3,5-Diiodo-L-tyrosine dihydrate Chemical Properties

Melting point:

200 °C (dec.)(lit.)

alpha 

-20.7 º (c=2.5, 0.1N NaOH/H2O)

Boiling point:

546.5°C (rough estimate)

Density 

2.405±0.06 g/cm3(Predicted)

refractive index 

1.2 ° (C=5, 1mol/L HCl)

storage temp. 

2-8°C

solubility 

Aqueous Acid (Slightly), DMSO (Slightly)

pka

2.12(at 25℃)

form 

crystalline

color 

white

Water Solubility 

slightly soluble

Sensitive 

Light Sensitive

CAS DataBase Reference

300-39-0(CAS DataBase Reference)

NIST Chemistry Reference

3,5-Diiodo-l-tyrosine(300-39-0)

EPA Substance Registry System

L-Tyrosine, 3,5-diiodo- (300-39-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36/37-24/25

RIDADR 

2811

WGK Germany 

3

F 

8

TSCA 

Yes

HS Code 

29225090

MSDS

• Language:English Provider:3,5-Diiodo-L-tyrosine dihydrate
• Language:English Provider:SigmaAldrich

3,5-Diiodo-L-tyrosine dihydrate Usage And Synthesis

Description

Diiodotyrosine does not possess pronounced hormonal activity. However, it stops production of thyrotropic hormone by the anterior lobe of the hypophysis, which activates thyroid gland activity.

Chemical Properties

white to beige powder

Uses

It is used for hyperthyroid forms of endemic and sporadic goiters, diffuse, toxic goiters, and other illnesses accompanied by thyrotoxicity.

Uses

3,5-Diiodo-L-tyrosine is a reactant used in the synthesis of fluorescent unnatural amino acids bearing stilbene or vinylene backbones. Also used in the discovery of potent heterodimeric antagonists of inhibitor of Apoptosis proteins with prolonged anti-tumor activity.

Uses

3,5-Diiodo-L-tyrosine Dihydrate is a thyroid hormone receptor agonist.

Definition

ChEBI: A diiodotyrosine that is L-tyrosine carrying iodo-substituents at positions C-3 and C-5 of the benzyl group. It is an intermediate in the thyroid hormone synthesis.

Synthesis

Diiodotyrosine, 3,5-diiodotyrosine (25.2.1), is synthesized by directly iodinating tyrosine with iodine in the presence of sodium iodide in aqueous ethylamine, or in a mixture of acetic and hydrochloric acids with the addition of hydrogen peroxide.

Purification Methods

It forms crystals from H2O [solubility (g/L): 0.204 at 0o, 1.86 at 50o, 5.6 at 75o and 17.0 at 100o]. Also recrystallise it from 50% or 70% EtOH. When boiled in EtOH the crystals swell, and on further boiling a gelatinous precipitate is formed [Harrington Biochem J 22 1434 1928, Jurd J Am Chem Soc 77 5747 1955]. It also crystallises from cold dilute ammonia on adding acetic acid to pH 6. [Beilstein 14 IV 2370.]

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