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D0629

Sigma-Aldrich

3,5-Diiodo-L-thyronine

thyroid hormone analog

Synonym(s):

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

Empirical Formula (Hill Notation):
C15H13I2NO4
CAS Number:
1041-01-6
Molecular Weight:
525.08
Beilstein:
2707891
EC Number:
213-867-7
MDL number:
MFCD00064987
UNSPSC Code:
41116107
PubChem Substance ID:
24893248
NACRES:
NA.26

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.

Hazard Statements

H412

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

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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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
C J Huang et al.
Journal of molecular and cellular cardiology, 31(4), 881-893 (1999-05-18)
We previously reported that T3(3,3',5-triiodo-L-thyronine) acutely increases sodium currents (INa) in neonatal rat myocytes. Here we compare the effects of several thyroid hormone analogs, including T4(3,3',5,5'-tetraiodo-L-thyronine), rT3(3,3',5'-triiodo-L-thyronine), D-T3(3,3',5-triiodo-D-thyronine), 3,5-T2(3,5-diiodo-L-thyronine), DIT (3,5-diiodo-L-tyrosine), MIT (3-monoiodo-L-tyrosine), tetrac (3,3',5,5'-tetraiodo-thyroacetic acid), triac (3, 3',5-triiodo-thyroacetic acid)
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
Maria Moreno et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 25(10), 3312-3324 (2011-06-15)
The worldwide prevalence of obesity-associated pathologies, including type 2 diabetes, requires thorough investigation of mechanisms and interventions. Recent studies have highlighted thyroid hormone analogs and derivatives as potential agents able to counteract such pathologies. In this study, in rats receiving
Elena Grasselli et al.
Journal of hepatology, 54(6), 1230-1236 (2010-12-15)
Previous studies have demonstrated that 3,5-L-diiodothyronine (T(2)) is able to prevent lipid accumulation in the liver of rats fed a high-fat diet. Whether this effect is due to a direct action of T(2) on the liver has not been elucidated.
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