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6893-02-3

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6893-02-3 Usage

Description

Crystalline T3 (liothyronine sodium, Cytomel) has a rapid onset and short duration of action. It is the therapy of choice when it is desirable to have rapid onset or cessation of activity, such as in patients with heart disease.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 6893-02-3 differently. You can refer to the following data:
1. 3,3’,5-Triiodo-L-thyronine (Levothyroxine EP Impurity A) is one of the hormones produced by the thyroid gland that is involved in the maintenance of metabolic homeostasis. Also produced in peripheral tissues as the active metabolite of Thyroxine.
2. T3 or 3,3',5-Triiodo-L-thyronine is a thyroid hormone involved with many physiological processes in the human body including growth and development, metabolism, body temperature and heart rate. Free and total T3 serum levels are measured by LC-MS/MS for determination of hyperthyroidism caused by excess T3. This Certified Spiking Solution? is suitable for use as a starting material in preparation of linearity standards, calibrators, and controls for thyroid hormone testing methods by LC-MS/MS.

Definition

ChEBI: An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxi e in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism.

Application

3,3′,5′-Triiodo-L-thyronine (T3) is an endocrine hormone produced by the thyroid gland and is regarded as an active thyroid hormone at cellular level. Thyroxine (T4) serves as a precursor for T3 and is generated in extrathyroidal tissues.3,3′,5-Triiodo-L-thyronine sodium salt has been used for inducing thyroid hormone manipulations in mice. It has also been used In cell culturing of hippocampal, retinal, proximal tubule and glomerular explant.

Biological Activity

3,3′,5′-Triiodo-L-thyronine (T3) increases the rates of protein synthesis, stimulates the breakdown of cholesterol and effects embryonic development. In cell culture, T3 regulates cell differentiation and protein expression. The interaction of T3 with nonhistone proteins in the chromatin initiates the thyroid hormone activity. Thyroid hormones regulate the differentiation and development of tissues and affect a number of metabolic processes. The level of circulating T3 hormone is reduced in hypothyroidism.

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.

Purification Methods

Likely impurities are as in thyroxine. Purify it by dissolving in dilute NH3 at ~20o, then crystallise it by addition of dilute acetic acid to pH 6. Alternatively 35g are purified by dissolving it in a mixture of EtOH (250mL) and 2N NaOH (100mL), then hot 2N HCl is added to the boiling solution until the pH is 4-5. After cooling for a few hours, the solid is filtered off and dried in a vacuum [m 233-235o(dec)]. [Chambers et al. J Chem Soc 2433 1949, Beilstein 14 III 1566, 14 IV 2373.]

Check Digit Verification of cas no

The CAS Registry Mumber 6893-02-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,8,9 and 3 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 6893-02:
(6*6)+(5*8)+(4*9)+(3*3)+(2*0)+(1*2)=123
123 % 10 = 3
So 6893-02-3 is a valid CAS Registry Number.

6893-02-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Price
  • Detail
  • TCI America

  • (T0453)  3,3',5-Triiodo-L-thyronine  >98.0%(HPLC)(T)

  • 6893-02-3

  • 100mg

  • 435.00CNY

  • Detail
  • Alfa Aesar

  • (H34068)  3,3',5-Triiodo-L-thyronine, 95%   

  • 6893-02-3

  • 250mg

  • 687.0CNY

  • Detail
  • Alfa Aesar

  • (H34068)  3,3',5-Triiodo-L-thyronine, 95%   

  • 6893-02-3

  • 1g

  • 1909.0CNY

  • Detail
  • Alfa Aesar

  • (H34068)  3,3',5-Triiodo-L-thyronine, 95%   

  • 6893-02-3

  • 5g

  • 7059.0CNY

  • Detail

6893-02-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,3',5-triiodo-L-thyronine

