A thyroid hormone variant
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3,3',5'-Triiodo-L-thyronine

Item No. 17598

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-(4-hydroxy-3,5-diiodophenyl)-3-iodo-L-tyrosine
CAS Number
5817-39-0
Synonyms
  • Reverse T3
  • rT3
  • 3,3’,5’-T3
Molecular Formula
C15H12I3NO4
Formula Weight
651.0
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/ml
λmax
211, 290 nm
SMILES
IC1=C(O)C(I)=CC(OC2=CC=C(C[C@H](N)C(O)=O)C=C2I)=C1
InChi Code
InChI=1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1
InChi Key
HZCBWYNLGPIQRK-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $109

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    10 mg

    $207

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    25 mg

    $464

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    50 mg

    $818

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    Product Description

    3,3',5’-Triiodo-L-thyronine, also known as reverse T3 (rT3), is a thyroid hormone generated by deiodination of the prohormone thyroxine. It is about 1,000-fold less active at the thyroid hormone receptors TRα and TRβ than 3,3',5-triiodo-L-thyronine (Item No. 16028) and commonly described as inactive.1,2 However, high serum levels of rT3 are found in neonates and in certain conditions.3,4,5,6 It reportedly activates TRΔα1, a native form of TRα that lacks a nuclear localization signal and functions in the cytoplasm.7 Through this action, rT3 initiates actin polymerization, particularly in astrocytes and neurons.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Collingwood, T.N., Sydenham, M., Page, M.J., et al. Functional properties of human thyroid hormone receptor β1 overexpressed using baculovirus. FEBS Lett. 291(2), 315-318 (1991).

    2. Koury, E.J., Pawlyk, A.C., Berrodin, T.J., et al. Characterization of ligands for thyroid receptor subtypes and their interactions with co-regulators. Steroids 74(2), 270-276 (2009).

    3. Tien, E.S., Matsui, K., Moore, R., et al. The nuclear receptor constitutively active/androstane receptor regulates type 1 deiodinase and thyroid hormone activity in the regenerating mouse liver. J. Pharmacol. Exp. Ther. 320(1), 307-313 (2007).

    4. Ohguchi, H., Tanaka, T., Uchida, A., et al. Hepatocyte nuclear factor 4α contributes to thyroid hormone homeostasis by cooperatively regulating the type 1 iodothyronine deiodinase gene with GATA4 and Krüppel-like transcription factor 9. Mol. Cell. Biol. 28(12), 3917-3931 (2008).

    5. Economidou, F., Douka, E., Tzanela, M., et al. Thyroid function during critical illness. Hormones 10(2), 117-124 (2011).

    6. Novitzky, D., and Cooper, D.K.C. Thyroid hormone and the stunned myocardium. J. Endocrinol. 223(1), R1-R8 (2014).

    7. Senese, R., Cioffi, F., de Lange, P., et al. Thyroid: Biological actions of “nonclassical” thyroid hormones. J. Endocrinol. 221(2), R1-R12 (2014).