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T0281

Sigma-Aldrich

3,3′,5′-Triiodo-L-thyronine

thyroid hormone analog

Synonym(s):

Reverse T3, rT(3)

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About This Item

Empirical Formula (Hill Notation):
C15H12I3NO4
CAS Number:
5817-39-0
Molecular Weight:
650.97
MDL number:
MFCD00036864
UNSPSC Code:
12352200
PubChem Substance ID:
24899878
NACRES:
NA.26

assay

≥97.0% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

storage temp.

−20°C

SMILES string

N[C@@H](Cc1ccc(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O

InChI

1S/C15H12I3NO4/c16-9-3-7(4-12(19)15(21)22)1-2-13(9)23-8-5-10(17)14(20)11(18)6-8/h1-3,5-6,12,20H,4,19H2,(H,21,22)/t12-/m0/s1

InChI key

HZCBWYNLGPIQRK-LBPRGKRZSA-N

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Application

3,3′,5′-Triiodo-L-thyronine has been used as a supplement in cell culture media for generation of oligodendrocyte lineage cells from human pluripotent stem cells. It has also been used as a supplement to culture epithelial tissue in vitro.

Biochem/physiol Actions

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. The interaction of T3 with nonhistone proteins in the chromatin initiates the thyroid hormone activity. Thyroid hormones regulate the differentiation and development of tissue and affect a number of metabolic processes. The level of circulating T3 hormone is reduced in hypothyroidism.
rT3 inhibits the increase of sodium current generated by other thyroid hormone analogs in neonatal rat myocytes. The ratio of triiodothryonine (T3) to rT3 has been investigated as in indicator of insulin resistance.

pictograms

Exclamation mark
GHS07

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Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Enrique Pimentel
Hormones Growth Factors & Oncogenes, 219-219 (1987)
An Jacobs et al.
Thyroid : official journal of the American Thyroid Association, 29(4), 480-492 (2019-02-15)
Non-thyroidal illness (NTI), which occurs with fasting and in response to illness, is characterized by thyroid hormone inactivation with low triiodothyronine (T3) and high reverse T3 (rT3), followed by suppressed thyrotropin (TSH). Withholding supplemental parenteral nutrition early in pediatric critical
Reporting on methods to generate and purify rodent and human oligodendrocytes from different sources
MehdiDjelloul
Stem Cell Research, 20, 58-66 (2017)
Victor R. Preedy
Handbook of Behavior, Food and Nutrition, 2109-2109 (2011)
Tatsuya Kunisue et al.
Analytical chemistry, 83(1), 417-424 (2010-12-03)
Thyroid hormones (THs) play critical roles in the regulation of growth and development, including brain development, in both humans and animals. Until recently, TH levels were assayed with measurements in serum, using immunoassay (IA)-based methods. IA methods are sensitive but
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