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Merck
CN

D0629

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

Key Documents

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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.

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

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ5652
MKCL2543
MKCB2257V
MKCB1817V
MKCB0274V

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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
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.
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.
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
Antonia Lanni et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 19(11), 1552-1554 (2005-07-15)
The effect of thyroid hormones on metabolism has long supported their potential as drugs to stimulate fat reduction, but the concomitant induction of a thyrotoxic state has greatly limited their use. Recent evidence suggests that 3,5-diiodo-L-thyronine (T2), a naturally occurring
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