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So, let's talk about 4-Hydroxy-D-Phenylglycine. Basically, it's a chiral aromatic amino acid that chemists mostly use as a building block in pharma manufacturing. Its structure features a hydroxyphenyl group along with a D-configured amino acid center. These bits are kinda crucial because they help keep things stereochemically controlled during synthesis, which is super important when producing certain drugs. You’ll often see it playing a role in making the side chains for semi-synthetic beta-lactam antibiotics like amoxicillin and similar meds. Of course, its exact job can differ depending on the process design, supplier specs, or regional manufacturing standards, so a little variability is to be expected.

Now, it’s not the final medicine itself—more like a core piece of the puzzle. In a well-controlled production setting, chemists usually link it up with an activated beta-lactam core and then refine everything into the active pharmaceutical ingredient. But here’s the thing—getting the purity right is a big deal. They need to test for things like optical rotation, residual solvents, moisture, and any impurities. Small differences can totally throw off downstream reactions, so paying attention to those details really matters.

When it comes to technical specs, documentation should clearly list the CAS number, testing methods, stereochemical purity, and storage instructions. Buyers should also double-check if the grade they’re getting is meant for research, industrial synthesis, or actual pharmaceutical manufacturing—because just looking at a catalog description isn't enough sometimes. That’s where good judgment and experience come into play. Some online sources talk about broad uses but don’t really explain what kind of validation or testing is needed.

All in all, 4-Hydroxy-D-Phenylglycine is pretty useful for making important antibiotic intermediates. Its real value lies in its chemical reactivity coupled with stereochemical control. That said, it’s not just interchangeable with every other phenylglycine derivative out there. Trustworthy evaluation really depends on solid analytical data, well-documented sourcing, and process-specific expertise. Honestly, human oversight still makes a big difference in making sure everything’s on point.

What Is 4-Hydroxy-D-Phenylglycine Used For?
Table of Contents [Hide]
1 4-Hydroxy-D-Phenylglycine: Identity, Formula, and 167.16 g/mol Mass
2 Its Core Role as a Chiral Intermediate in β-Lactam Antibiotic Production
3 How It Forms the Side Chain of Amoxicillin and Ampicillin
4 Industrial Conversion Routes and Stereochemical Purity Requirements
5 Pharmaceutical Applications Linked to Penicillin-Class Antibiotics
6 Quality Parameters: CAS 22818-40-2, Assay, and Impurity Control

4-Hydroxy-D-Phenylglycine: Identity, Formula, and 167.16 g/mol Mass

4-Hydroxy-D-phenylglycine is a chiral aromatic amino acid derivative. Its molecular formula is C8H9NO3, and its molar mass is 167.16 g/mol. The “D” label identifies its three-dimensional configuration, not simply a purity grade. The molecule contains a phenyl ring, a para-hydroxyl group, an amino group, and a carboxylic acid group. It is commonly described as a white or off-white crystalline solid.

Its main use is as a specialized intermediate in pharmaceutical chemistry. Researchers can incorporate its D-configured side chain into selected beta-lactam antibiotic structures. It may also support studies involving chiral synthesis, reaction development, and analytical reference work. The compound itself should not be confused with a finished medicine. That distinction matters.

Small details can affect reported results. The stated 167.16 g/mol value refers to the anhydrous molecular form. Hydrates, solvates, impurities, or different assay methods may change weighing calculations. Check the certificate of analysis. Confirm stereochemical identity with suitable methods, such as optical rotation, chromatography, or spectroscopy. I would avoid assuming that every supplier’s powder behaves identically. Particle size and moisture can influence dissolution and handling. Laboratory personnel should follow the current safety data sheet, use appropriate protective equipment, and document storage conditions carefully.