1.2 Other means of identification

Product number -
Other names 3,3',5 TRIIODOTHYRONINE (T3), IRMM STANDARD

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6893-02-3 SDS

6893-02-3Synthetic route

3,5-diiodo-l-tyrosine

3,5-diiodo-l-tyrosine

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

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

triiodothyronine
6893-02-3

triiodothyronine

triiodothyronine
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

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

triiodothyronine
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
thyroxine
300-30-1

thyroxine

triiodothyronine
6893-02-3

triiodothyronine

liothyronine sodium
55-06-1

liothyronine sodium

triiodothyronine
6893-02-3

triiodothyronine

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

triiodothyronine

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

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%
triiodothyronine
6893-02-3

triiodothyronine

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

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%
triiodothyronine
6893-02-3

triiodothyronine

L-Triiodothyronine sulfate

L-Triiodothyronine sulfate

Conditions
ConditionsYield
With chlorosulfonic acid; trifluoroacetic acid at 0℃; for 0.166667h;25%
5-(dimethylamino)naphth-1-ylsulfonyl chloride
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

triiodothyronine
6893-02-3

triiodothyronine

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

(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
tert-butyl N-{2-[(2,5-dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}carbamate
3392-07-2

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

triiodothyronine
6893-02-3

triiodothyronine

Boc-Gly-T3

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
C13H13NSSe
1261501-03-4

C13H13NSSe

triiodothyronine
6893-02-3

triiodothyronine

A

C13H15NSSe
1261500-99-5

C13H15NSSe

B

L-3,3'-Diiodothyronine
70-40-6, 58342-32-8, 4604-41-5

L-3,3'-Diiodothyronine

Conditions
ConditionsYield
With DL-dithiothreitol at 37℃; pH=7.5; aq. phosphate buffer; regioselective reaction;
C10H8SSe
903571-91-5

C10H8SSe

triiodothyronine
6893-02-3

triiodothyronine

A

naphtho<1,8-cd>thiaselenole
64869-35-8

naphtho<1,8-cd>thiaselenole

B

L-3,3'-Diiodothyronine
70-40-6, 58342-32-8, 4604-41-5

L-3,3'-Diiodothyronine

Conditions
ConditionsYield
With DL-dithiothreitol at 37℃; pH=7.5; aq. phosphate buffer; regioselective reaction;
triiodothyronine
6893-02-3

triiodothyronine

A

3'-Iodothyronine
4732-82-5

3'-Iodothyronine

B

3-Monoiodothyronine
10468-90-3

3-Monoiodothyronine

C

O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine
1596-67-4

O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: D,L-dithiothreitol; sodium tetrahydroborate; C10H8STe / aq. phosphate buffer / 0.5 h / 37 °C / pH 7.5
2: D,L-dithiothreitol; sodium tetrahydroborate; C10H8STe / aq. phosphate buffer / 0.5 h / 37 °C / pH 7.5
View Scheme
Multi-step reaction with 2 steps
1: D,L-dithiothreitol; sodium tetrahydroborate; C10H8STe / aq. phosphate buffer / 0.5 h / 37 °C / pH 7.5
2: D,L-dithiothreitol; sodium tetrahydroborate; C10H8STe / aq. phosphate buffer / 0.5 h / 37 °C / pH 7.5
View Scheme
triiodothyronine
6893-02-3

triiodothyronine

3,5-diiodo-N-[[(carboxymethyl)[2-[(carboxymethyl)[2-[bis(carboxymethyl)amino]ethyl]amino]ethyl]amino]acetyl]-O-[3-iodo-4-(sulfooxy)phenyl]-l-tyrosine

