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
- Mol File:
- 39711-79-0.mol
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℃
- refractive index
- 1.4410 (estimate)
- FEMA
- 3455 | N-ETHYL-2-ISOPROPYL-5-METHYLCYCLOHEXANE CARBOXAMIDE
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- DMSO: ≥ 100 mg/mL (473.17 mM); Water: < 0.1 mg/mL (insoluble)
- pka
- 16.27±0.60(Predicted)
- form
- powder to crystal
- color
- White to Almost white
- Odor
- at 25.00 % in dipropylene glycol. mild mentholic minty
- Odor Type
- minty
- Water Solubility
- insoluble
- Merck
- 14,3825
- JECFA Number
- 1601
- InChIKey
- VUNOFAIHSALQQH-UHFFFAOYSA-N
- LogP
- 2.902 at 25℃
- CAS DataBase Reference
- 39711-79-0(CAS DataBase Reference)
- EPA Substance Registry System
- Cyclohexanecarboxamide, N-ethyl-5-methyl-2-(1-methylethyl)- (39711-79-0)
MSDS
- Language:English Provider:N-Ethyl-p-menthane-3-carboxamide
- Language:English Provider:ACROS
N-Ethyl-p-menthane-3-carboxamide Usage And Synthesis
Chemical Properties
white crystalline powder
Chemical Properties
N-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 Properties
Slight menthol-like cooling effect aroma
Uses
WS 3 is a selective transient receptor potential melastatin-8 ligand.
Uses
Physiological coolant in foods, beverages, toiletries, cosmetics and pharmaceuticals.
Definition
ChEBI: Ethyl menthane carboxamide is a p-menthane monoterpenoid.
Aroma threshold values
Aroma characteristics at 1.0%. Virtually odorless
Taste threshold values
Taste 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 Explosibility
Not classified
Trade name
Winsense WS-3 (Renessenz)
Biological Activity
Cooling agent that is an agonist at TRPM8 receptors (EC 50 = 3.7 μ M).
Synthesis
0.89
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.
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