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T2877

Sigma-Aldrich

3,3′,5-Triiodo-L-thyronine

≥95% (HPLC), powder

Synonyma:

O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine, Liothyronine, T3

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About This Item

Empirický vzorec (Hillův zápis):
C15H12I3NO4
Číslo CAS:
6893-02-3
Molekulová hmotnost:
650.97
Beilstein/REAXYS Number:
2710227
EC Number:
229-999-3
MDL number:
MFCD00002593
UNSPSC Code:
51111800
PubChem Substance ID:
24900088
NACRES:
NA.32

biological source

synthetic (organic)

sterility

non-sterile

assay

≥95% (HPLC)

form

powder

optical activity

[α]25/D +23.0°, c = 2 in 1 N HCl: ethanol, 1:2

technique(s)

transfection: suitable

mp

234-238 °C (lit.)

solubility

4 M NH4OH in methanol: 5 mg/mL, clear to very slightly hazy, colorless to light yellow

shipped in

ambient

storage temp.

−20°C

SMILES string

N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(O)=O

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

InChI key

AUYYCJSJGJYCDS-LBPRGKRZSA-N

Gene Information

human ... THRA(7067) , THRB(7068)
rat ... Thra(81812) , Thrb(24831)

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Application

3,3′,5-Triiodo-L-thyronine can be used for Insulin-like growth factor I assays performed by using a double antibody radioimmunoassay. The product can also be used for in vitro transfection of 293T cells.

Biochem/physiol Actions

3,3′,5-Triiodo-L-thyronine also referred to as O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine or T3 is the biologically active thyroid hormone. In hypothyroidism pateints, triiodothyronine enhances mood and neuropsychological function. The product also positively regulates the hepatic FGF21 expression and stimulates the metabolic breakdown of glucose, fats, and proteins by enhancing the levels of numerous metabolic enzymes such as hexokinase, liver glucose 6-phosphatase as well as mitochondrial enzymes for oxidative phosphorylation. Additionally, the product facilitates the normal body growth in children and is pivotal for central nervous system maturation in foetus.

Preparation Note

3,3′,5-Triiodo-L-thyronine dissolves in 4M NH4OH in MeOH at 5 mg/ml to yield a colorless to light yellow, clear to very slightly hazy solution.

Other Notes

This product has not been tested for cell culture. A sterile version is offered that is suitable for cell culture. The T5516 is a sterile preparation that is cell culture tested. Please review the product page for product T2877

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1

target_organs

Thyroid,Cardio-vascular system,Kidney

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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Supelco

T-076

L-Thyroxine-13C6 solution

3,3′,5′-Triiodo-L-thyronine-13C6 solution 100 μg/mL in methanol with 0.1N NH3, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

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Sigma-Aldrich

T1775

L-Thyroxine

W A Head et al.
Journal of animal science, 74(9), 2152-2157 (1996-09-01)
Targhee ewes (n = 22, average age 5 yr) rearing twin lambs were used to investigate serum growth hormone (GH), IGF-I, triiodothyronine (T3), thyroxine (T4), and prolactin (PRL; ewes only) concentrations associated with selection pressure for lifetime production of kilograms
Soledad Bárez-López et al.
PloS one, 14(12), e0226017-e0226017 (2019-12-07)
Patients lacking the thyroid hormone (TH) transporter MCT8 present abnormal serum levels of TH: low thyroxine and high triiodothyronine. They also have severe neurodevelopmental defects resulting from cerebral hypothyroidism, most likely due to impaired TH transport across the brain barriers.
Andrew C Adams et al.
The Journal of biological chemistry, 285(19), 14078-14082 (2010-03-20)
Thyroid hormone has profound and diverse effects on liver metabolism. Here we show that tri-iodothyronine (T3) treatment in mice acutely and specifically induces hepatic expression of the metabolic regulator fibroblast growth factor 21 (FGF21). Mice treated with T3 showed a
R Bunevicius et al.
The New England journal of medicine, 340(6), 424-429 (1999-02-11)
Patients with hypothyroidism are usually treated with thyroxine (levothyroxine) only, although both thyroxine and triiodothyronine are secreted by the normal thyroid gland. Whether thyroid secretion of triiodothyronine is physiologically important is unknown. We compared the effects of thyroxine alone with
Takahiro Nojiri et al.
Endocrine journal, 66(5), 409-422 (2019-03-01)
Graves' Disease is a representative autoimmune thyroid disease that presents with hyperthyroidism. Emerging evidence has shown the involvement of lysophosphatidic acid (LPA) and its producing enzyme, autotaxin (ATX), in the pathogenesis of various diseases; among them, the involvement of the
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