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T1775

L-Thyroxine

Name: <SC>L</SC>-Thyroxine
Brand: SIGMA

powder, BioReagent, suitable for cell culture

Synonym(s):

3,3′,5,5″-Tetraiodo-L-thyronine, 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine, T₄

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About This Item

Linear Formula:

HOC₆H₂(I)₂OC₆H₂(I)₂CH₂CH(NH₂)CO₂H

CAS Number:

51-48-9

Molecular Weight:

776.87

Beilstein:

2228515

EC Number:

200-101-1

MDL number:

MFCD00002595

UNSPSC Code:

12352209

eCl@ss:

32190102

PubChem Substance ID:

24899990

NACRES:

NA.77

biological source

synthetic

Quality Level

200

product line

BioReagent

Assay

≥98% (HPLC)

form

powder

potency

5-50 ng/mL

technique(s)

cell culture | mammalian: suitable

mp

223 °C (dec.) (lit.)

solubility

4 M NH₄OH in methanol: 50 mg/mL, clear to hazy, yellow

shipped in

ambient

storage temp.

room temp

SMILES string

N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O

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

InChI key

XUIIKFGFIJCVMT-LBPRGKRZSA-N

Gene Information

human ... THRA(7067) , THRB(7068) , TTR(7276)
mouse ... Cnr2(12802)
rat ... Cnr1(25248)

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Related Categories

Hormones

General description

Thyroxine (T₄) is a tetraiodo derivative of the p-hydroxyphenyl ether of tyrosine, which functions as growth factors or cell growth inhibitors. T₄ is used to treat hypothyroidism and thyroid carcinoma. It regulates energy metabolism.

Application

L-Thyroxine has been used to investigate its role in colorectal cancer cell lines HCT 116 (APC wild type) and HT-29 (APC mutant). It has also been used to evaluate its effects on pro-inflammatory tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6), angiogenic vascular endothelial growth factor (VEGF), leukocyte adhesion, intercellular adhesion molecule 1 (ICAM-1) and E-selectin in human umbilical vein endothelial cells (HUVECs).

Biochem/physiol Actions

L-Thyroxine (T₄) and triiodo-L-thyronine (T₃) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.

Preparation Note

For long term storage, keep stock solutions at -20° in working aliquots and avoid repeated freeze/thaw cycles. Solutions stored at 2-8 °C are stable for up to 30 days.

Reconstitution

To prepare 20 μg/ml stock solution, dissolve in 50 ml sterile culture medium per mg thyroxine.

Pictograms

GHS08

Signal Word

Danger

Hazard Statements

H372

Precautionary Statements

P260 - P264 - P270 - P314 - P501

Hazard Classifications

STOT RE 1

Target Organs

Thyroid,Cardio-vascular system,Kidney

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)