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HomeProduct name list3-IODO-L-TYROSINE

3-IODO-L-TYROSINE

Synonym(s):3-Monoiodo-L-tyrosine

  • CAS NO.:70-78-0
  • Empirical Formula: C9H10INO3
  • Molecular Weight: 307.09
  • MDL number: MFCD00002608
  • EINECS: 200-744-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-20 11:41:24
3-IODO-L-TYROSINE Structural

What is 3-IODO-L-TYROSINE?

Chemical properties

White Solid

The Uses of 3-IODO-L-TYROSINE

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.

The Uses of 3-IODO-L-TYROSINE

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

The Uses of 3-IODO-L-TYROSINE

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

What are the applications of Application

3-Iodo-L-tyrosine is a Tyrosine hydroxylase inhibitor.

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.]

Properties of 3-IODO-L-TYROSINE

Melting point: 210 °C (dec.)(lit.)
Density  1.7280 (estimate)
storage temp.  -20°C
solubility  dilute aqueous acid: soluble
Boiling point: 391.0±42.0 °C(Predicted)
pka 2.21±0.20(Predicted)
form  Solid
color  White to off-white
Sensitive  Light Sensitive
Merck  14,5047
BRN  2941266
Stability: Hygroscopic
CAS DataBase Reference 70-78-0(CAS DataBase Reference)
EPA Substance Registry System L-Tyrosine, 3-iodo- (70-78-0)

Safety information for 3-IODO-L-TYROSINE

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P310:Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 3-IODO-L-TYROSINE

InChIKey UQTZMGFTRHFAAM-ZETCQYMHSA-N

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