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Basic Information
CAS No.: 51-48-9
Name: L-Thyroxine
Article Data: 27
Molecular Structure:
Molecular Structure of 51-48-9 (L-Thyroxine)
Formula: C15H11I4NO4
Molecular Weight: 776.875
Synonyms: Thyroxine,L- (8CI);(-)-Thyroxine;3,3',5,5'-Tetraiodo-L-thyronine;Henning;L-T4;L-Thyroxin;Levothyroxine;NSC 36397;T4;T4 (hormone);THX;Tetraiodothyronine;Thyrax;Thyreoideum;Thyroxin;Thyroxinal;Thyroxine;
EINECS: 200-101-1
Density: 2.635 g/cm3
Melting Point: 235 °C
Boiling Point: 576.306 °C at 760 mmHg
Flash Point: 302.339 °C
Solubility: insoluble in water
Appearance: Crystalline Solid
Hazard Symbols: HarmfulXn
Risk Codes: 40
Safety: 22-24/25-36
PSA: 92.78000
LogP: 5.25760
Synthetic route
51-48-9

L-thyroxine

Conditions
ConditionsYield
With sodium hypochlorite; tert-butylamine; sodium iodide In methanol at 20 - 30℃; Reagent/catalyst; Solvent;100%
With iodine; methylamine; potassium iodide In water at 0 - 5℃; for 2h;95%
With iodine; potassium iodide; sodium hydroxide In water at -10 - 10℃; Reagent/catalyst; Temperature;76.7%
With water; iodine; ethylamine; potassium iodide
With ammonia; iodine; potassium iodide

L-thyroxine, sodium salt hexahydrate

51-48-9

L-thyroxine

Conditions
ConditionsYield
With hydrogenchloride In methanol; dimethyl sulfoxide96%
300-39-0

3,5-diiodo-l-tyrosine

5,7-diiodo-1-oxaspiro[2.5]octa-4,7-dien-6-one

51-48-9

L-thyroxine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 24℃; for 16h; 0.2 M borate buffer, pH 8.0 (add. of 0.1 M NaOH);94%
70-40-6

3,3′-diiodothyronine

51-48-9

L-thyroxine

Conditions
ConditionsYield
Stage #1: 3,3′-diiodothyronine With methylamine In methanol at 25 - 30℃;
Stage #2: With iodine In methanol at -8 - 0℃;
Stage #3: With potassium dihydrogenphosphate; sodium hydrogensulfite In methanol at 15 - 20℃;
91.2%
300-39-0

3,5-diiodo-l-tyrosine

51-48-9

L-thyroxine

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; butan-1-ol
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 1 h
1.2: 2 h / 20 - 40 °C
2.1: diisopropylamine / water; butan-1-ol / 2 h / 20 - 90 °C
2.2: 2 h / 20 - 30 °C
3.1: acetic acid; hydrogen iodide / 5 h / 100 °C
4.1: methylamine / methanol / 25 - 30 °C
4.2: -8 - 0 °C
4.3: 15 - 20 °C
View Scheme
1027-28-7

N-acetyl-3,5-diiodo-L-tyrosine

51-48-9

L-thyroxine

Conditions
ConditionsYield
With air; water at 37℃; Erhitzen des Reaktionsprodukts mit wss. Salzsaeure und Essigsaeure;
300-39-0

3,5-diiodo-l-tyrosine

((7R,8S)-8-Hydroxy-5,7-diiodo-6-oxo-1-oxa-spiro[2.5]oct-4-en-2-yl)-oxo-acetic acid

51-48-9

L-thyroxine

Conditions
ConditionsYield
at 0℃; for 0.75h; Yield given;
27059-94-5

iodoacetamide

3,5-diiodo-thyronine

3,5-diiodo-thyronine

51-48-9

L-thyroxine

Conditions
ConditionsYield
With methanol; triethylamine
623-11-0

1-methyl-4-nitrosobenzene

300-39-0

3,5-diiodo-l-tyrosine

7722-84-1

dihydrogen peroxide

71-36-3

butan-1-ol

51-48-9

L-thyroxine

casein

casein

51-48-9

L-thyroxine

Conditions
ConditionsYield
Jodierung und anschliessende Hydrolyse;
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Specification

The Levothyroxine, with the CAS registry number 51-48-9, is also known as L-thyroxine. It belongs to the product categories of Amino Acids; Organics; Heterocyclic Compounds; Amino Acids & Derivatives; Intermediates & Fine Chemicals; Pharmaceuticals; Isotope Labeled Compounds. Its EINECS registry number is 200-101-1. This chemical's molecular formula is C15H11I4NO4 and molecular weight is 776.87002. Its IUPAC name is called (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid. This chemical's classification codes are Hormone; Human Data; Mutation data; Reproductive Effect. 

Physical properties of Levothyroxine: (1)ACD/LogP: 4.72; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.206; (4)ACD/LogD (pH 7.4): 1.678; (5)ACD/BCF (pH 5.5): 6.982; (6)ACD/BCF (pH 7.4): 2.069; (7)ACD/KOC (pH 5.5): 27.027; (8)ACD/KOC (pH 7.4): 8.01; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.795; (13)Molar Refractivity: 125.446 cm3; (14)Molar Volume: 294.745 cm3; (15)Surface Tension: 79.617 dyne/cm; (16)Density: 2.636 g/cm3; (17)Flash Point: 302.339 °C; (18)Enthalpy of Vaporization: 90.781 kJ/mol; (19)Boiling Point: 576.306 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be extracted from animal thyroid, but also can use 5-bis iodine-L-tyrosine as raw material.

Levothyroxine can be used as a hormone replacement for patients with thyroid problems. This medicine is a hormone replacement usually given to patients with hypothyroidism. Levothyroxine is also frequently used to treat goiter because it usually lowers the levels of thyroid-stimulating hormone, a hormone that is considered goitrogenic. This chemical can be used in veterinary. The dosage for dogs with hypothyroidism is usually a twice daily dose of between 10-40 μg per kg of body weight.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. There is limited evidence of a carcinogenic effect. You should not breathe its dust. What's more, you must avoid contacting it with skin and eyes. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)CC(C(=O)O)N
(2)Isomeric SMILES: C1=C(C=C(C(=C1I)OC2=CC(=C(C(=C2)I)O)I)I)C[C@@H](C(=O)O)N
(3)InChI: InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1
(4)InChIKey: XUIIKFGFIJCVMT-LBPRGKRZSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 328ug/kg (0.328mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Pediatrics. Vol. 73, Pg. 313, 1984.
man TDLo oral 63ug/kg (0.063mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 517, 1983.
man TDLo oral 10286ug/kg (10.286mg/kg) BEHAVIORAL: EXCITEMENT

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

GASTROINTESTINAL: NAUSEA OR VOMITING
Veterinary and Human Toxicology. Vol. 41, Pg. 323, 1999.
women TDLo oral 400ug/kg/2D-I (0.4mg/kg) BEHAVIORAL: COMA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Intensive Care Medicine. Vol. 13, Pg. 33, 1987.