4-Hydroxy-D-phenylglycine - ≥99% , CAS No.22818-40-2

CAS: 22818-40-2 Cat. No.: H111804 Molecular Weight: 167.16 Beilstein Registry Number: 2210998 EC Number: 245-247-7

GRADE & PURITY ≥99%

Synonyms

(2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetate;(R)-2-Amino-2-(4-hydroxyphenyl)acetic Acid | (R)--Amino-4-hydroxybenzeneacetic acid | Benzeneacetic acid, .alpha.-amino-4-hydroxy-, (.alpha.R)- | Benzeneacetic acid, alpha-amino-4-hydroxy-, (alphaR)- | D-alpha-(

Storage

Room temperature

Shipped In

Normal

Overview

Application：

(-)-4-Hydroxy-D-phenylglycine is used as an organic chemical synthesis intermediate.

Specifications

Synonyms

(2R)-2-azaniumyl-2-(4-hydroxyphenyl)acetate;(R)-2-Amino-2-(4-hydroxyphenyl)acetic Acid | (R)--Amino-4-hydroxybenzeneacetic acid | Benzeneacetic acid, .alpha.-amino-4-hydroxy-, (.alpha.R)- | Benzeneacetic acid, alpha-amino-4-hydroxy-, (alphaR)- | D-alpha-(

Specifications & Purity

≥99%

Storage

Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488186573
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488186573
• Canonical Smiles: C1=CC(=CC=C1C(C(=O)O)N)O
• IUPAC Name: (2R)-2-amino-2-(4-hydroxyphenyl)acetic acid
• InChIKey: LJCWONGJFPCTTL-SSDOTTSWSA-N
• INCHI: 1S/C8H9NO3/c9-7(8(11)12)5-1-3-6(10)4-2-5/h1-4,7,10H,9H2,(H,11,12)/t7-/m1/s1
• Isomeric SMILES: C1=CC(=CC=C1[C@H](C(=O)O)N)O
• WGK Germany: 3
• Molecular Weight: 167.16
• Beilstein: 2210998
• Reaxy-Rn: 513130
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=513130&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 D-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: D-alpha-amino acids
• Alternative Parents: Aralkylamines 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Amino acids Monocarboxylic acids and derivatives Carboxylic acids Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: D-alpha-amino acid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Amine - Hydrocarbon derivative - Primary amine - Organic oxide - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Primary aliphatic amine - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
• External Descriptors: 4-hydroxyphenylglycine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water (5 g/L at 20°C) and 1 mol/l HCl.
• Specific Rotation[α]: -158 ° (C=1, 1mol/L HCl)
• Melt Point(°C): 204°C
• Molecular Weight: 167.160 g/mol
• XLogP3: -2.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 167.058 Da
• Monoisotopic Mass: 167.058 Da
• Topological Polar Surface Area: 83.600 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 164.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xin Pan, Anni Li, Zhiyi Peng, Xiaoqi Ji, Jianlin Chu, Bingfang He.  (2020)  Efficient synthesis of β-lactam antibiotics with in situ product removal by a newly isolated penicillin G acylase.  BIOORGANIC CHEMISTRY,      [PMID:32213361] [10.1016/j.bioorg.2020.103765]

2. Jiajie Ye, Anni Li, Tianshu Chu, Xin Pan, Bingfang He.  (2019)  Poly-lysine supported cross-linked enzyme aggregates of penicillin G acylase and its application in synthesis of β-lactam antibiotics.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:31381925] [10.1016/j.ijbiomac.2019.08.021]

3. Pan Xin, Wang Li, Ye Jiajie, Qin Song, He Bingfang.  (2018)  Efficient synthesis of β-lactam antibiotics with very low product hydrolysis by a mutant Providencia rettgeri penicillin G acylase.  APPLIED MICROBIOLOGY AND BIOTECHNOLOGY,  102  (4): (1749-1758).  [PMID:29306966] [10.1007/s00253-017-8692-8]