1041-01-6

Basic information

• Product Name: 3,5-Diiodo-L-thyronine
• Synonyms: 3,5-Diiodi-L-thyronine;3,5-DIIODO-L -THYRONINE 98%;3,5-Diiodo-4-(4-hydroxyphenoxy)-L-phenylalanine, O-(4-Hydroxyphenyl)-3,5-diiodo-L-tyrosine;3,5-Diiodo-O-(4-hydroxyphenyl)-L-tyrosine;L-Diiodothyronine;Alanine, 3-[4-(p-hydroxyphenoxy)-3,5-diiodophenyl]-, L-;Diiodo-L-thyronine;L-3,5-Diiodothyronine
• CAS NO: 1041-01-6
• Molecular Formula: C₁₅H₁₃I₂NO₄
• Molecular Weight: 525.08
• EINECS: 213-867-7
• Product Categories: Medicine intermediate;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Intermediates;Labeling and Diagnostics Reagents
• Mol File: 1041-01-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 255-260 °C (dec.)
• Boiling Point: 559.4 °C at 760 mmHg
• Flash Point: 292.1 °C
• Appearance: Off-white solid
• Density: 2.095 g/cm³
• Vapor Pressure: 2.39E-13mmHg at 25°C
• Refractive Index: 1.726
• Storage Temp.: 2-8°C
• Solubility: Acidic Alcohol (Slightly), Aqueous Base (Slightly)
• PKA: 2.15±0.30(Predicted)
• Water Solubility: 20.147mg/L at 20℃
• Stability: Hygroscopic
• BRN: 2707891
• CAS DataBase Reference: 3,5-Diiodo-L-thyronine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diiodo-L-thyronine(1041-01-6)
• EPA Substance Registry System: 3,5-Diiodo-L-thyronine(1041-01-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 1041-01-6(Hazardous Substances Data)

Usage

Chemical Properties

[α] 25 D +25.2° [5 % solution in 1 M HCl:95 % ethanol (1:2)], off-White Solid.

Uses

Different sources of media describe the Uses of 1041-01-6 differently. You can refer to the following data:
1. 3,5-Diiodo-L-thyronine is an iodinated thyronine hormone that regulates gene activity affecting processes such as homeostasis, lipid metabolism and insulin resistance.
2. Of interest for the early detection and treatment of congenital or drug-induced hypothyroidism.

Flammability and Explosibility

Notclassified

Pharmacology

3,5-Diiodo-L-thyronine is a?thyroid hormone with a l-thyroxine-like activity.

Purification Methods

Recrystallise it from EtOH. [Chambers et al. J Chem Soc 3424 1949, Beilstein 14 II 226, 14 III 1565, 14 IV 2372.]

InChI:InChI=1/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)

Upstream product

• 94298-44-9 N-formyl-3,5-diiodo-L-thyronine 
• 21959-36-4 N-acetyl-3,5-diiodo-L-tyrosine ethyl ester 
• 1027-28-7 N-acetyl-3,5-diiodo-L-tyrosine 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 83249-56-3 N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester 
• 19231-06-2 4,4'-dimethoxy-diphenyliodonium bromide 
• 94345-95-6 2-amino-3-(3,5-diiodo-4-(4-methoxyphenoxy)phenyl)propanoic acid 
• 49553-16-4 {Cu(HOC₆H₂I₂CH₂CH(NH₂)COO)2} 
• 51-48-9 L-thyroxine 
• 128781-80-6 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3,5-diiodophenyl)propanoate 
• 4326-36-7 (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester 
• 1080-06-4 L-Tyr-OMe 
• 60-18-4 L-tyrosine 
• 623-05-2 (4-hydroxyphenyl)methanol 

