| Identification | More | [Name]
3-IODO-L-TYROSINE | [CAS]
70-78-0 | [Synonyms]
3-IODO-L-TYROSINE
3-IODO-TYROSINE
3-MONOIODO-L-TYROSINE
H-3-IODO-TYR-OH
H-3-I-PHE(4-OH)-OH
H-3-I-TYR-OH
H-L-TYR(3-I)-OH
H-TYR(3-I)-OH
H-TYR(M-I)-OH
L-TYROSINE, 3-IODO-
M-IODO-L-TYROSINE
S(-)-3-IODO-4-HYDROXY-PHENYLAMINE
3-Monoiodo-L-tyrosine 3-Iodo-L-tyrosine
Iodotyrosine
(2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoic acid
3-IODO-L-TYROSINE 97% | [EINECS(EC#)]
200-744-8 | [Molecular Formula]
C9H10INO3 | [MDL Number]
MFCD00002608 | [Molecular Weight]
307.09 | [MOL File]
70-78-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
210 °C (dec.)(lit.)
| [density ]
1.7280 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
dilute aqueous acid: soluble
| [Boiling point ]
391.0±42.0 °C(Predicted) | [form ]
Solid | [pka]
2.21±0.20(Predicted) | [color ]
White to off-white | [Sensitive ]
Light Sensitive | [Usage]
A tyrosine hydroxylase inhibitor | [Merck ]
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) |
| Hazard Information | Back Directory | [Chemical Properties]
White Solid | [Uses]
A novel flavoprotein responsible for iodide salvage in thyroid glands. 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.] |
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