D-4-Hydroxyphenylglycine

Base Information

• Chemical Name: D-4-Hydroxyphenylglycine
• CAS No.: 22818-40-2
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.164
• Hs Code.: 2922.49
• European Community (EC) Number: 245-247-7
• UNII: PCM9OIX717
• DSSTox Substance ID: DTXSID401014840
• Wikidata: Q27095129
• Metabolomics Workbench ID: 50225
• Mol file: 22818-40-2.mol

Synonyms:(R,S)-3HPG;4-hydroxyphenylglycine;4-hydroxyphenylglycine hydrobromide, (+-)-isomer;4-hydroxyphenylglycine hydrochloride, (R)-isomer;4-hydroxyphenylglycine perchlorate, (+-)-isomer;4-hydroxyphenylglycine, (+-)-isomer;4-hydroxyphenylglycine, (R)-isomer;4-hydroxyphenylglycine, (S)-isomer;4-hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomer;4-hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomer;4-hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomer;4-hydroxyphenylglycine, 4-methylbenzenesulfonate, (S)-isomer;4-hydroxyphenylglycine, monosodium salt;4-hydroxyphenylglycine, monosodium salt, (R)-isomer;D-p-hydroxyphenylglycine;L-4-hydroxyphenylglycine;oxfenicine;p-hydroxyphenylglycine;UK 25842;UK-25842

Chemical Property of D-4-Hydroxyphenylglycine

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 0.000272mmHg at 25°C
• Melting Point: 240 °C (dec.)(lit.)
• Refractive Index: -158 ° (C=1, 1mol/L HCl)
• Boiling Point: 365.8 °C at 760 mmHg
• PKA: 2.15±0.10(Predicted)
• Flash Point: 175 °C
• PSA: 83.55000
• Density: 1.396 g/cm³
• LogP: 1.17690
• Storage Temp.: Store below +30°C.
• Solubility.: 5g/l
• Water Solubility.: 5 g/L (20 ºC)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 167.058243149
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy-D-(-)-2-phenylglycine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(=O)O)N)O
• Isomeric SMILES: C1=CC(=CC=C1[C@H](C(=O)O)N)O
• Uses: 4-Hydroxy-D-(-)-2-phenylglycine is an compound used mainly for the synthetic preparation of β-lactam antibiotics. 4-Hydroxy-D-(-)-2-phenylglycine (Cefadroxil EP Impurity A(Amoxicillin EP Impurity A)) is an compound used mainly for the synthetic preparation of β-lactam antibiotics.

Technology Process of D-4-Hydroxyphenylglycine

There total 35 articles about D-4-Hydroxyphenylglycine 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: 97.8%

potassium cyanide + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → D-4-hydroxyphenylglycine (22818-40-2)

Guidance literature:

With nitrilase AY₄₈₇₅₃₃; In aq. acetate buffer; at 20 ℃; for 1h; pH=8; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/cctc.201801254

Reference yield: 94.0%

5-(4-hydroxy-phenyl)-imidazolidine-2,4-dione (2420-17-9,54832-24-5) → D-4-hydroxyphenylglycine (22818-40-2)

Guidance literature:

In water; at 30 ℃; for 48h; 0.1 M potassium phosphate buffer (pH = 8.0); cells of Pseudomonas sp. AJ-11220 (bacterioal strain H-231); ivestigate steric configuration of the product; other time;

Reference yield: 93.0%

(R)-N-phenylacetyl-D-(4-hydroxyphenyl)-glycine (54582-01-3,84709-13-7) → D-4-hydroxyphenylglycine (22818-40-2)

Guidance literature:

With hydrogenchloride; water; at 50 ℃; for 10h;

DOI:10.1002/adsc.200800203

upstream raw materials:

(S)-2-Amino-3-{[(R)-carboxy-(4-hydroxy-phenyl)-methyl]-amino}-propionic acid

(R)-ethyl 2-amino-2-(4-hydroxyphenyl)acetate

5-[2-(methylthio)ethyl]imidazolidine-2,4-dione

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

Refernces

• 1、 Bhattacharya,Araullo-Mcadams,Meier. "Crystallization induced asymmetric transformation: Synthesis of D-p-hydroxyphenylglycine". . p. 2449 - 2459. Retrieved 1994.
• 2、 Yamada,Tobiki,Tanno,Suzuki,Jimpo,Ueda,Nakagome. "D-2-AMINO-2-(4-HYDROXYPHENYL)ACETAMIDO.". . p. 3333 - 3334. Retrieved 1984.
• 3、 -. "Clean production method of L-p-hydroxyphenylglycine". Paragraph 0027-0034. . Retrieved 2022/01/24.
• 4、 Akhtar, M. Kalim,Campopiano, Dominic J.,De Cesare, Silvia,Loake, Gary J.,Marles-Wright, Jon,Serpico, Annabel. "D-Phenylglycine aminotransferase (d-PhgAT)-substrate scope and structural insights of a stereo-inverting biocatalyst used in the preparation of aromatic amino acids". . p. 6533 - 6543. Retrieved 2020/11/13.