3,5-Diiodo-L-tyrosine ethyl ester hydrochloride is a halogenated tyrosine derivative in which the phenolic side chain of L-tyrosine bears iodine atoms at the 3 and 5 positions, and the carboxyl group is esterified as an ethyl ester while the compound is present as a hydrochloride salt. The molecule contains a phenolic hydroxyl group, an aromatic ring substituted with two iodine atoms that increase halogen density for radiolabeling or heavy-atom labeling contexts, and an amino functionality that is protonated under hydrochloride conditions, while the ethyl ester masks the carboxylate to modulate polarity and reactivity during synthesis. It is used as a chemically defined building block and substrate for preparing iodinated tyrosine-containing peptides and peptide-related intermediates, as well as for analytical method development and molecular labeling workflows where the diiodinated aromatic motif provides a convenient handle for downstream derivatization.
CAT No: CP02160
CAS No:74051-47-1
Synonyms/Alias:74051-47-1;L-3,5-Diiodotyrosineethylesterhydrochloride;3,5-Diiodo-L-tyrosineethylesterhydrochloride;Tyrosine,3,5-diiodo-,ethylester,hydrochloride,L-;AC1MHTQH;C11H13I2NO3.HCl;SCHEMBL2595594;CTK8G0460;H-Tyr(3,5-I2)-OEt.HCl;MolPort-003-909-554;5261AH;KM1588;AM82358;KB-28743;LS-158277;ethyl(2S)-2-amino-3-(4-hydroxy-3,5-diiodophenyl)propanoatehydrochloride
3,5-Diiodo-L-tyrosine ethyl ester hydrochloride is an iodinated tyrosine derivative featuring two iodine atoms on the phenolic ring, supplied as an ethyl ester hydrochloride salt. This halogenated aromatic side chain makes it a practical building block for radioiodination-adjacent chemistry and for generating tyrosine-containing intermediates where iodine substitution pattern is critical. The esterified carboxyl group supports downstream coupling chemistry in synthetic workflows that require a protected/activated tyrosine motif prior to final functional group conversion.
1. Iodinated Tyrosine Building Block
3,5-Diiodo-L-tyrosine ethyl ester hydrochloride is used as a defined iodinated tyrosine building block in the synthesis of iodinated aromatic amino-acid derivatives and tyrosine-containing intermediates for research and specialty chemical manufacturing. The 3,5-diiodo substitution pattern is a key structural element when preparing compounds that require an iodine-rich phenolic ring, such as analogs used to benchmark iodinated phenol reactivity or to standardize downstream analytical behavior. Researchers in medicinal chemistry and chemical development often select this specific iodinated, esterified form to control the substitution pattern while maintaining a carboxyl group in a coupling-ready ester state during intermediate assembly.
2. Peptide Intermediate For Iodinated Residues
3,5-Diiodo-L-tyrosine ethyl ester hydrochloride is commonly employed as an iodinated tyrosine residue precursor for constructing peptides and peptide-like structures that incorporate an iodine-substituted phenolic side chain. Peptide synthesis groups use the ethyl ester hydrochloride form as a practical intermediate when building iodinated tyrosine segments for subsequent conversion to the corresponding carboxylic acid or for coupling into protected peptide fragments, depending on the selected synthesis strategy. The presence of the phenolic iodines supports preparation of tyrosine analog peptides used in structure-activity relationship studies, analytical method development, and chemical biology experiments where the iodine pattern must be preserved through peptide assembly and downstream handling.
3. Radiolabeling-Compatible Aromatic Scaffold
3,5-Diiodo-L-tyrosine ethyl ester hydrochloride is used as a scaffold in workflows that require iodinated tyrosine motifs for radioiodination-related chemistry and for preparing iodinated standards that reflect the aromatic iodine substitution pattern. Laboratories working on tracer chemistry and analytical reference materials often value the defined 3,5-diiodo phenolic ring because it provides a consistent starting point for generating iodinated derivatives used in labeling and quantification contexts. Because the compound is supplied as a hydrochloride salt with the carboxyl group esterified, it is also handled as a discrete intermediate in multi-step labeling or derivatization sequences where controlled functional group presentation improves reproducibility.
4. Analytical Reference And Method Development
3,5-Diiodo-L-tyrosine ethyl ester hydrochloride is applied in analytical chemistry and instrumental method development as a structurally defined iodinated tyrosine derivative for calibrations, retention/response benchmarking, and confirmation of iodinated phenol-containing analytes. Mass spectrometry and chromatographic method developers may use this compound to evaluate how iodine substitution affects ionization and detection behavior for tyrosine-derived standards, especially when developing assays that must distinguish iodinated aromatic species. The fixed 3,5-diiodo substitution and ester hydrochloride form help ensure that reference materials match the target structural features during method optimization and routine analytical verification.
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