What Is 4-Hydroxy-D-Phenylglycine Used For? - 4-Hydroxy-D-Phenylglycine: Identity, Formula, and 167.16 g/mol Mass

Preferred Chemical Name 4-Hydroxy-D-phenylglycine
Common Synonyms D-4-Hydroxyphenylglycine; D-p-hydroxyphenylglycine; (R)-2-amino-2-(4-hydroxyphenyl)acetic acid
Chemical Formula C8H9NO3
Molar Mass 167.16 g/mol
Molecular Class A chiral aromatic amino acid derivative containing an amino group, a carboxylic acid group, and a para-hydroxyl group.
Stereochemical Form D configuration, also designated as the R enantiomer for the commonly used structural representation.
Functional Groups Primary amine, carboxylic acid, and phenolic hydroxyl group.
Structural Description An aminoacetic acid framework attached to a para-hydroxyphenyl ring; the hydroxyl group is positioned opposite the side-chain attachment on the benzene ring.
Primary Industrial Use Used as a chiral side-chain building block and key intermediate in the manufacture of certain semi-synthetic beta-lactam antibiotics.
Pharmaceutical Applications Provides the 4-hydroxyphenylglycyl side chain used in the synthesis of antibiotics such as amoxicillin and cefadroxil.
Role in Synthesis Supplies the stereochemically defined aromatic amino-acid moiety that is coupled to an activated beta-lactam nucleus during antibiotic production.
Chemical-Research Use Used as a reference compound, chiral intermediate, and starting material in medicinal chemistry and process-development studies.
Appearance Typically described as a crystalline solid; the exact color and physical form may vary with purity, hydration state, and processing conditions.
Storage Considerations Store in a tightly closed container in a cool, dry, well-ventilated place and protect from excessive moisture and contamination.
Handling Considerations Handle as a laboratory or chemical-processing material. Avoid generating dust and use appropriate eye, skin, and respiratory protection according to the applicable safety data sheet.
Important Distinction 4-Hydroxy-D-phenylglycine is the D enantiomer. Its stereochemistry should not be confused with the corresponding L enantiomer or with a racemic mixture.

The stated formula and molar mass correspond to the anhydrous compound, C8H9NO3, with a calculated molar mass of approximately 167.16 g/mol.

Its Core Role as a Chiral Intermediate in β-Lactam Antibiotic Production

What Is 4-Hydroxy-D-Phenylglycine Used For?

4-Hydroxy-D-phenylglycine is mainly used as a chiral intermediate in β-lactam antibiotic production. It supplies the D-configured side chain needed for making certain penicillin-class medicines, especially amoxicillin-type compounds. The molecule is not the finished antibiotic. Instead, manufacturers combine its activated derivative with a 6-aminopenicillanic acid core. This step creates the final side-chain structure.

The stereochemistry matters. Small errors matter. The D-isomer supports the required three-dimensional shape and biological activity. Industrial routes often use enzymatic conversion or resolution to improve optical purity. Higher purity can reduce unwanted isomers, reprocessing, and material loss. It can also improve batch consistency during crystallization and downstream acylation. The process is not perfectly clean, though. Solvent recovery, enzyme stability, and moisture control still require careful plant experience.

Demand for reliable β-lactam intermediates reflects continued antibiotic use. The WHO AWaRe 2022 report estimated global antibiotic consumption at 40.2 billion defined daily doses in 2019. OECD Health at a Glance 2023 reported average antibiotic consumption of about 17.7 defined daily doses per 1,000 people daily across OECD countries in 2021. These figures do not measure 4-hydroxy-D-phenylglycine directly. They do show why qualified chiral building blocks remain important. Analytical testing commonly checks assay, enantiomeric purity, water content, and residual solvents. A practical weakness remains: published supply data often combine several related intermediates, making precise market estimates difficult.

How It Forms the Side Chain of Amoxicillin and Ampicillin

What Is 4-Hydroxy-D-Phenylglycine Used For?

4-Hydroxy-D-phenylglycine is a chiral amino acid used to build the side chain of amoxicillin. Its structure contains an amino group, a carboxyl group, and a para-hydroxyl group on the aromatic ring. These functional groups give the molecule useful reaction points during pharmaceutical synthesis.

In manufacturing, the amino acid is activated or converted into a suitable acylating intermediate. It then reacts with 6-aminopenicillanic acid, commonly called 6-APA. This step attaches the hydroxyphenylglycine side chain to the penicillin nucleus. The new side chain changes the drug’s polarity, absorption behavior, and antibacterial profile. Process control matters greatly here. Small changes in stereochemical purity can affect the final product.

