-3 (Renessenz)
Biological ActivityCooling agent that is an agonist at TRPM8 receptors (EC 50 = 3.7 μ M).
Synthesis0.89 g (0.0091 mol) of polyphosphoric acid (85%) and 0.42 g (0.0091 mol) of ethanol were weighed. 0.54 g (0.0046 mol) of diethylcarbonate was added dropwise slowly while cooling in an ice bath, wherein the temperature increases slightly. After about 5 minutes, 0.5 g (0.0030 mol) of p-menthane-3-carbonitrile was added. The reaction solution was heated and stirred for 102 hours at 150??C. At the end of the reaction by GC, about 70% of desired N-Ethyl-p-menthane-3-carboxamide was formed.Synthesis_39711-79-0Fig The synthetic method 1 of N-Ethyl-p-menthane-3-carboxamide
N-Ethyl-p-menthane-3-carboxamide Preparation Products And Raw materials
Methylparaben N-Ethyl-p-menthane-3-carboxamide Methyl Acetonitrile N,N-Dimethylformamide Acetamide Acrylamide Basic Violet 1 Ethyl cellulose Isopropyl acetate Diethyl ether Ethyl acetate Polyacrylamide Methanol Polyamide Methyl acrylate Isopropyl alcohol Formamide

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