1027-28-7

Basic information

• Product Name: N-Acetyl-3,5-diiodo-L-tyrosine
• Synonyms: N-ACETYL-3,5-DIIODO-L-TYROSINE;n-acetyl-3-5-diiodo-l-tyrosine1/2h2o*crystallin;3,5-DIIODO-N-ACETYL-L-TYROSINE;AC-3,5-DIIODO-TYR-OH;N-Acetyl-3,5-Diiodo-L-tyrosine dihydrate;N-ACETYL-3-5-DIIODO-L-TYROSINE 1/2 H2OCR YSTALLINE;3,5-Diiodo-N-acetyl-L-tyrodine;N-Acetyl-3,
• CAS NO: 1027-28-7
• Molecular Formula: C₁₁H₁₁I₂NO₄
• Molecular Weight: 475.02
• EINECS: 213-837-3
• Product Categories: A - H;Amino Acids;Modified Amino Acids
• Mol File: 1027-28-7.mol

Chemical Properties

• Melting Point: 124.0 to 128.0 °C
• Boiling Point: 532.9 °C at 760 mmHg
• Flash Point: 276.1 °C
• Appearance: /
• Density: 2.206 g/cm³
• Vapor Pressure: 3.47E-12mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: −20°C
• Solubility: almost transparency in Methanol
• PKA: 2.98±0.10(Predicted)
• CAS DataBase Reference: N-Acetyl-3,5-diiodo-L-tyrosine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-3,5-diiodo-L-tyrosine(1027-28-7)
• EPA Substance Registry System: N-Acetyl-3,5-diiodo-L-tyrosine(1027-28-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 1027-28-7(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
N-Acetyl-3,5-diiodo-L-tyrosine is used as a research compound for studying thyroid hormone biosynthesis. It aids in understanding the process of hormone production and its regulation within the body.
Used in Enzyme Studies:
N-Acetyl-3,5-diiodo-L-tyrosine is used as a substrate in enzyme studies, specifically to investigate the binding region of the active center of pepsin. This helps in understanding the enzyme's catalytic activity and its role in the hydrolysis process.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, N-Acetyl-3,5-diiodo-L-tyrosine could potentially be used in the pharmaceutical industry for the development of drugs targeting thyroid hormone-related disorders or for enhancing enzyme inhibition therapies.

InChI:InChI=1/C11H11I2NO4/c1-5(15)14-9(11(17)18)4-6-2-7(12)10(16)8(13)3-6/h2-3,9,16H,4H2,1H3,(H,14,15)(H,17,18)/t9-/m0/s1

Upstream product

• 96679-34-4 3.5-diiodo-N.O-diacetyl-L-tyrosine 
• 300-39-0 3,5-diiodo-l-tyrosine 
• 108-24-7 acetic anhydride 
• 60-18-4 L-tyrosine 
• 537-55-3 N-acetyl-L-tyrosine 

Downstream Products

• 21959-36-4 N-acetyl-3,5-diiodo-L-tyrosine ethyl ester 
• 51-48-9 L-thyroxine 
• 26041-51-0 (S)-2-acetamido-3-(4-(4-hydroxy-3,5-diaiodophenoxy)-3,5-diaiodophenyl)propanoic acid 
• 3604-71-5 3.5-diiodo-O-benzyl-N-acetyl-L-tyrosine 
• 88565-66-6 3.5-diiodo-O-methyl-N-acetyl-L-tyrosine 
• 64700-62-5 3.5-diiodo-O-(4-nitro-benzyl)-N-acetyl-L-tyrosine 
• 823176-18-7 3,5-diiodo-O-methyl-L-tyrosine 
• 83249-56-3 N-acetyl-O-(4-methoxyphenyl)-3,5-diiodo-L-tyrosine ethyl ester 
• 1041-01-6 3,5-diiodo-L-thyronine 
• 55-03-8 L-thyroxine sodium 

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.

Facile syntheses of 3-halo and mixed 3,5-dihalo analogues of N-acetyl-l-tyrosine via sulfonic acid-catalysed regioselective monohalogenation

The combination of catalytic amounts of p-toluenesulfonic acid and 1 equiv of N-halosuccinimide afforded highly selective ring-halogenation of N-acetyl-l-tyrosine, furnishing either N-acetyl-3-halo-l-tyrosine analogues or mixed 3,5-dihalo derivatives in a one-pot reaction with excellent yields at room temperature.