D-Tryptophan Methyl Ester Hydrochloride, with the CAS number 14907-27-8, is a chiral amino acid derivative, also known as H-D-Trp-OMe·HCl or (R)-Methyl 2-amino-3-indolylpropanoate hydrochloride. Its molecular formula is C₁₂H₁₅ClN₂O₂, molecular weight is 254.71 g/mol, and it is a key intermediate in pharmaceutical and organic synthesis, widely used in drug development and biochemical research.
Physically, it presents as a white to off-white crystalline powder with a melting point of 213-216℃ and a boiling point of 390.6℃ at 760mmHg. It is slightly soluble in water, methanol, and DMSO, with a specific rotation [α]²⁰/D of -19° (in methanol, c=5). Chemically, the hydrochloride salt form enhances its stability and solubility, while its esterified carboxyl group and free amino group make it a versatile chiral building block, compatible with various organic synthesis reactions but sensitive to strong oxidants.
Its core application lies in the pharmaceutical industry, where it serves as a pivotal intermediate for synthesizing certain PDE5 inhibitors used in treating erectile dysfunction. It is also widely applied in peptide synthesis, acting as a C-terminus protecting group for D-tryptophan to enable controlled peptide bond formation.
In biochemical research, it is used as a reagent for studying protein synthesis and the kynurenine pathway, while in the food industry, it functions as a flavor enhancer and preservative to improve product taste and shelf life. Additionally, it is utilized in organic synthesis for preparing fine chemicals and cosmetics.
Safety-wise, it is classified as an irritant (hazard code Xi) and slightly harmful to water. It should be stored at 2-8℃ in a sealed, cool, dry, and dark environment, away from oxidants. Proper protective equipment is recommended during handling. With its unique chiral properties and high reactivity, it is an indispensable raw material in pharmaceuticals, biochemistry, and fine chemicals.
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