16874-12-7

Basic information

• Product Name: tert-Butyl L-tyrosinate
• Synonyms: tert-butyl l-tyrosinate;TYROSINE-OTBU;H-TYR-OBUT;H-TYR-OTBU;L-TYROSINE T-BUTYL ESTER;L-TYROSINE TERT-BUTYL ESTER;2-Amino-3-(4-hydroxy-phenyl)-propionic acid tert-butyl ester;Tyr-OtBu
• CAS NO: 16874-12-7
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.29
• EINECS: 240-902-3
• Product Categories: chiral;Miscellaneous;Amino Acids;Tyrosine [Tyr, Y];Amino Acids and Derivatives;Amino Acid tert-Butyl Esters;Amino Acids (C-Protected);Biochemistry;Amino ester;Amino Acid Derivatives;Amino Acids;I - ZPeptide Synthesis;Modified Amino Acids;Tyrosine
• Mol File: 16874-12-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 141-144 °C
• Boiling Point: 358.1 °C at 760 mmHg
• Flash Point: 170.4 °C
• Appearance: White/Powder
• Density: 1.125 g/cm³
• Vapor Pressure: 1.26E-05mmHg at 25°C
• Refractive Index: 25 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 9.80±0.15(Predicted)
• BRN: 2696011
• CAS DataBase Reference: tert-Butyl L-tyrosinate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl L-tyrosinate(16874-12-7)
• EPA Substance Registry System: tert-Butyl L-tyrosinate(16874-12-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 16874-12-7(Hazardous Substances Data)

Usage

Description

t-Butyl L-tyrosinate, also known as L-Tyrosine tert-butyl ester, is a protected form of the essential amino acid L-Tyrosine. It is characterized by its crystalline chemical properties and exhibits in vitro antioxidant and antiradical activities. tert-Butyl L-tyrosinate serves as a crucial precursor in the synthesis of various biologically significant molecules, including catecholamines, proteins, and thyroid hormones.

Uses

Used in Pharmaceutical Industry:
t-Butyl L-tyrosinate is used as a precursor for the synthesis of catecholamines, such as Norepinephrine HCl, which play a vital role in the human body's response to stress and are involved in various physiological processes. This application is particularly relevant in the development of treatments for conditions related to the sympathetic nervous system.
Used in Protein Synthesis:
t-Butyl L-tyrosinate is utilized as a building block in the synthesis of proteins, which are essential macromolecules that perform a wide range of functions in living organisms. The incorporation of this amino acid ester into proteins can contribute to their structure, stability, and function.
Used in Thyroid Hormone Synthesis:
t-Butyl L-tyrosinate is also used as a precursor in the production of thyroid hormones, which are critical for regulating metabolism, growth, and development in the human body. The synthesis of these hormones using t-Butyl L-tyrosinate can be beneficial in the treatment of thyroid-related disorders and maintaining overall health.
Used in Antioxidant and Antiradical Applications:
Due to its in vitro antioxidant and antiradical properties, t-Butyl L-tyrosinate can be employed in the development of compounds that protect cells from oxidative stress and damage. This application can be particularly useful in the fields of nutrition, cosmetics, and pharmaceuticals, where the prevention of oxidative damage is of significant importance.

InChI:InChI=1/C13H19NO3/c1-13(2,3)17-12(16)11(14)8-9-4-6-10(15)7-5-9/h4-7,11,15H,8,14H2,1-3H3/t11-/m0/s1

Upstream product

• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 133852-23-0 tert-butyl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate 
• 112883-29-1 N-Fmoc-Tyr-OH 
• 60-18-4 L-tyrosine 
• 67-56-1 methanol 
• 540-88-5 acetic acid tert-butyl ester 
• 88878-78-8 tyrosine tert-butyl ester 
• 1164-16-5 Z-L-Tyr-OH 
• 1027921-22-7 2-(benzhydrylidene-amino)-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester 
• 217172-40-2 (S)-2-amino-3-(4-benzyloxy-phenyl)-tert-butyl-propionic ester 
• 16881-33-7 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate 
• 115-11-7 isobutene 
• 5544-60-5 4-(benzyloxy)benzyl bromide 

Downstream Products

• 100102-89-4 Z-Val-Tyr-OBu^t 
• 142822-20-6 N-benzyloxycarbonyl-L-seryl-L-tyrosine tert-butyl ester 
• 178271-91-5 (S)-2-Benzyloxycarbonylamino-N-[(S)-1-tert-butoxycarbonyl-2-(4-hydroxy-phenyl)-ethyl]-succinamic acid benzyl ester 
• 192822-99-4 N,N-dibenzyltyrosine tert-butyl ester 
• 67932-53-0 5,7-dinitroindoline 
• 16881-33-7 (S)-tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-(4-hydroxyphenyl)propanoate hydrate 
• 753489-21-3 C₇F₁₅CH₂TyrOBut 
• 51952-40-0 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycine amide hydrochloride 
• 142822-21-7 L-seryl-L-tyrosine tert-butyl ester 
• 51871-39-7 L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosine methyl ester 
• 142822-22-8 L-pyroglutamyl-L-histidyl-L-trypthophyl-L-seryl-L-tyrosine tert-butyl ester 
• 52434-75-0 pGlu-His-Trp-Ser-Tyr 

Relevant articles and documents

Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids

We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C-H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first time, C-H oxidation of N-allyl-protected amino acids to furnish five-membered heterocycles through 1,3-syn-addition is established with excellent diastereoselectivity.

A Bioinspired Synthesis of Polyfunctional Indoles

Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.

A novel SWCNT platform bearing DOTA and β-cyclodextrin units. "one shot" multidecoration under microwave irradiation

The functionalization of single-walled carbon nanotubes (SWCNTs) via microwave-assisted grafting reactions enables efficient multidecoration in a single step. A novel water-soluble SWCNT platform was prepared via the simple 1,3-dipolar cycloaddition of azomethine ylides under dielectric heating. Thanks to a single grafting reaction the CNT surface binds in a 1:1 ratio an amino acidic β-cyclodextrin (β-CD) derivative and the DOTAMA moiety (1,4,7,10-tetraazacyclododecane-N,N′,N′′,N′′ ′-tetraacetic acid monoamide). This novel "one shot" synthesis, compared with multistep functionalizations, preserves the SWCNT's structural integrity (TEM images). Besides thermogravimetric analyses, the determination of the amount of β-CD and DOTA moieties grafting onto the SWCNT's surface was performed on the basis of phenolphthalein and gadolinium complexation, respectively. This journal is