4089-07-0

Basic information

• Product Name: Ethyl L-tyrosinate hydrochloride
• Synonyms: (S)-2-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID ETHYL ESTER HCL;TEE;ethylester,hydrochloride,l-tyrosin;tyrosineethylesterhydrochloride;TYROSINE-OET HCL;L-TYROSINE ETHYL ESTER MONOHYDROCHLORIDE;L-TYROSINE ETHYL ESTER HYDROCHLORIDE SALT;L-TYROSINE ETHYL ESTER HYDROCHLORIDE
• CAS NO: 4089-07-0
• Molecular Formula: C₁₁H₁₅NO₃*ClH
• Molecular Weight: 245.7
• EINECS: 223-820-2
• Product Categories: Amino Acids;Tyrosine [Tyr, Y];Amino Acids and Derivatives;Amino Acid Ethyl Esters;Amino Acids (C-Protected);Biochemistry;Amino hydrochloride;Amino Acid Derivatives;Peptide Synthesis;Tyrosine;Amino Acids;I - ZPeptide Synthesis;Modified Amino Acids
• Mol File: 4089-07-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 166-170 °C
• Boiling Point: 343.3 °C at 760 mmHg
• Flash Point: 161.4 °C
• Appearance: crystalline
• Density: 1.177 g/cm3
• Vapor Pressure: 3.59E-05mmHg at 25°C
• Refractive Index: -6.5 ° (C=2, H2O)
• Storage Temp.: −20°C
• Water Solubility: Soluble in water (3.685e+005 mg/L @ 25°C (est.)).
• BRN: 4725904
• CAS DataBase Reference: Ethyl L-tyrosinate hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl L-tyrosinate hydrochloride(4089-07-0)
• EPA Substance Registry System: Ethyl L-tyrosinate hydrochloride(4089-07-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 2
• RTECS: YP2580000
• Hazardous Substances Data: 4089-07-0(Hazardous Substances Data)

Usage

Uses

L-Tyrosine Ethyl Ester Hydrochloride is used as a medical and organic intermediate and as an important amino protective agent. It is also used to introduce t-Boc protect gene.

Application

Papain is also used for synthesizing poly(L-tyrosine) and poly(L-glutamic acid) using L-tyrosine ethyl ester hydrochloride and L-glutamic acid diethyl ester hydrochloride as the substrates, respectively. The protease-catalyzed copolymerization of amino acids is first achieved by papain using L-glutamic acid ester and various amino acid esters as substrates.A mixture of L-tyrosine ethyl ester hydrochloride, the appropriate acid anhydri-des, triethylamine and dry tetrahydrofuran, was warmed for an hour in an atmosphere of nitrogen. After removing the amine salt, Ic and Id became crystalline on standing overnight in the cold.

Preparation

synthesis of L-Tyrosine Ethyl Ester Hydrochloride: Esterification of 25 g. ol L-tyrosine (0.014 mole) with ethanolic hydrogen chloride gave 24.1 g. of L-tyrosine ethyl ester hydrochloride (80%). Liberation of the ester by slurrying the hydrochloride in chloroform rollowed by the addition of chloroform saturated with ammonia, removal of the ammonium chloride by filtration and evaporation of the chloroform gave 19.4 g. of L-tyrosine ethyl ester (67%), m.p. 106-108 ° .

InChI:InChI=1/C11H15NO3/c1-2-15-11(14)10(12)7-8-3-5-9(13)6-4-8/h3-6,10,13H,2,7,12H2,1H3/p+1/t10-/m0/s1

Upstream product

• 1634-04-4 tert-butyl methyl ether 
• 60-18-4 L-tyrosine 
• 64-17-5 ethanol 

Downstream Products

• 58559-09-4 Ethyl N-(p-tosyl)tyrosinate 
• 16152-92-4 N-Benzyloxycarbonyl-L-asparaginyl-L-tyrosin-ethylester 
• 35959-85-4 N-(N,S-ditrityl-L-cysteinyl)-L-tyrosine ethyl ester 
• 13122-97-9 N-benzyloxycarbonyl-L-alanyl-L-tyrosine 
• 70935-42-1 (tert-butoxycarbonyl)glycyl-L-tyrosine ethyl ester 
• 182485-33-2 (-)-(S)-N-(6-Oxocyclohex-1-enyl)tyrosine ethyl ester 
• 168846-66-0 (S)-2--3-(4-hydroxyphenyl)propanoate d'ethyle 
• 3249-01-2 N-(N-benzyloxycarbonyl-glycyl)-L-tyrosine ethyl ester 
• 3392-15-2 N-benzyloxycarbonyl-L-phenylalanyl-L-tyrosine ethyl ester 
• 16152-80-0 benzyloxycarbonyl-S-benzylcysteinyl-tyrosine ethyl ester 
• 76658-39-4 ethyl tert-butoxycarbonyl-L-alanyl-L-tyrosinate 
• 16679-94-0 N-[(phenylmethoxy)carbonyl]-L-tyrosine 
• 79598-35-9 benzyloxycarbonylvalyltyrosine ethyl ester 
• 153152-86-4 Ethyl (2S,2'E,4'E,6'R)-2-(4,6-dimethyldodeca-2,4-dienoylamido)-3-(4-hydroxyphenyl)propanoate 

