3,5,3′-Triiodo-L-thyronine

3,5,3'-Triiodo-L-thyronine is a naturally occurring iodinated thyronine amino acid derivative featuring a diphenyl ether (thyronine) core with three iodine substituents and an L-configured amino acid side chain bearing a free amino group and a carboxyl group. The molecule contains phenolic oxygen atoms on the aromatic rings that can participate in hydrogen bonding and acid-base behavior, while the multiple iodine substituents increase aromatic halogenation density and provide a distinct mass and spectroscopic signature for analytical work. In research settings, it is used as a defined iodinated amino acid building block or reference compound for studies of thyroid hormone analog structure-activity relationships, isotopic/iodine labeling strategies, and analytical method development involving iodinated aromatic amino acid derivatives.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP19401

CAS No:6893-02-3

Synonyms/Alias:liothyronine;triiodothyronine;3,3',5-Triiodo-L-thyronine;Liothyronin;Tresitope;3,5,3'-triiodothyronine;6893-02-3;L-Liothyronine;triothyrone;Liothyroninum;Liotironina;Triiodo-L-thyronine;T3;3,5,3'-Triiodo-L-thyronine;L-T3;O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine;Lyothyronine;3,3',5-Triiodothyronine;L-3,3',5-TriioDOThyronine;T3(aminoacid);T3(Hormone);Triiodothyronine,l-;L-3,5,3'-Triiodothyronine;(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoicacid;Cyronine

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M.F/Formula
C15H12I3NO4
M.W/Mr.
650.97

3,5,3'-Triiodo-L-thyronine is an iodinated thyroid hormone amino-acid derivative (L-thyronine scaffold) bearing three iodine atoms, commonly used as a chemically defined reference material in endocrine and thyroid-related chemical biology workflows. Its halogenated aromatic structure makes it a robust target for analytical quantification and isotope-dilution strategies, while its defined stereochemistry supports reproducible assay calibration and method validation. In research settings, 3,5,3'-Triiodo-L-thyronine is handled as a small-molecule standard rather than as a peptide-building amino acid.

1. Thyroid Hormone Quantification

3,5,3'-Triiodo-L-thyronine is widely used by analytical chemists and biochemistry laboratories to calibrate and validate LC-MS/MS and immunoassay workflows that quantify thyroid hormone species in complex matrices. Researchers rely on the defined tri-iodinated structure to generate accurate standard curves, assess extraction and recovery performance, and monitor run-to-run consistency during method development. Because the compound is a direct chemical target rather than a protein hydrolysate component, it is routinely selected for analytical specificity checks, instrument tuning, and reference material preparation in endocrine research and analytical method optimization.

2. Stable Isotope Dilution Standards

3,5,3'-Triiodo-L-thyronine is frequently employed in isotope-dilution LC-MS workflows when paired with appropriately labeled internal standards to improve quantitative accuracy for tri-iodinated thyroid hormone measurements. Metabolic and endocrine research groups use it as an external calibrant and/or matrix-matched reference to support relative quantification across time-course experiments, extraction conditions, and instrument batches. The tri-iodinated aromatic framework provides a strong mass signature for chromatographic and mass spectrometric discrimination, which is particularly valuable for resolving closely related iodothyronine species during quantitative studies.

3. Chemical Biology Probe Development

3,5,3'-Triiodo-L-thyronine is used in chemical biology and target-engagement research as a defined ligand scaffold for developing binding and competition assays involving thyroid hormone receptors and related binding proteins. Researchers incorporate this reference material into experimental designs that evaluate assay performance, establish concentration-response behavior, and verify specificity of detection reagents. In these workflows, the compound's well-defined identity and iodination pattern help ensure reproducible assay calibration when downstream readouts depend on accurate ligand dosing and consistent chemical composition.

Abbr
3,5,3′-Triiodo-L-thyronine
InChI
1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1
InChI Key
AUYYCJSJGJYCDS-LBPRGKRZSA-N
Canonical SMILES
C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CC(C(=O)O)N)I)I)O

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