The connection with ampicillin needs careful clarification. Ampicillin uses a closely related side-chain precursor, D-phenylglycine, without the para-hydroxyl group. Therefore, 4-hydroxy-D-phenylglycine forms the characteristic side chain of amoxicillin, while D-phenylglycine forms the side chain of ampicillin.

Their production routes share similar acylation principles, but they are not interchangeable. This distinction is easy to miss. It also shows why analytical testing must confirm identity, configuration, and residual impurities at every major stage.

Industrial Conversion Routes and Stereochemical Purity Requirements

What Is 4-Hydroxy-D-Phenylglycine Used For?

4-Hydroxy-D-phenylglycine is mainly a chiral side-chain intermediate for semisynthetic beta-lactam antibiotics. Its para-hydroxyphenyl structure supports coupling with suitable beta-lactam nuclei during active pharmaceutical ingredient production. Demand remains linked to anti-infective manufacturing. The IQVIA Institute’s Global Use of Medicines 2024 report projects global medicine spending will reach about US$2.3 trillion by 2028. That figure does not measure this intermediate directly. It does show the scale of pharmaceutical supply planning.

Industrial conversion commonly uses asymmetric synthesis, enzymatic resolution, or biocatalytic conversion of a racemic precursor. Enzyme-based routes can reduce unwanted stereoisomers and operate under milder conditions. Process teams still monitor temperature, pH, substrate loading, and reaction time closely. Small shifts can change conversion and impurity profiles. Stereochemical purity is critical because the D-enantiomer is the required configuration for downstream coupling. Specifications are normally fixed by the final drug-substance process, rather than by one universal intermediate limit. Chiral HPLC is the practical release tool; optical rotation is useful, but insufficient alone. The ICH Q6A guideline supports controlling stereochemical impurities when they may affect safety, quality, or performance.

A useful warning remains. A clean chiral chromatogram does not prove process robustness. Residual solvents, water content, regioisomers, and degradation products still require control. The WHO 2024 antibacterial development report also describes a limited innovation pipeline, reinforcing the need for efficient, reproducible intermediate manufacturing. Reliable producers therefore document mass balance, analytical recovery, and batch-to-batch enantiomeric purity. Controls must survive scale-up.

Pharmaceutical Applications Linked to Penicillin-Class Antibiotics

What Is 4-Hydroxy-D-Phenylglycine Used For?

4-Hydroxy-D-phenylglycine is mainly a chiral intermediate in pharmaceutical manufacturing. Its most recognized role is forming the side chain of penicillin-class antibiotics, especially amoxicillin. The molecule provides a para-hydroxyphenyl group and a D-configured amino acid structure. These features support selective coupling with 6-aminopenicillanic acid, creating the finished antibiotic framework. Manufacturers usually control protection, coupling, deprotection, and purification steps. Small process variations can affect optical purity and final yield.

The demand is linked to essential antibiotic production, not direct therapeutic use. The IQVIA Institute’s Global Use of Medicines 2024 report projects global medicine spending above 2.3 trillion US dollars by 2028. That figure reflects the wider pharmaceutical market, not this intermediate alone. Still, it shows the scale of manufacturing systems that depend on reliable chemical inputs. WHO’s Global Antibiotic Resistance Surveillance Report 2025 found that one in six laboratory-confirmed bacterial infections in 2023 showed resistance to antibiotic treatment. Quality matters.

Purity is critical.

In practice, pharmaceutical producers evaluate assay, stereochemical purity, residual solvents, water content, and trace metals. A weak assumption is that higher volume automatically means better supply security. It does not. Regulatory documentation, validated analytical methods, and consistent crystallization remain equally important. Public reports also rarely separate this intermediate from broader antibiotic supply chains, so precise market-size claims should be treated cautiously. Industry decisions require current supplier audits and batch-level evidence.

Quality Parameters: CAS 22818-40-2, Assay, and Impurity Control

What Is 4-Hydroxy-D-Phenylglycine Used For?

