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Merck

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
UNSPSC Code:
41116107
NACRES:
NA.26
PubChem Substance ID:
24893248
EC Number:
213-867-7
Beilstein/REAXYS Number:
2707891
MDL number:
MFCD00064987

Key Documents

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InChI key

ZHSOTLOTTDYIIK-ZDUSSCGKSA-N

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

SMILES string

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

assay

≥99% (HPLC)

form

powder

technique(s)

ligand binding assay: suitable

color

white to off-white

mp

255 °C

storage temp.

−20°C

Quality Level

200

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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

WGK 3

ppe

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

D0629-5G:4548173996233 + D0629-VAR: + D0629-1G: + D0629-500MG:4548173996226 + D0629-BULK: + D0629-100MG:

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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
Pieter de Lange et al.
Diabetes, 60(11), 2730-2739 (2011-09-20)
High-fat diets (HFDs) are known to induce insulin resistance. Previously, we showed that 3,5-diiodothyronine (T2), concomitantly administered to rats on a 4-week HFD, prevented gain in body weight and adipose mass. Here we investigated whether and how T2 prevented HFD-induced
Alessandro Cavallo et al.
PloS one, 8(1), e52328-e52328 (2013-01-12)
Growing evidence shows that, among triiodothyronine derivatives, 3,5 diiodo-L-thyronine (T(2)) plays an important role in energy metabolism and fat storage. In the present study, short-term effects of T(2) administration to hypothyroid rats on fatty acid oxidation rate and bioenergetic parameters
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
Guoguo Shang et al.
Biochimica et biophysica acta, 1832(5), 674-684 (2013-02-19)
3, 5-Diiodothyronine (T2), a natural metabolite of triiodothyronine (T3) from deiodination pathway, can mimic biologic effects of T3 without inducing thyrotoxic effects. Recent studies revealed T3 acted as a protective factor against diabetic nephropathy (DN). Nevertheless, little is known about
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