Buy N-Ethyl-p-menthane-3-carboxamide (BT-254242)

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N-Ethyl-p-menthane-3-carboxamide

Catalog Number: BT-254242

CAS Number: 39711-79-0

Molecular Formula: C13H25NO

Molecular Weight: 211.34 g/mol

The product is for non-human research only. Not for therapeutic or veterinary use.

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Product Introduction

Description

N-Ethyl-p-menthane-3-carboxamide, also known as menthol derivative WS-23, is a synthetic cooling agent that is widely used in various industries, including food, cosmetics, and pharmaceuticals. It is a white crystalline powder with a minty odor and taste. WS-23 is a popular alternative to menthol due to its stronger cooling effect, longer-lasting sensation, and lack of bitterness.

Properties

CAS Number

39711-79-0

Product Name

N-Ethyl-p-menthane-3-carboxamide

IUPAC Name

N-ethyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide

Molecular Formula

C13H25NO

Molecular Weight

211.34 g/mol

InChI

InChI=1S/C13H25NO/c1-5-14-13(15)12-8-10(4)6-7-11(12)9(2)3/h9-12H,5-8H2,1-4H3,(H,14,15)

InChI Key

VUNOFAIHSALQQH-UHFFFAOYSA-N

SMILES

CCNC(=O)C1CC(CCC1C(C)C)C

Solubility

Insoluble in water
Soluble (in ethanol)

Synonyms

N-Ethyl-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide

Canonical SMILES

CCNC(=O)C1CC(CCC1C(C)C)C

Method of Synthesis or Extraction

WS-23 can be synthesized by reacting N-Ethyl-p-menthane-3-carboxamide with ethyl chloroformate in the presence of a base, such as triethylamine. The reaction yields WS-23 and ethyl alcohol as byproducts. Another method involves reacting N-Ethyl-p-menthane-3-carboxamide with ethyl isocyanate in the presence of a catalyst, such as dibutyltin dilaurate. The reaction yields WS-23 and urethane as byproducts. Both methods have high efficiency and yield, with WS-23 purity of over 99%. However, the use of toxic and flammable reagents, as well as the generation of hazardous byproducts, poses environmental and safety considerations.

Chemical Structure and Biological Activity

WS-23 has a chemical formula of C18H27NO2 and a molecular weight of 293.42 g/mol. Its chemical structure consists of a menthane backbone with an ethyl carboxamide group at the 3-position. WS-23 acts as a TRPM8 agonist, which is a cold receptor protein found in sensory neurons. It binds to the receptor and triggers a calcium influx, leading to a cooling sensation. WS-23 has a higher potency and selectivity for TRPM8 than N-Ethyl-p-menthane-3-carboxamide, making it a more effective cooling agent.

Biological Effects

WS-23 has been shown to affect cell function and signal transduction in various studies. It can modulate ion channels, such as TRPM8 and TRPA1, which are involved in pain and inflammation. WS-23 can also activate brown adipose tissue, which is responsible for thermogenesis and energy expenditure. These biological effects suggest that WS-23 may have potential therapeutic applications, such as pain relief, weight loss, and metabolic disorders. However, WS-23 may also have toxic effects, such as cytotoxicity and genotoxicity, at high concentrations.

Applications

WS-23 has a wide range of applications in different fields. In medical research, WS-23 has been used as a tool compound to study TRPM8 and its role in pain and inflammation. WS-23 has also been investigated as a potential drug candidate for obesity and metabolic disorders. In clinical trials, WS-23 has been shown to reduce body weight and improve glucose metabolism in obese patients. However, the long-term safety and efficacy of WS-23 as a drug remain to be determined. In environmental research, WS-23 has been used to study the effects of cooling agents on ecosystems and pollution management. WS-23 has been found to have low toxicity and biodegradability, making it a sustainable and environmentally friendly option. In industrial research, WS-23 has been used to improve product quality and efficiency in various applications, such as food and cosmetics. WS-23 has also been used to enhance the cooling effect of air conditioning systems and refrigerants. However, the health and safety considerations of WS-23 in industrial settings need to be addressed.

Future Perspectives and Challenges

WS-23 has shown great potential in various applications, but there are still limitations and challenges that need to be addressed. The safety and toxicity of WS-23 at high concentrations need to be thoroughly investigated. The long-term effects of WS-23 on human health and the environment need to be monitored. The development of more efficient and sustainable methods of synthesis or extraction is also needed. The discovery of new biological targets and mechanisms of action of WS-23 may lead to new therapeutic applications. The optimization of WS-23 properties, such as taste and odor, may also expand its use in different industries.
Conclusion:
WS-23 is a synthetic cooling agent that has gained popularity due to its stronger and longer-lasting cooling effect compared to N-Ethyl-p-menthane-3-carboxamide. WS-23 has a menthane backbone with an ethyl carboxamide group at the 3-position and acts as a TRPM8 agonist. WS-23 has potential therapeutic applications in pain relief, weight loss, and metabolic disorders, as well as industrial applications in improving product quality and efficiency. However, the safety and toxicity of WS-23 at high concentrations, as well as its long-term effects on human health and the environment, need to be thoroughly investigated. The development of more efficient and sustainable methods of synthesis or extraction, as well as the optimization of WS-23 properties, may lead to new applications and benefits.

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