T3787

3,3′,5,5′-Tetraiodothyroacetic acid

≥98% (TLC), powder, thyrointegrin receptor antagonist

• Synonym(s): 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzeneacetic acid, Tetrac
• Linear Formula: C₁₄H₈O₄I₄
• CAS Number: 67-30-1
• Molecular Weight: 747.83
• EC Number: 200-649-1
• MDL number: MFCD00055932
• UNSPSC Code: 12352106
• PubChem Substance ID: 24900169
• NACRES: NA.77

Properties

• Product Name: 3,3′,5,5′-Tetraiodothyroacetic acid,
• solubility: acetone: soluble 19.60-20.40 mg/mL, clear, colorless (or faintly yellow to yellow)
• Quality Level: 200
• storage temp.: −20°C
• SMILES string: OC(=O)Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1
• InChI: 1S/C14H8I4O4/c15-8-4-7(5-9(16)13(8)21)22-14-10(17)1-6(2-11(14)18)3-12(19)20/h1-2,4-5,21H,3H2,(H,19,20)
• InChI key: PPJYSSNKSXAVDB-UHFFFAOYSA-N

Description

Application

3,3′,5,5′-Tetraiodothyroacetic acid has been used:

• as a positive control to study the effects of ioxynil (IOX)
• diethylstilbestrol (DES) exposure on zebrafish embryos[1]
• to study its effects on long-term potentiation (LTP) and long-term depression (LTD) in the dentate gyrus in urethane-anesthetized male rats[2]
• to determine its influence on the actions of thyroid-stimulating hormone
• thyroid-stimulating immunoglobulins in orbital fibroblast[3]

Biochem/physiol Actions

3,3′,5,5′-Tetraiodothyroacetic acid (Tetrac) is a deaminated analog of L-thyroxine (T4). It prevents the pro-angiogenesis actions of T4 and 3,5,3′-triiodo-L-thyronine.[4] It is a thyrointegrin receptor antagonist.[5] Tetrac prevents the binding of thyroid hormones.[6]

Studies in rats have reported that Tetrac may regulate TSH secretion under in vivo conditions¹.

Preparation Note

3,3′,5,5′-Tetraiodothyroacetic acid is soluble in acetone at 19.60 - 20.40 mg/ml and yields a clear, faint yellow to yellow solution.

Other Notes

Thyroid hormone analog

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H300
• Precautionary Statements: P264 - P301 + P310
• Hazard Classifications: Acute Tox. 2 Oral
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves