2-Amino-3-(4-hydroxyphenyl)-propanoic acid

Base Information

• Chemical Name: 2-Amino-3-(4-hydroxyphenyl)-propanoic acid
• CAS No.: 556-02-5
• Molecular Formula: C9H11NO3
• Molecular Weight: 181.191
• Hs Code.: H11NO3 MOL WT. 181.19
• Mol file: 556-02-5.mol

Synonyms:D-tyrosine zwitterion;2-amino-3-(4-hydroxyphenyl)-propanoic acid;CHEBI:58570;(2R)-2-ammonio-3-(4-hydroxyphenyl)propanoate

Chemical Property of 2-Amino-3-(4-hydroxyphenyl)-propanoic acid

Chemical Property:

• Appearance/Colour: white to off-white powder
• Vapor Pressure: 1.27E-06mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 11.2 ° (C=5, 1mol/L HCl)
• Boiling Point: 385.2 °C at 760 mmHg
• PKA: 2.25±0.10(Predicted)
• Flash Point: 186.7 °C
• PSA: 83.55000
• Density: 1.333 g/cm³
• LogP: 1.04690
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 181.07389321
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

D-Tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)[O-])[NH3+])O
• Isomeric SMILES: C1=CC(=CC=C1C[C@H](C(=O)[O-])[NH3+])O
• Description: D-tyrosine is the D-form amino acid of tyrosine. It is a non-essential amino acid. In animals, it can be de novo synthesized from phenylalanine. It is also the precursor of epinephrine, thyroid, hormones and melanin. Specially, study has shown that it can be taken s a chiral precusor to potent inhibitors of human Nonpancreatic secretory phospholipase A 2(IIa) with strong anti-inflammatory activity. It can also be used as a starting material for the preparation of anisomycin.
• Uses: D-Tyrosine, the stereoisomer to L-Tyrosine (T899975), is an amino acid used in various organic syntheses for antibiotics. It is used in the synthesis of (-)-anisomycin, as well as BATSI (boronic acid transition state inhibitors) which act on β-lactamases. It has also been studied as an inhibitor of microbial growth on surfaces, reducing microbial attachment to hydrophillic glass and hydrophobic po lypropylene surfaces. D-Tyrosine is synthesized from phenylalanine. It is also the precursor of epinephrine, thyroid hormones, and melanin.

Technology Process of 2-Amino-3-(4-hydroxyphenyl)-propanoic acid

There total 143 articles about 2-Amino-3-(4-hydroxyphenyl)-propanoic acid 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: 94.0%

4-hydroxyphenylpiruvic acid (156-39-8) → 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid (6482-98-0,23508-35-2,89919-57-3,306-23-0) + ?Tyr (556-02-5,556-03-6,34537-57-0,55520-40-6,96946-98-4,60-18-4,18875-48-4,25619-78-7,30704-25-7)

Guidance literature:

With [Ir(III)Cp*(bpy)(OH₂)](SO₄); ammonium formate; In water; at 80 ℃; for 24h; pH=5.0;

DOI:10.1021/ja031633r

Reference yield:

N-((Ξ)-benzylidene)-L-tyrosine ; sodium-salt → benzaldehyde (100-52-7) + ?Tyr (556-02-5,556-03-6,34537-57-0,55520-40-6,96946-98-4,60-18-4,18875-48-4,25619-78-7,30704-25-7)

Guidance literature:

Reference yield:

tiglicamide C (1207162-72-8) → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-methionine sulfoxide (3226-65-1,86631-49-4,779988-65-7) + D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + tyrosine (556-02-5,18875-48-4,25619-78-7,30704-25-7)

Guidance literature:

With hydrogenchloride; water; at 116 ℃; for 24h;

DOI:10.1016/j.phytochem.2009.09.010

upstream raw materials:

2-acetylamino-2-(4-methoxybenzyl)malonic acid diethyl ester

2-benzoylamino-3-(4-hydroxy-phenyl)-acrylic acid

(p-aminophenyl)alanine

[2-hydroxyimino-3-(4-hydroxyphenyl)]propionic acid

Downstream raw materials:

N-formyl-DL-tyrosine

tyrosine isopentyl ester

N-carbamoyltyrosine

5-(4-hydroxy-benzyl)-imidazolidine-2,4-dione

Refernces

• 1、 Jiang, Hong,Yang, Kuiwei,Zhao, Xiangxiang,Zhang, Wenqiang,Liu, Yan,Jiang, Jianwen,Cui, Yong. "Highly Stable Zr(IV)-Based Metal-Organic Frameworks for Chiral Separation in Reversed-Phase Liquid Chromatography". supporting information. p. 390 - 398. Retrieved 2021/01/13.
• 2、 Nguyen, Dat P.,Sladek, Rudolph N.,Do, Loi H.. "Scope and limitations of reductive amination catalyzed by half-sandwich iridium complexes under mild reaction conditions". supporting information. . Retrieved 2020/07/15.