3,5-diiodo-N-[[(carboxymethyl)[2-[(carboxymethyl)[2-[bis(carboxymethyl)amino]ethyl]amino]ethyl]amino]acetyl]-O-[3-iodo-4-(sulfooxy)phenyl]-l-tyrosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chlorosulfonic acid / N,N-dimethyl acetamide / 4.67 h / -5 - 5 °C / Inert atmosphere
1.2: 1.5 h / Inert atmosphere
2.1: N,N-dimethyl acetamide; water / 4.5 h / 80 °C
2.2: 0.33 h / 25 °C
View Scheme
triiodothyronine
6893-02-3

triiodothyronine

C36H47I3N4O14S2

C36H47I3N4O14S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: chlorosulfonic acid / N,N-dimethyl acetamide / 4.67 h / -5 - 5 °C / Inert atmosphere
1.2: 1.5 h / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 0 - 20 °C
View Scheme
Tetrabromophthalic anhydride
632-79-1

Tetrabromophthalic anhydride

triiodothyronine
6893-02-3

triiodothyronine

C23H12Br4I3NO7

C23H12Br4I3NO7

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 0.75h;
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

triiodothyronine
6893-02-3

triiodothyronine

NH2-T3-OtBu

NH2-T3-OtBu

Conditions
ConditionsYield
With perchloric acid at 0 - 20℃; for 16h;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

triiodothyronine
6893-02-3

triiodothyronine

Boc-T3-OH

Boc-T3-OH

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20 - 30℃; for 30.5h;

6893-02-3Relevant articles and documents

A cell-penetrating artificial metalloenzyme regulates a gene switch in a designer mammalian cell

Okamoto, Yasunori,Kojima, Ryosuke,Schwizer, Fabian,Bartolami, Eline,Heinisch, Tillmann,Matile, Stefan,Fussenegger, Martin,Ward, Thomas R.

, (2018/05/24)

Complementing enzymes in their native environment with either homogeneous or heterogeneous catalysts is challenging due to the sea of functionalities present within a cell. To supplement these efforts, artificial metalloenzymes are drawing attention as they combine attractive features of both homogeneous catalysts and enzymes. Herein we show that such hybrid catalysts consisting of a metal cofactor, a cell-penetrating module, and a protein scaffold are taken up into HEK-293T cells where they catalyze the uncaging of a hormone. This bioorthogonal reaction causes the upregulation of a gene circuit, which in turn leads to the expression of a nanoluc-luciferase. Relying on the biotin-streptavidin technology, variation of the biotinylated ruthenium complex: the biotinylated cell-penetrating poly(disulfide) ratio can be combined with point mutations on streptavidin to optimize the catalytic uncaging of an allyl-carbamate-protected thyroid hormone triiodothyronine. These results demonstrate that artificial metalloenzymes offer highly modular tools to perform bioorthogonal catalysis in live HEK cells.

3, 5-diiodo-O-[ 3-phenyl]-production of sulfate derivative of L-thyrosine (by machine translation)

-

Paragraph 0060, (2017/01/05)

The present invention relates to a process for the preparation of the mono sodium salt of the derivative 3,5-diiodo-O-[3-iodo-4-(sulphooxy)phenyl]-L- tyrosine (T3S) by starting from the corresponding phenolic compound, in the presence of chlorosulfonic acid and dimethylacetamide as a solvent. The so obtained T3S compound may conveniently be isolated in a pure form as a solid in good yields. The present invention further relates to the process for T3S preparation, wherein the starting reagent is T2 and further comprising the formulation of such compound in tablets. Furthermore, the invention discloses non-radioactive immunoassays based on T3S derivatives.

A concise synthesis of thyroxine (T4) and 3,5,3'-Triiodo-L-thyronine (T3)

Salamonczyk, Grzegorz M.,Oza, Vibha B.,Sih, Charles J.

, p. 6965 - 6968 (2007/10/03)

The mono- and di-iodo derivatives of 1-oxaspiro[2,5]bicycloocta-4,7-dien-6-one, 8 and 9, reacted readily with 3,5-diiodo-L-tyrosine at pH 8.0 to give 3,5,3'-triiodo-L-thyronine (T3) and thyroxine in 70% and 94% yields respectively. In turn, 8 and 9 were prepared by the sodium bismuthate oxidation of their corresponding iodinated p-hydroxybenzyl alcohol derivatives, 6 and 7 in 32% and 37% yields.

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