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

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

1. Used in Pharmaceutical and Organic Synthesis:
Ethyl L-tyrosinate hydrochloride is used as a medical and organic intermediate due to its ability to participate in various chemical reactions and synthesis processes. Its unique structure allows it to be a versatile building block in the development of new pharmaceutical compounds and organic molecules.
2. Used as an Amino Protective Agent:
Ethyl L-tyrosinate hydrochloride serves as an important amino protective agent, which is crucial in the synthesis of complex organic molecules. Protecting groups are essential in organic chemistry to prevent unwanted reactions at the amino group, ensuring the desired product is obtained.
3. Application in Introducing t-Boc Protect Gene:
Ethyl L-tyrosinate hydrochloride is also utilized to introduce the t-Boc (tert-butyloxycarbonyl) protect gene in molecular biology. The t-Boc group is a widely used protecting group for amino groups, and its introduction is vital for the synthesis of peptides and other biomolecules.
4. Used in Synthesis of Poly(L-tyrosine) and Poly(L-glutamic acid):
Ethyl L-tyrosinate hydrochloride is employed in the synthesis of poly(L-tyrosine) and poly(L-glutamic acid) using L-tyrosine ethyl ester hydrochloride and L-glutamic acid diethyl ester hydrochloride as 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.
5. Application in Chemical Reactions:
In a typical chemical reaction, a mixture of L-tyrosine ethyl ester hydrochloride, the appropriate acid anhydrides, triethylamine, and dry tetrahydrofuran is warmed for an hour in an atmosphere of nitrogen. After removing the amine salt, the desired products (Ic and Id) become crystalline upon standing overnight in the cold, showcasing the compound's utility in chemical synthesis processes.

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

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

Downstream Products

• 101918-81-4 N,N'-oxalyl-di-L-tyrosine diethyl ester 
• 124103-83-9 N-(penta-O-acetyl-D-gluconoyl)-L-tyrosine ethyl ester 
• 908574-17-4 N-(3-iodo-propionyl)-L-tyrosine ethyl ester 
• 132562-61-9 N-((S)-2-amino-butyryl)-L-tyrosine ethyl ester; hydrochloride 
• 150571-00-9 ethyl N-benzyloxycarbonyl-D-alanyl-L-tyrosinate 
• 79598-35-9 benzyloxycarbonylvalyltyrosine ethyl ester 
• 21820-51-9 O-phosphono-L-tyrosine 
• 60-18-4 L-tyrosine 
• 32771-70-3 N-(4-nitro-benzoyl)-L-tyrosine ethyl ester 
• 16679-94-0 N-[(phenylmethoxy)carbonyl]-L-tyrosine 
• 16679-93-9 N,O-bis-benzyloxycarbonyl-L-tyrosine ethyl ester 
• 40829-21-8 (S)-2-amino-N-benzyl-3-(4-hydroxyphenyl)propanamide 
• 1071694-87-5 N-[N-(toluene-4-sulfonyl)-L-γ-glutamyl]-L-tyrosine ethyl ester 
• 3249-01-2 N-(N-benzyloxycarbonyl-glycyl)-L-tyrosine ethyl ester 

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.

Method for preparing Fmoc-Tyr (tBu)-OH

The invention relates to a method for preparing FmocTyr (tBu)-OH, and belongs to the technical field of medical intermediate chemical engineering. The technical problem to be solved by the invention is to provide a method for preparing Fmoc-Tyr (tBu)-OH with good safety. The method comprises the following steps: a, mixing an Fmoc-Tyr-OR solid, tert-butyl acetate, perchloric acid and tert-butyl alcohol to react, adjusting the pH value to 5-6, separating out a solid, filtering, washing and drying to obtain an Fmoc-Tyr (tBu)-OR solid, wherein R is a C1-C4 alkyl; and b, carrying out hydrolysis onthe Fmoc-Tyr (tBu)-OR solid to obtain an Fmoc-Tyr (tBu)-OH product. The method is improved on the basis of the existing synthetic route, isobutene is not added when tert-butyl is introduced, the operation is simple and controllable, the safety is good, the cost is low, the production steps can be effectively shortened, the production efficiency and the yield are improved, and the method is suitable for modern industrial production.

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.

Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids

The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs.

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.

Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C

A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.

CYCLIC AMINO ACID DERIVATIVES

Disclosed are the compounds of formula I STR1 wherein R represents hydrogen, lower alkyl, carbocyclic or heterocyclic aryl-lower alkyl or cycloalkyl-lower alkyl; R 1 represents hydrogen, lower alkyl, cycloalkyl, carbocyclic aryl or heterocyclic aryl, or biaryl; R 3 represents hydrogen or acyl; R 4 represents hydrogen, lower alkyl, carbocyclic or heterocyclic aryl, carbocyclic or heterocyclic aryl-lower alkyl, cycloalkyl, cycloalkyl-lower alkyl, biaryl or biaryl-lower alkyl; R 5 represents hydrogen or lower alkyl; or R 4 and R 5 together with the carbon atom to which they are attached represent cycloalkylidene or benzo-fused cycloalkylidene; A together with the carbon atom to which it is attached represents 3 to 10 membered cycloalkylidene or 5 to 10 membered cycloalkenylidene radical which may be substituted by lower alkyl or aryl-lower alkyl or may be fused to a saturated or unsaturated carbocyclic 5-7-membered ring; or A together with the carbon to which it is attached represents 5 or 6 membered oxacycloalkylidene, thiacycloalkylidene or azacycloalkylidene optionally substituted by lower alkyl or aryl-lower alkyl; or A together with the carbon atom to which it is attached represents 2,2-norbornylidene; m is 0, 1, 2 or 3; and COOR 2 represents carboxyl or carboxyl derivatized in form of a pharmaceutically acceptable ester, disulfide derivatives derived from said compounds wherein R 3 is hydrogen; and pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising said compounds; methods for preparation of said compounds; intermediates; and methods of treating disorders in mammals which are responsive to ACE and NEP inhibition by administration of said compounds to mammals in need of such treatment.

9. Les β-cetonitriles groupes protecteurs de la fonction amine. Preparation d'amino-alcools

β-Ketonitrile-Derived Protecting Groups of the Amino Function.Synthesis of Amino Alcohols.The amino group of natural L-amino acid esters is protected by condensation with 2-oxocyclopentanenitrile (1) or 2-formyl-2-phenylacetonitrile (10).Only the ester group of the formed cyanoenamino esters 2 and 11 reacts with nucleophilic reagents such as organometallics (RMgX, RLi), borohydrides, or metal amides, whereas the cyanoenamino group is unchanged (Schemes 1 and 2).Cyanoenamino alcohols obtained by reduction of cyanoenamino esters 2 are hydrolyzed under acidic conditions to amino alcohols with retention of the configuration of the starting amino acid.This sequence of reactions allows to prepare derivatives of L-tyrosinol from (-)-L-tyrosine (see, e.g., Scheme 4).Cyanoenamino esters 11 are readily methylated at the N-atom to give N-methylated cyanoenamino esters (Scheme 3).This property is exploited on the way of multistep procedure to obtain N-methylated amino alcohols homologous to natural (-)-(1R,2S)-ephedrine.