Downstream Products

• 55-06-1 liothyronine sodium 
• 10468-90-3 3-Monoiodothyronine 
• 1596-67-4 O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine 
• 1417654-00-2 (S)-tert-butyl (1-hydroxy-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propan-2-yl)carbamate 
• 1417654-30-8 (S)-4-(4-(4-hydroxyphenoxy)-3,5-diiodobenzyl)imidazolidin-2-one 
• 1417654-28-4 (S)-1-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)-3-hexylurea 
• 1417654-25-1 (S)-1-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)-3-benzylurea 
• 1417654-20-6 (S)-N-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)-2-hydroxyacetamide 
• 1417654-17-1 (S)-N-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)-3-morpholinopropanamide 
• 1417654-15-9 (S)-N-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)morpholine-4-carboxamide 
• 1417654-13-7 (S)-1-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)-3-isopropylurea 
• 1417654-09-1 (S)-N-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)methanesulfonamide 
• 1417654-08-0 (S)-N-(2-amino-3-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)propyl)acetamide 
• 1417654-06-8 (S)-4-(4-(2,3-diaminopropyl)-2,6-diiodophenoxy)phenol 

Related news

Direct and rapid effects of 3,5-Diiodo-L-thyronine (cas 1041-01-6) (T2)07/22/2019

A growing number of researchers are focusing their attention on the possibility that thyroid hormone metabolites, particularly 3,5-diiodothyronine (T2), may actively regulate energy metabolism at the cellular, rather than the nuclear, level. Due to their biochemical features, mitochondria have b...detailed

Relevant articles and documents

Preparation method of levothyroxine sodium

The invention belongs to the field of pharmaceutical synthesis, and discloses a preparation method of levothyroxine sodium. The preparation method comprises the following steps: (1) taking 3,5-diiodo-L-tyrosine as a raw material, and preparing N-acetyl-L-tyrosine by firstly introducing acetyl protection to an amino group; (2) then preparing N-acetyl-3,5-diiodo-L-tyrosine ethyl ester under the action of thionyl chloride; (3) preparing N-acetyl-O-(4-methyoxyphenyl)-3,3-diiodo-L-tyrosine ethyl ester by carrying out Chan-Lam reaction through copper catalysis; (4) removing a protective group undera strong acidity condition, thus obtaining O-(4-hydroxyphenyl)-3,5-diiodo-L-tyrosine; (5) then reacting with iodine, and preparing O-(4-hydroxy-3,5-diiodo phenyl)-3,5-diiodo-L-tyrosine disodium salt under the action of sodium hydroxide; (6) finally, regulating pH (Potential of Hydrogen) through glacial acetic acid, thus obtaining the levothyroxine sodium. According to the preparation method disclosed by the invention, the key Chan-Lam reaction and other reaction steps are optimized, so that the reaction time can be greatly shortened, and the reaction yield can be increased; the preparation method is simple in technology, convenient to operate and suitable for industrial production.

Reductive dehalogenation and dehalogenative sulfonation of phenols and heteroaromatics with sodium sulfite in an aqueous medium

Prototropic tautomerism was used as a tool for the reductive dehalogenation of (hetero)aryl bromides and iodides, or dehalogenative sulfonation of (hetero)aryl chlorides and fluorides, using sodium sulfite as the sole reagent in an aqueous medium. This protocol does not require a metal or phase transfer catalyst and avoids using organic solvent as the reaction medium. This method is especially suitable for substrates that readily tautomerize (such as 2-or 4-halogenated aminophenols and 4-halogenated resorcinols), for which dehalogenation or sulfonation proceeds under mild reaction conditions (≤60 °C). As sodium sulfite is an inexpensive, safe, and environmentally less hazardous reagent, this method has at least three potential applications: (i) in the deprotection of halogens as protecting groups, using sodium sulfite as a reducing agent; (ii) in the sulfonation of aromatic halides under mild reaction conditions avoiding hazardous and corrosive reagents/solvents; and (iii) in the transformation of toxic halogenated aromatics into less harmful compounds.

A concise synthesis of thyroxine (T4) and 3,5,3'-Triiodo-L-thyronine (T3)

The mono- and di-iodo derivatives of 1-oxaspiro[2,5]bicycloocta-4,7-dien-6-one, 8 and 9, reacted readily with 3,5-diiodo-L-tyrosine at pH 8.0 to give 3,5,3'-triiodo-L-thyronine (T3) and thyroxine in 70% and 94% yields respectively. In turn, 8 and 9 were prepared by the sodium bismuthate oxidation of their corresponding iodinated p-hydroxybenzyl alcohol derivatives, 6 and 7 in 32% and 37% yields.