Basic information
- CAS
51-49-0- Standard SMILES
[NH3+][C@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(=O)[O-]- InChIKey
XUIIKFGFIJCVMT-GFCCVEGCSA-N- Molecular formula
- C15H11I4NO4
- Average molar mass
- 776.87 g/mol
- Monoisotopic mass
- 776.6867
Overview
The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism.
Names & identifiers
- Preferred name
- (2R)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
- IUPAC
- (2R)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
- English name
- D-Thyroxine
- Molecular formula
- C15H11I4NO4
- Molecular weight
- 776.87
Names & synonyms
D-T4DEBETROLD-THYROXINEof D-ThyroxinedextrothyroxineD-Thyroxine,97%Thyroxine, D- (8CI)D-thyroxine free acidD-Thyroxine USP/EP/BPLevothyroxine D-Isomer
Database identifiers
- CAS
51-49-0- PubChem CID
- 90657408
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 97.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 414
Experimental & physicochemical properties
LogP4
Solubility8.98e-03 g/L
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
235-236 °C
235 - 236 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 235 °C · ~235 °C (dec.)
- alpha
- 21546 · 21546 +2.97° (0.74 g in 6 g of 0.5N NaOH and 14 g of alcohol)
- Boiling point
- 576.3 · 576.3±50.0 °C(Predicted)
- Density
- 2.444 · 2.4440 (estimate)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- solubility
- Acidic Alcohol (Slightly), Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 8-10
- wgk
- 3
- risk_code
- 20/21/22-40
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36/37-36-22
- Hazard statements
- H312-H302-H332
- Precautionary statements
- P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312-P264-P270-P301+P312-P330-P501
Chemistry & industry
Pharmacology
PharmacodynamicsDextrothyroxine, the dextrorotary isomer of the synthetic thyroxine, is a antihyperlipidemic.
Mechanism of Action
Dextrothyroxine is a antihyperlipidemic. The mechanism of action is not completely understood, but dextrothyroxine apparently acts in the liver to stimulate formation of low-density lipoprotein (LDL) and, to a much greater extent, to increase catabolism of LDL. This leads to increased excretion of cholesterol and bile acids via the biliary route into the feces, with a resulting reduction in serum cholesterol and LDL. Dextrothyroxine has no significant effect on high-density lipoproteins (HDL). Inherently, it will also bind to thyroid receptors and as it is a prohormone, it will bind as a substrate to iodide peroxidase.
Cellular LocationsCytoplasm
Applications
UsesOne of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroid hormone, but has been used to treat hyperlipidemia.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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