| Identification | Back Directory | [Name]
3,5-Diiodo-DL-tyrosine | [CAS]
66-02-4 | [Synonyms]
DIT
Itir
C01060
cemiod
flaianina
jodgorgon
apothyrin
NSC 97936
NSC 208959
Diidotyrosine
L-Tyr(3',5'-I2)
Iodogorgonic Acid
3,5-diiodo-tyrosin
Diiodogorgoic Acid
Diiodogorgonic Acid
H-DL-Tyr(3,5-I2)-OH
DL-3,5-Diiodotyrosine
Tyrosine, 3,5-diiodo-
3,5-Diiodo-DL-tyrosine
3,5-Diiodo-DL-tyrosine USP/EP/BP
rac-(R*)-2-(3,5-Diiodo-4-hydroxybenzyl)glycine
2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid
2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propanoic acid 95+%
rac-(R*)-2-Amino-3-(4-hydroxy-3,5-diiodophenyl)propionic acid
LRP1B (low-density Lipoprotein Receptor-related Protein 1B, LRP-1B, LRP | [EINECS(EC#)]
200-620-3 | [Molecular Formula]
C9H9I2NO3 | [MDL Number]
MFCD00063076 | [MOL File]
66-02-4.mol | [Molecular Weight]
432.98 |
| Chemical Properties | Back Directory | [Melting point ]
213°C (rough estimate) | [Boiling point ]
410.5±45.0 °C(Predicted) | [density ]
2.1461 (estimate) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
2.17±0.30(Predicted) | [color ]
Pale Beige to Light Beige | [Optical Rotation]
+2.920 (1 mol dm-3 HCl) | [Water Solubility ]
339.9mg/L(25 ºC) |
| Hazard Information | Back Directory | [Chemical Properties]
DL-3,5-diiodotyrosine occurs as flaky crystals. It decomposes at approximately 200°C. Its solubility in water is 0.149 g/L at 0°C, 0.340 g/L at 25°C, and 0.773 g/L at 50°C. It is soluble in dilute alkali. Boiling and cooling water and alcohol solutions does not produce a gel-like precipitate. However, L-3,5-diiodotyrosine crystals swell upon boiling in dilute alcohol solutions, and further boiling forms a colloidal precipitate. | [Uses]
3,5-Diiodo-DL-tyrosine is used for diagnosis of hypothyroidism caused by DEHAL1 gene defects. | [Synthesis]
General procedure for the synthesis of 2-amino-3-(4-hydroxy-3,5-diiodophenyl)propionic acid from D-tyrosine: D-tyrosine (2.00 g, 11.0 mmol) was dissolved in a mixed solution of ice acetic acid (14 mL) and concentrated hydrochloric acid (8 mL). Subsequently, iodine (2.8 g, 11.0 mmol) was added to this solution. A 30% hydrogen peroxide solution was slowly added dropwise to the reaction system at 65 °C. The temperature was maintained and the reaction mixture was stirred continuously for 30 minutes. Upon completion of the reaction, the solution was cooled to 15 °C and diluted with distilled water (100 mL). The pH of the mixture was adjusted to 5 with ammonia to promote precipitation of the target product. The precipitate was collected by filtration and washed with distilled water to give the final brown solid product 2-amino-3-(4-hydroxy-3,5-diiodophenyl)propionic acid in 80% yield. The melting point of the product was >250°C; 1H-NMR (300 MHz, DMSO-D2O) data were as follows: δ 7.46 (s, 2H, Ar-H), 4.10 (t, 1H, -CH-), 2.93 (m, 2H, -CH2-). | [References]
[1] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1325 - 1344
[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1907, vol. 51, p. 66
[3] Journal of the American Chemical Society, 1943, vol. 65, p. 1430
[4] Journal of the Chemical Society, 1949, p. Spl. 185, 188
[5] Chemische Berichte, 1935, vol. 68, p. 1108,1115 |
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