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L-Triiodothyronine
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Name

L-Triiodothyronine

 EINECS 229-999-3
CAS No. 6893-02-3 Density 2.387 g/cm3
PSA 92.78000 LogP 4.65300
Solubility Insoluble in water, ethanol and propylene glycol Melting Point 234-238 °C(lit.)
Formula C15H12I3NO4 Boiling Point 563.527 °C at 760 mmHg
Molecular Weight 650.978 Flash Point 294.611 °C
Transport Information N/A Appearance Off-white solid
Safety 26-36 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 6893-02-3 (O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Alanine,3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-, L- (8CI);Thyronine,3,3',5-triiodo-, L- (6CI);3,3',5-Triiodo-L-thyronine;3,3',5-Triiodothyronine;3,5,3'-Triiodothyronine;4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine;Cyronine;L-3,3',5-Triiodothyronine;L-Liothyronine;L-T3;Liothyronin;Liothyronine;NSC 80203;T3;T3 (Hormone);T3 (amino acid);Tresitope;Triiodo-L-thyronine;Triiodothyronine;

Article Data 13

L-Triiodothyronine Synthetic route

3,5-diiodo-l-tyrosine

3,5-diiodo-l-tyrosine

5-Iodo-1-oxa-spiro[2.5]octa-4,7-dien-6-one

6893-02-3

triiodothyronine

1041-01-6, 534-51-0, 5563-89-3, 299-82-1

3,5-diiodo-L-thyronine

6893-02-3

triiodothyronine

Conditions
ConditionsYield
With sodium hydroxide; iodine
With ammonia; iodine; potassium iodide
With iodine; ethylamine
With iodine; ethylamine; sodium iodide In water at 0 - 20℃; for 10h;
Multi-step reaction with 2 steps
1: sodium iodide; ethylamine; iodine / water / 7 h / 0 - 22 °C / Large scale
2: acetic acid / water / Large scale
View Scheme

4-Hydroxymethyl-2-iodo-cyclohexa-2,5-dienone

6893-02-3

triiodothyronine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 32 percent / NaBiO3 / ethyl acetate; acetic acid; H2O / 1.33 h
2: 70 percent / dimethylformamide / 16 h / 24 °C / 0.2 M borate buffer, pH 8.0 (add. of 0.1 M NaOH)
View Scheme
300-30-1

thyroxine

6893-02-3

triiodothyronine

55-06-1

liothyronine sodium

6893-02-3

triiodothyronine

Conditions
ConditionsYield
With acetic acid In water Large scale;
6893-02-3

triiodothyronine

O-[3-iodo-4-(sulfooxy)phenyl]-3,5-diiodo-L-tyrosine sodium salt

Conditions
ConditionsYield
Stage #1: triiodothyronine With chlorosulfonic acid In N,N-dimethyl acetamide at 5 - 10℃; Inert atmosphere; Large scale;
Stage #2: With sodium carbonate In N,N-dimethyl acetamide; water at 10 - 20℃; for 1h; Large scale;		68%
Stage #1: triiodothyronine With chlorosulfonic acid In N,N-dimethyl acetamide at -5 - 5℃; for 4.66667h; Inert atmosphere;
Stage #2: With sodium carbonate In N,N-dimethyl acetamide; water for 1.5h; Temperature; Inert atmosphere;		62%
6893-02-3

triiodothyronine

O-[3-iodo-4-(sulfooxy)phenyl]-3,5-diiodo-N-sulfo-L-tyrosine disodium salt

Conditions
ConditionsYield
Stage #1: triiodothyronine With chlorosulfonic acid In pyridine at 15 - 20℃; for 1.25h;
Stage #2: With sodium hydrogencarbonate In pyridine; water pH=8.2;		27%
6893-02-3

triiodothyronine

L-Triiodothyronine sulfate

Conditions
ConditionsYield
With chlorosulfonic acid; trifluoroacetic acid at 0℃; for 0.166667h;25%
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

6893-02-3

triiodothyronine

(R)-2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-3-[4-(4-hydroxy-3-iodo-phenoxy)-3,5-diiodo-phenyl]-propionic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol
3392-07-2

tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate

6893-02-3

triiodothyronine

Boc-Gly-T3

Conditions
ConditionsYield
Stage #1: tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate; triiodothyronine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 15h;
Stage #2: With water In tetrahydrofuran

L-Triiodothyronine Specification

The L-Triiodothyronine, with the CAS registry number 6893-02-3, is also known as L-3,3',5-Triiodothyronine. It belongs to the product categories of Amino Acids & Derivatives; Intermediates & Fine Chemicals; Labeling and Diagnostics Reagents; Pharmaceuticals. Its EINECS number is 229-999-3. This chemical's molecular formula is C15H12I3NO4 and molecular weight is 650.97. What's more, its systematic name is O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine. Its classification codes are: (1)Drug / Therapeutic Agent; (2)Reproductive Effect. This chemical is used as a fat loss supplement, and it is also used in the treatment of depressive disorders. It should be protected from light.

Physical properties of L-Triiodothyronine are: (1)ACD/LogP: 3.906; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.41; (4)ACD/LogD (pH 7.4): 1.32; (5)ACD/BCF (pH 5.5): 1.74; (6)ACD/BCF (pH 7.4): 1.43; (7)ACD/KOC (pH 5.5): 10.10; (8)ACD/KOC (pH 7.4): 8.31; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 92.78 Å2; (13)Index of Refraction: 1.763; (14)Molar Refractivity: 112.539 cm3; (15)Molar Volume: 272.672 cm3; (16)Polarizability: 44.614×10-24cm3; (17)Surface Tension: 75.9 dyne/cm; (18)Density: 2.387 g/cm3; (19)Flash Point: 294.611 °C; (20)Enthalpy of Vaporization: 89.103 kJ/mol; (21)Boiling Point: 563.527 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(cc1Oc2c(cc(cc2I)C[C@@H](C(=O)O)N)I)I)O
(2)Std. InChI: InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1
(3)Std. InChIKey: AUYYCJSJGJYCDS-LBPRGKRZSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LDLo oral 7500mg/kg (7500mg/kg)   Roczniki Panstwowego Zakladu Higieny. Vol. 32, Pg. 197, 1981.

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