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Merck
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Key Documents

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D0629

Sigma-Aldrich

3,5-Diiodo-L-thyronine

thyroid hormone analog

Sinónimos:

3,5-Diiodo-4-(4-hydroxyphenoxy)-L-phenylalanine, 3,5-T2, O-(4-Hydroxyphenyl)-3,5-diiodo-L-tyrosine

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About This Item

Fórmula empírica (notación de Hill):
C15H13I2NO4
Número de CAS:
1041-01-6
Peso molecular:
525.08
Beilstein/REAXYS Number:
2707891
EC Number:
213-867-7
MDL number:
MFCD00064987
UNSPSC Code:
41116107
PubChem Substance ID:
24893248
NACRES:
NA.26

Quality Level

200

assay

≥99% (HPLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white to off-white

mp

255 °C

storage temp.

−20°C

SMILES string

N[C@@H](Cc1cc(I)c(Oc2ccc(O)cc2)c(I)c1)C(O)=O

InChI

1S/C15H13I2NO4/c16-11-5-8(7-13(18)15(20)21)6-12(17)14(11)22-10-3-1-9(19)2-4-10/h1-6,13,19H,7,18H2,(H,20,21)/t13-/m0/s1

InChI key

ZHSOTLOTTDYIIK-ZDUSSCGKSA-N

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Biochem/physiol Actions

3,5-Diiodo-L-thyronine ((T(2)) is an iodinated thyronine hormone that regulates gene activity affecting processes such as homeostasis, lipid metabolism and insulin resistance.

hcodes

H412

Hazard Classifications

Aquatic Chronic 3

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Maria Moreno et al.
Thyroid : official journal of the American Thyroid Association, 18(2), 239-253 (2008-02-19)
The processes and pathways mediating the intermediary metabolism of carbohydrates, lipids, and proteins are all affected by thyroid hormones (THs) in almost all tissues. Particular attention has been devoted by scientists to the effects of THs on lipid metabolism. Among
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.
Alessio Rochira et al.
Biochimica et biophysica acta, 1831(12), 1679-1689 (2013-08-21)
Thyroid hormone 3,5,3'-triiodo-l-thyronine (T3) is known to affect cell metabolism through both the genomic and non-genomic actions. Recently, we demonstrated in HepG2 cells that T3 controls the expression of SREBP-1, a transcription factor involved in the regulation of lipogenic genes.
Roberto Mangiullo et al.
Biochimica et biophysica acta, 1797(2), 233-240 (2009-11-03)
Besides triiodothyronine (T3), 3,5-diiodo-L-thyronine (T2) has been reported to affect mitochondrial bioenergetic parameters. T2 effects have been considered as independent of protein synthesis. Here, we investigated the effect of in vivo chronic T2 administration to hypothyroid rats on liver mitochondrial
Anna M Giudetti et al.
Endocrinology, 146(9), 3959-3966 (2005-06-04)
Short-term effects of 3,5-l-diiodothyronine (T2) on lipid biosynthesis were studied in cultured hepatocytes from hypothyroid rats. A comparison with the effects of T3 was routinely carried out. After T2 addition to cell cultures, a distinct stimulation of fatty acid and
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