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O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine

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O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine Basic information
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine Chemical Properties
  • Melting point:234-238 °C(lit.)
  • alpha 23 º (c=2 in ethanol)
  • Boiling point:232°C (rough estimate)
  • Density 2.2155 (estimate)
  • Flash point:9°C
  • storage temp. −20°C
  • pkapKa 8.5 (Uncertain);8.4 (Uncertain);8.45 (Uncertain)
  • form powder
  • color Off-white to pale yellow
  • optical activity[α]25/D +23.0°, c = 2 in 1 N HCl: ethanol, 1:2
  • Water Solubility Insoluble in water, ethanol and propylene glycol. Soluble in dilute alkalies.
  • Sensitive Light Sensitive
  • Merck 14,5510
  • BRN 2710227
  • CAS DataBase Reference6893-02-3(CAS DataBase Reference)
Safety Information
MSDS
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine Usage And Synthesis
  • Chemical PropertiesOff-White Solid
  • UsesThyroidic drug;Thyroid hormone
  • UsesOne of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.
  • DefinitionChEBI: An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxi e in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.
  • brand nameTriomet-131 (Abbott); Tri-Thyrotope (Bristol-Myers Squibb).
  • Purification MethodsLikely impurities are as in thyroxine. Purify it by dissolving in dilute NH3 at ~20o, then crystallise it by addition of dilute acetic acid to pH 6. Alternatively 35g are purified by dissolving it in a mixture of EtOH (250mL) and 2N NaOH (100mL), then hot 2N HCl is added to the boiling solution until the pH is 4-5. After cooling for a few hours, the solid is filtered off and dried in a vacuum [m 233-235o(dec)]. [Chambers et al. J Chem Soc 2433 1949, Beilstein 14 III 1566, 14 IV 2373.]
O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine(6893-02-3)Related Product Information
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