3-IODO-L-TYROSINE Chemical Properties

Melting point:

210 °C (dec.)(lit.)

Density 

1.7280 (estimate)

storage temp. 

-20°C

solubility 

dilute aqueous acid: soluble

form 

Solid

Boiling point:

391.0±42.0 °C(Predicted)

pka

2.21±0.20(Predicted)

color 

White to off-white

Sensitive 

Light Sensitive

Merck 

14,5047

BRN 

2941266

Stability:

Hygroscopic

InChIKey

UQTZMGFTRHFAAM-ZETCQYMHSA-N

CAS DataBase Reference

70-78-0(CAS DataBase Reference)

EPA Substance Registry System

L-Tyrosine, 3-iodo- (70-78-0)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

8-10-23

HS Code 

29225090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-IODO-L-TYROSINE Usage And Synthesis

Chemical Properties

White Solid

Uses

A novel flavoprotein responsible for iodide salvage in thyroid glands. A tyrosine hydroxylase inhibitor.

Uses

3-iodo-l-tyrosine is used in the inhibition of tyrosine hydroxylase. 3-iodo-L-tyrosine is used in the rapid induction of prolactin secretion.

Uses

3-Iodo-L-tyrosine has been used as an inhibitor for tyrosine hydroxylase enzyme in Drosophila and silkworm pupae.

Definition

ChEBI: The monoiodotyrosine that is L-tyrosine carrying an iodo-substituent at position C-3 of the benzyl group.

General Description

Iodotyrosine coupled with di-iodotyrosine results in the synthesis of 3,5,3′-tri-iodothyronine (T3) or 3,3′,5′-tri-iodothyronine (rT3).

Biochem/physiol Actions

3-iodotyrosine (3-IY) inhibits tyrosine hydroxylase that catalyzes levodopa (L-DOPA) formation from tyrosine. Iodotyrosine deiodinase enzyme deficiency leads to elevated levels of 3-IY in serum and urine in severe hypothyroidism and goiter.

Purification Methods

Likely impurities are tyrosine, diiodotyrosine and iodide. Crystallise it by dissolving it in concentrated ammonia (~200mg in ~20mL), evaporate to ~5mL and NH4Cl is added to pH4.5—5.0. After a few hours at 0o, the amino acid crystallises in needles. It is filtered off, washed with a little ice-cold H2O and dried in a vacuum. Alternatively dissolve it in dilute ammonia at room temperature, then add dilute acetic acid to pH 6. Store it at 0o. Recrystallisation of ~250mg from H2O (~5mL) removes any diiodotyrosine. It is an inhibitor of tyrosine hydroxylase with a Ki of ~500nM. [Harrington & Rivers Biochem J 38 320 1944, Rivers Chem & Ind (London) 21 1956, Beilstein 14 III 1562, 14 IV 1562.]

3-IODO-L-TYROSINE(70-78-0)Related Product Information

• REVERSE T3
• 3,5-Diiodo-L-thyronine
• 3,3',5-Triiodo-L-thyronine
• 3,3',5-TRIIODOTHYROPROPIONIC ACID
• Thyroxine-4-hydroxy-3,5-diiodophenyl Ether DISCONTINUED
• 3,5-DIIODO-4'-(4-HYDROXYPHENOXY)BENZOIC ACID
• N-ForMyl Thyroxine
• 3,5,3',5'-Tetraiodo Thyroaldehyde
• 3,3',5,5'-TETRAIODOTHYRO-ACETIC ACID
• 4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzeneacetaMide
• 3,5,3',5'-Tetraiodo Thyrolactic Acid
• 3,3',5-TRIIODOTHYROACETIC ACID
• O-(4-hydroxy-3-iodophenyl)-3-iodo-L-tyrosine
• Liothyronine IMpurity E
• Levothyroxine impurity E
• Sodium levothyroxine
• Levothyroxine sodium
• N-Acetyl-3,5-diiodo-L-tyrosine