Description

D-(-)-4-Hydroxyphenylglycine (CAS No. 22818-40-2) is a high-purity chiral amino acid derivative widely utilized in pharmaceutical synthesis and biochemical research. With the molecular formula C₈H₉NO₃, this compound serves as a critical intermediate in the production of beta-lactam antibiotics, including amoxicillin and cefadroxil. Its (R)-configuration ensures enantioselective efficacy in drug formulations. Our product is rigorously tested to meet pharmacopeial standards (EP/BP/USP) and is available in ≥98% purity, making it ideal for API manufacturing, impurity reference standards, and asymmetric synthesis. Packaged under inert conditions to ensure stability, it is supplied as a white to off-white crystalline powder with exceptional lot-to-lot consistency.

Properties

• CAS Number: 22818-40-2
• Complexity: 164
• IUPAC Name: (2R)-2-amino-2-(4-hydroxyphenyl)acetic acid
• InChI: 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
• InChI Key: LJCWONGJFPCTTL-SSDOTTSWSA-N
• Exact Mass: 167.058243149
• Molecular Formula: C8H9NO3
• Molecular Weight: 167.16
• SMILES: C1=CC(=CC=C1[C@H](C(=O)O)N)O
• Topological: 83.6
• Monoisotopic Mass: 167.058243149
• Synonyms: 22818-40-2, D-4-Hydroxyphenylglycine, 4-Hydroxy-D-phenylglycine, D-(-)-4-Hydroxyphenylglycine, D-N-(4-Hydroxyphenyl)glycine, (R)-alpha-Amino-4-hydroxybenzeneacetic acid, D-P-HYDROXYPHENYLGLYCINE, 4-Hydroxyphenylglycine, D-(-)-, PCM9OIX717, P-hydroxy-(R)-phenylglycine, D-(-)-p-Hydroxyphenylglycine, (2R)-amino(4-hydroxyphenyl)acetic acid, (R)-2-(4-HYDROXYPHENYL)GLYCINE, CHEBI:15695, EINECS 245-247-7, (R)-(4-HYDROXYPHENYL)GLYCINE, D-(-)-amino(4-hydroxyphenyl)acetic acid, D-2-amino-2-(p-hydroxyphenyl)acetic acid, D-(-)-2-(P-HYDROXYPHENYL)GLYCINE, (R)-Ethyl 2-amino-2-(4-hydroxyphenyl)acetate, EC 245-247-7, DTXSID401014840, Benzeneacetic acid, alpha-amino-4-hydroxy-, (alphaR)-, D-.ALPHA.-P-HYDROXYPHENYLGLYCINE, Benzeneacetic acid, .alpha.-amino-4-hydroxy-, (.alpha.R)-, CEFPROZIL IMPURITY A [EP IMPURITY], CEFADROXIL IMPURITY A [EP IMPURITY], AMOXICILLIN IMPURITY I [EP IMPURITY], GLYCINE, 2-(P-HYDROXYPHENYL)-, D-, (alphaR)-alpha-Amino-4-hydroxybenzeneacetic acid, D-(-)-.ALPHA.-(4-HYDROXYPHENYL)GLYCINE, D-.ALPHA.-AMINO-4-HYDROXYPHENYLACETIC ACID, AMOXICILLIN TRIHYDRATE IMPURITY I [EP IMPURITY], CEFADROXIL MONOHYDRATE IMPURITY A [EP IMPURITY], CEFPROZIL MONOHYDRATE IMPURITY A [EP IMPURITY], D-(-)-.ALPHA.-AMINO-4-HYDROXYPHENYLACETIC ACID, (.ALPHA.R)-.ALPHA.-AMINO-4-HYDROXYBENZENEACETIC ACID, CEFPROZIL IMPURITY A (EP IMPURITY), CEFADROXIL IMPURITY A (EP IMPURITY), AMOXICILLIN IMPURITY I (EP IMPURITY), AMOXICILLIN TRIHYDRATE IMPURITY I (EP IMPURITY), CEFADROXIL MONOHYDRATE IMPURITY A (EP IMPURITY), CEFPROZIL MONOHYDRATE IMPURITY A (EP IMPURITY), DTXCID401473163, D-ALPHA-P-HYDROXYPHENYLGLYCINE, D-(-)-ALPHA-(4-HYDROXYPHENYL)GLYCINE, D-ALPHA-AMINO-4-HYDROXYPHENYLACETIC ACID, D-(-)-ALPHA-AMINO-4-HYDROXYPHENYLACETIC ACID, 245-247-7, (2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetate, D(-)-4-Hydroxyphenylglycine, H-D-PHG(4-OH)-OH, (2R)-2-amino-2-(4-hydroxyphenyl)acetic acid, (R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETIC ACID, Benzeneacetic acid, a-amino-4-hydroxy-, (aR)-, p-hydroxy-D-phenylglycine, MFCD00004262, 4-HYDROXY-D-(-)-2-PHENYLGLYCINE, (2R)-amino(4-hydroxyphenyl)ethanoic acid, L-P-HYDROXYPHENYGLYCINE, UNII-PCM9OIX717, Cefprozil impurity A, d-4-hydroxyphenylglicyne, D-4-Hydroxyphenylglycine?, Epitope ID:117718, p-Hydroxyphenyl glycine HCl, SCHEMBL124861, D-?-(4-hydroxyphenyl)glycine, D-alpha-(4-hydroxyphenyl)glycine, (R)-(4-Hydroxyphenyl)glycine; (R)-2-(4-Hydroxyphenyl)glycine; 4-Hydroxy-D-phenylglycine; D-(-)-2-(4-Hydroxyphenyl)glycine; D-(-)-2-(p-Hydroxyphenyl)glycine, D-4-Hydroxyphenylglycine (Standard), 4-Hydroxy-D-phenylglycine, >=98%, D-(-)-2-(4-Hydroxyphenyl)glycine, HY-34588R, SBB058359, AKOS006281607, AKOS015924172, AC-1085, DB04308, FH01618, (R)–Amino-4-hydroxybenzeneacetic acid, NCGC00164509-02, AS-12542, HY-34588, (|AR)-|A-Amino-4-hydroxybenzeneacetic acid, CS-0020117, H0758, NS00005440, C03493, D71081, EN300-105272, BRD-K30373577-001-01-1, Q27095129, Z1198149764, (R)-(-)-2-AMINO-2-(4-HYDROXYPHENYL)ACETIC ACID, Cefprozil impurity A, European Pharmacopoeia (EP) Reference Standard, D-alpha-(4-Hydroxy-phenyl)glycine, European Pharmacopoeia (EP) Reference Standard

D-(-)-4-Hydroxyphenylglycine is primarily employed as a chiral building block in the synthesis of semisynthetic penicillin and cephalosporin antibiotics. It acts as a key precursor for amoxicillin and cefadroxil, enhancing their antibacterial activity. Researchers also use it as an EP-certified impurity standard for quality control in pharmaceutical production. Additionally, its role in asymmetric catalysis and peptide chemistry makes it valuable for advanced organic synthesis.

Safety and Hazards

GHS Hazard Statements

• H315 (93.9%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (93.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (91.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (93.9%)
• Eye Irrit. 2A (93.9%)
• STOT SE 3 (91.8%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.