Methyl L-tyrosinate

Base Information

• Chemical Name: Methyl L-tyrosinate
• CAS No.: 1080-06-4
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 2922509090
• European Community (EC) Number: 214-095-3
• UNII: WR2XY2Y23P
• DSSTox Substance ID: DTXSID40148354
• Nikkaji Number: J5.190J
• Wikidata: Q27102267
• Metabolomics Workbench ID: 50819
• ChEMBL ID: CHEMBL300797
• Mol file: 1080-06-4.mol

Synonyms:tyrosine methyl ester;tyrosine methyl ester hydrochloride, (D)-isomer;tyrosine methyl ester hydrochloride, (L)-isomer

Chemical Property of Methyl L-tyrosinate

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 8.89E-05mmHg at 25°C
• Melting Point: 134-136 °C(lit.)
• Refractive Index: 1.5150 (estimate)
• Boiling Point: 330 °C at 760 mmHg
• PKA: pKa 7.04±0.02(H2O t=25.0±0.1 I=0.1(NaCl) N2atmosphere) (Uncertain);9.73±0.03(H2O t=25.0±0.1 I=0.1(NaCl) N2atmosphere) (Uncertain)
• Flash Point: 153.4 °C
• PSA: 72.55000
• Density: 1.21 g/cm³
• LogP: 1.13530
• Storage Temp.: −20°C
• Solubility.: Chloroform, Ethyl Acetate, Methanol
• Water Solubility.: Soluble in water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 188

Purity/Quality:

99% ^*data from raw suppliers

Methyl-L-tyrosinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=C(C=C1)O)N
• Isomeric SMILES: COC(=O)[C@H](CC1=CC=C(C=C1)O)N
• Uses: L-Tyrosine-induced antinociception is mediated by central .delta.-opioid receptors and by the bulbo-spinal noradrenergic system. L-Tyrosine methyl ester is used as a dehydroepiandrosterone as a sulfate acceptor

Technology Process of Methyl L-tyrosinate

There total 36 articles about Methyl L-tyrosinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → L-Tyr-OMe (1080-06-4)

Guidance literature:

With thionyl chloride; 1.) room temperature, 2 h, 2.) reflux, 0.5 h;

DOI:10.1021/jo961447m

Reference yield: 100.0%

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + acetyl chloride (75-36-5) → L-Tyr-OMe (1080-06-4)

Guidance literature:

In methanol; for 5h; Heating;

DOI:10.1021/ja074392m

Reference yield: 97.0%

L-tyrosine methyl ester HCl (3417-91-2) → L-Tyr-OMe (1080-06-4)

Guidance literature:

With potassium hydrogencarbonate; In ethyl acetate; for 4h;

DOI:10.1002/ejoc.200300366

upstream raw materials:

methanol

L-tyrosine

3-(4-Hydroxy-phenyl)-2-((E)-3-oxo-propenylamino)-propionic acid methyl ester

3-(4-Hydroxy-phenyl)-2-((E)-2-methyl-3-oxo-propenylamino)-propionic acid methyl ester

Downstream raw materials:

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

L-tyrosine

(S)-methyl 2-(dodecanamido)-3-(4-hydroxyphenyl)propanoate

3-(4-Hydroxy-phenyl)-2-[2-(1H-indol-3-yl)-2-oxo-acetylamino]-propionic acid methyl ester

Refernces

• 1、 Perrone, Maria L.,Salvadeo, Elena,Lo Presti, Eliana,Pasotti, Luca,Monzani, Enrico,Santagostini, Laura,Casella, Luigi. "A dinuclear biomimetic Cu complex derived from l-histidine: synthesis and stereoselective oxidations". . p. 4018 - 4029. Retrieved 2017.
• 2、 Tiwari, Priyanka,Basu, Anindya,Sahu, Sonu,Gound, Sadhna,Christman, Ryann M.,Tiwari, Amit K.,Trivedi, Piyush,DuttKonar, Anita. "An auxin-tyrosine derivative based biocompatible supergelator: A template for fabrication of nanoparticles for sustained release of model drugs". . p. 4915 - 4922. Retrieved 2018.
• 3、 Jackson,A.E.,Johnstone,R.A.W.. "-". . p. 685 - 687. Retrieved 1976.
• 4、 Zagotto,Supino,Favini,Moro,Palumbo. "New 1,4-anthracene-9,10-dione derivatives as potential anticancer agents". . p. 1 - 5. Retrieved 2000.
• 5、 Watanabe, Ken-ichi,Yamada, Yoichi,Goto, Katsuhisa. "New Type of Aldol Condensations Catalyzed by Metal(II) Complexes of α-Amino Acid Esters and that with Cyclodextrin System". . p. 1401 - 1406. Retrieved 1985.
• 6、 Knudsen, Kristian Rahbek,Holden, John,Ley, Steven V.,Ladlow, Mark. "Optimisation of conditions for O-benzyl and N-benzyloxycarbonyl protecting group removal using an automated flow hydrogenator". . p. 535 - 538. Retrieved 2007.
• 7、 Cormanich, Rodrigo A.,Ducati, Lucas C.,Tormena, Cláudio F.,Rittner, Roberto. "Phenylalanine and tyrosine methyl ester intramolecular interactions and conformational analysis by 1H NMR and infrared spectroscopies and theoretical calculations". . p. 482 - 489. Retrieved 2014.
• 8、 Drescher, Christian,Brückner, Reinhard. "Stereostructure Clarifying Total Synthesis of the (Polyenoyl)tetramic Acid Militarinone B. A Highly Acid-Labile N-Protecting Group for Amides ?". . p. 6194 - 6199. Retrieved 2021.
• 9、 Wang, Jianqiang,Zhang, Wenqi,Gu, Changqing,Zhang, Wenpei,Zhou, Man,Wang, Zhiwei,Guo, Cheng,Sun, Linbing. "Step-Up Synthesis of Periodic Mesoporous Organosilicas with a Tyrosine Framework and Performance in Horseradish Peroxidase Immobilization". . p. 3162 - 3171. Retrieved 2017.
• 10、 Botta, Bruno,D'Acquarica, Ilaria,Nevola, Laura,Sacco, Fabiola,Lopez, Zara Valbuena,Zappia, Giovanni,Fraschetti, Caterina,Speranza, Maurizio,Tafi, Andrea,Caporuscio, Fabiana,Letzel, Matthias C.,Mattay, Jochen. "Bis(diamido)-bridged basket resorcin[4]arenes as enantioselective receptors for amino acids and amines". . p. 5995 - 6002. Retrieved 2007.