Trans-4-aminocyclohexanecarboxylic acid hydrochloride, with the CAS number 27960-59-4, is a chiral cyclic amino acid hydrochloride derivative, also known as trans-4-Aminocyclohexanecarboxylic acid HCl or trans-ACH HCl. Its molecular formula is C₇H₁₄ClNO₂, and its molecular weight is 179.64 g/mol. It features a trans-configured cyclohexane ring with an amino group at the 4-position and a carboxyl group at the 1-position, combined with a hydrochloride salt form, offering high water solubility, good chemical stability, and specific reactivity, making it widely applied in pharmaceutical synthesis, peptide chemistry, and biochemistry research.
Physically, it appears as a white to off-white crystalline powder or granular solid. It has a melting point of approximately 280-285℃ (decomposition) and is highly soluble in water and polar organic solvents such as methanol and ethanol, while slightly soluble in dimethylformamide and insoluble in non-polar solvents. It is optically inactive due to its racemic nature and has low hygroscopicity, remaining stable under normal temperature and pressure when stored properly, facilitating easy handling, storage, and formulation in various chemical and biological processes.
Chemically, its core trans-cyclohexane scaffold, amino group, carboxyl group, and hydrochloride moiety are key to its properties. The trans configuration ensures structural rigidity, which is crucial for its role as a peptide mimic. The hydrochloride salt form enhances water solubility and chemical reactivity compared to the free acid form. It is stable under neutral and weakly acidic conditions but may undergo decomposition under strong alkali or high-temperature environments, and can participate in amidation, esterification, and substitution reactions, making it an ideal building block for organic synthesis.
Its core applications focus on pharmaceutical synthesis and peptide chemistry. As a key intermediate, it is widely used in the synthesis of peptide drugs, antiviral agents, and chiral pharmaceuticals, particularly compounds targeting neurological disorders and infectious diseases. Its cyclic structure is often used to constrain peptide backbones, improving the metabolic stability and biological activity of the resulting products. Additionally, it serves as a biochemical reagent for studying cyclic amino acid metabolism and enzyme activity in laboratory research.
Safety-wise, it is generally recognized as safe under normal handling, with mild irritation potential to the skin, eyes, and respiratory tract upon direct contact. It should be handled in a well-ventilated area with appropriate protective equipment. It should be stored in a sealed, cool, dry, and dark environment at 2-8℃, away from oxidants, moisture, and high temperatures to prevent decomposition and maintain purity. With its unique structural characteristics and versatile applications, it is an indispensable raw material in pharmaceutical and life science fields.
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