Relevant articles and documents

Peripheral Selective Oxadiazolylphenyl Alanine Derivatives as Tryptophan Hydroxylase 1 Inhibitors for Obesity and Fatty Liver Disease

Tryptophan hydroxylase 1 (TPH1) has been recently suggested as a promising therapeutic target for treating obesity and fatty liver disease. A new series of 1,2,4-oxadiazolylphenyl alanine derivatives were identified as TPH1 inhibitors. Among them, compound 23a was the most active in vitro, with an IC50 (half-maximal inhibitory concentration) value of 42 nM, showed good liver microsomal stability, and showed no significant inhibition of CYP and hERG. Compound 23a inhibited TPH1 in the peripheral tissue with limited BBB penetration. In high-fat diet-fed mice, 23a reduced body weight gain, body fat, and hepatic lipid accumulation. Also, 23a improved glucose intolerance and energy expenditure. Taken together, compound 23a shows promise as a therapeutic agent for the treatment of obesity and fatty liver diseases.

NOVEL TRYPTOPHAN HYDROXYLASE INHIBITOR AND PHARMACEUTICAL COMPOSITION INCLUDING SAME

The present invention relates to a novel tryptophan hydroxylase inhibitor and a pharmaceutical composition including same, wherein the novel tryptophan hydroxylase inhibitor has an excellent inhibitory effect on TPH1, and thus can be usefully used for the prevention or treatment of disorders, such as metabolic disorders, cancer, digestive or cardiovascular system disorders, related to TPH1 activity. In particular, the novel tryptophan hydroxylase inhibitor has an excellent treatment effect on inflammatory bowel disorders, and thus can be usefully used for the treatment of inflammatory bowel disorder.

Synthesis of a series of amino acid derived ionic liquids and tertiary amines: Green chemistry metrics including microbial toxicity and preliminary biodegradation data analysis

A series of l-phenylalanine ionic liquids (ILs), l-tyrosine ILs, tertiary amino analogues and proposed transformation products (PTPs) have been synthesised. Antimicrobial toxicity data, as part of the green chemistry metrics evaluation and to supplement preliminary biodegradation studies, was determined for ILs, tertiary amino analogues and PTPs. Good to very good overall yields (76 to 87%) for the synthesis of 6 ILs from l-phenylalanine were achieved. A C2-symmetric IL was prepared from TMS-imidazole in a one-pot two-step method in excellent yield (91%). Synthesis of the l-tyrosine IL derivatives utilised a simple protection group strategy by using an extra equivalent of the bromoacetyl bromide reagent. Improvements in the synthesis of the α-bromoamide alkylating reagent from l-phenylalanine were achieved, directed by green chemistry metric analysis. A solvent switch from dichloromethane to THF is described, however the yield was 15% lower. Antimicrobial activity testing of l-phenylalanine ILs, l-tyrosine ILs, tertiary amino analogues and PTPs, against 8 bacteria and 12 fungi strains, showed that no compound had a high antimicrobial activity, apart from an l-proline analogue. In this exceptional case, the highest toxicity (IC95 = 125 and 250 μM) was observed towards the two Gram positive strains Staphylococcus aureus and Staphylococcus epidermidis respectively. High antimicrobial activity was not found for the other bacteria or fungi strains screened. The limitations of the antimicrobial activity study is discussed in relation to SAR studies. Preliminary analysis of biodegradation data (Closed Bottle Test, OECD 301D) is presented. The pyridinium IL derivative is the preferred green IL of the series based on synthesis, toxicity and biodegradation considerations. This work is a joint study with Kümmerer and co-workers and the PTPs were selected as target compounds based on concurrent biodegradation studies by the Kümmerer group. For the comprehensive biodegradation and transformation product analysis see the accompanying paper.