3,5-Diiodo-DL-tyrosine Chemical Properties

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 activity

+2.920 (1 mol dm-3 HCl)

Water Solubility 

339.9mg/L(25 ºC)

Safety Information

HS Code 

29214980

MSDS

• Language:English Provider:3,5-Diiodo-DL-tyrosine

3,5-Diiodo-DL-tyrosine Usage And Synthesis

Chemical Properties

DL-3,5-Diiodotyrosine is a lamellar crystal. Decomposed at about 200℃. Solubility in water: 0.149g/L at 0°C, 0.340g/L at 25°C, 0.773g/L at 50°C. Soluble in dilute alkali. Boiled and cooled water and alcohol solution will not produce gel-like precipitate. In contrast, L-3,5-diiodotyrosine crystallizes and dissolves after boiling in dilute alcoholic solution, and a gel-like precipitate is formed by continued boiling.

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

3,5-Diiodo-DL-tyrosine(66-02-4)Related Product Information

• N-Acetyl-3,5-diiodo-L-tyrosine
• LevosiMendan iMpurity
• Levothyroxine Impurity 16
• 3,3',5-TRIIODOTHYROPROPIONIC ACID
• Levothyroxine Related Compound (2-Acetamido-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl) Propanoic Acid)
• Levothyroxine Impurity
• Levothyroxine Impurity 54
• Levosimendan Impurity 8
• Levothyroxine Impurity
• 3,5-DIIODOTHYROACETIC ACID
• 3-Iodo-DL-tyrosine
• Levothyroxine Related Compound (2-Acetamido-3-(4-acetoxy-3,5-diiodophenyl)propanoic Acid)
• Levothyroxine EP Impurity B
• Levothyroxine Impurity 16
• Levothyroxine Impurity 12
• (2S,2''S)-3,3''-(((6,6''-Dihydroxy-5-iodo-[1,1''-biphenyl]-3,3''-diyl)bis(oxy))bis(3,5-diiodo-4,1-phenylene))bis(2-aminopropanoic Acid)
• Levothyroxine Impurity
• (S)-2-(2-Amino-3-(4-(3,5-diiodo-4-methoxyphenoxy)-3,5-diiodophenyl)propanamido)acetic Acid