An active metabolite of the thyroid hormones T3 and reverse T3
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3,3'-Diiodo-L-thyronine

Item No. 16748

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-(4-hydroxy-3-iodophenyl)-3-iodo-L-tyrosine
CAS Number
4604-41-5
Synonyms
  • L-3,3'-Diiodothyronine
  • 3,3'-T2
Molecular Formula
C15H13I2NO4
Formula Weight
525.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:30): 0.03 mg/ml
λmax
291 nm
SMILES
OC([C@@H](N)CC1=CC(I)=C(OC2=CC(I)=C(O)C=C2)C=C1)=O
InChi Code
InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)/t12-/m0/s1
InChi Key
CPCJBZABTUOGNM-LBPRGKRZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    3,3’-Diiodo-L-thyronine (3,3’-T2) is an active metabolite of the thyroid hormones 3,3’,5-triiodo-L-thryonine (T3; Item No. 30996) and 3,3’,5’-triiodo-L-thryonine (reverse T3; Item No. 17598).1 It is formed from T3 or reverse T3 via deiodination by peripheral deiodinases. 3,3’-T2 increases cytochrome c oxidase activity in osmotically treated mitochondria from the livers of hypothyroid and euthyroid rats and increases cytochrome c oxidase activity in liver homogenates from hypothyroid rats at 1 µM.2,3 It increases the resting metabolic rate by 27% and cytochrome c oxidase activity in the heart, liver, muscles, and brown adipose tissue (BAT) in a rat model of hypothyroidism.4 3,3’-T2 (250 µg/kg, i.p.) increases autophagy and reduces hepatic lipid accumulation in rats fed a high-fat diet.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. van der Spek, A.H., Fliers, E., and Boelen, A. The classic pathways of thyroid hormone metabolism. Mol. Cell. Endocrinol. 458, 29-38 (2017).

    2. Lanni, A., Moreno, M., Horst, C., et al. Specific binding sites for 3,3'-diiodo-L-thyronine (3,3'-T2) in rat liver mitochondria. FEBS Lett. 351(2), 237-240 (1994).

    3. Lanni, A., Moreno, M., Lombardi, A., et al. Rapid stimulation in vitro of rat liver cytochrome oxidase activity by 3,5-diiodo-ʟ-thyronine and by 3,3'-diiodo-ʟ-thyronine. Mol. Cell. Endocrinol. 99(1), 89-94 (1994).

    4. Moreno, M., Lanni, A., Lombardi, A., et al. How the thyroid controls metabolism in the rat: Different roles for triiodothyronine and diiodothyronines. J. Physiol. 505(Pt 2), 529-538 (1997).

    5. Iannucci, L.F., Cioffi, F., Senese, R., et al. Metabolomic analysis shows differential hepatic effects of T2 and T3 in rats after short-term feeding with high fat diet. Sci. Rep. 7(2023), (2017).