4-Hydroxy-D-phenylglycine, CAS 22818-40-2, is mainly used as a chiral intermediate in beta-lactam antibiotic synthesis. Its para-hydroxyphenyl structure supports downstream coupling reactions. In production, buyers usually assess more than a stated assay value. Identity, stereochemical purity, water content, residual solvents, and related substances can all affect process performance.

A practical specification often targets an assay of at least 98.0%, measured by validated HPLC. However, this is not a universal limit. Each application may require tighter control. Chiral HPLC can confirm the D-isomer and detect unwanted L-isomer contamination. LC-MS helps investigate unknown peaks. Karl Fischer testing gives a clearer water result than simple loss-on-drying, especially when the material is hygroscopic. Small differences matter.

The impurity profile deserves close review. Related aromatic compounds, unreacted starting materials, and degradation products should have defined reporting and identification thresholds. ICH Q3A(R2) provides a useful framework, although it may not directly replace a product-specific risk assessment. The FDA’s 2019 Drug Shortages Task Force report linked 62% of shortages to manufacturing and quality problems, showing why supplier qualification cannot rely on assay alone. A reliable batch record should include chromatograms, analytical methods, reference-standard details, storage conditions, and retest data. Some certificates still omit uncertainty information. That omission deserves scrutiny.

What Is 4-Hydroxy-D-Phenylglycine Used For?

Quality Parameters: CAS 22818-40-2, Assay, and Impurity Control

4-Hydroxy-D-phenylglycine, also known as D-p-hydroxyphenylglycine, is a chiral pharmaceutical intermediate used in the manufacture of semi-synthetic penicillin derivatives, including amoxicillin. The chart presents representative quality-control limits commonly applied to this type of pharmaceutical intermediate: assay is controlled at a minimum of 98.0%, while water, individual impurities, and total impurities are maintained below their respective maximum limits. Actual release criteria should be confirmed against the applicable manufacturing specification and analytical method.

FAQS

What is 4-Hydroxy-D-Phenylglycine?

It is a chiral aromatic amino acid derivative. It usually appears as a white or off-white crystalline solid.

What are its molecular formula and molar mass?

Its molecular formula is C8H9NO3. The anhydrous form has a molar mass of 167.16 g/mol.

What does the “D” label mean?

The “D” label describes the molecule’s three-dimensional configuration. It does not simply indicate purity.

Which functional groups does the molecule contain?

It contains a phenyl ring, a para-hydroxyl group, an amino group, and a carboxylic acid group. These groups provide useful reaction points.

What is its main application?

It serves as a specialized intermediate in pharmaceutical chemistry. Researchers also use it for chiral synthesis and analytical reference studies.

Is this compound a finished medicine?

No. It is a chemical intermediate, not a finished medicine. That distinction matters during handling, labeling, and quality review.

How can its reported mass or weighing result change?

The stated mass applies to the anhydrous molecular form. Hydrates, solvates, moisture, impurities, and assay methods may alter calculations.

How should its identity and quality be checked?

Review the certificate of analysis and current safety data sheet. Confirm configuration with suitable chromatography, optical rotation, or spectroscopy methods.

Why might two powder samples behave differently?

Particle size and moisture can affect dissolution and handling. Assuming identical behavior may be a mistake.

What should laboratory personnel document?

They should record storage conditions, protective equipment, testing methods, and sample details. Small records can prevent larger errors.

Conclusion

4-Hydroxy-D-Phenylglycine is an important chiral intermediate used in the manufacture of penicillin-class β-lactam antibiotics. With the molecular formula C8H9NO3 and a molar mass of 167.16 g/mol, it provides a specialized side-chain structure that contributes to the activity and performance of compounds such as amoxicillin and ampicillin. Its value comes from both its chemical functionality and its defined stereochemistry, which must be carefully preserved during pharmaceutical processing.

Industrial production may involve several conversion and purification steps designed to achieve high yield, consistent configuration, and reliable quality. Key quality considerations include the compound’s CAS number, 22818-40-2, assay strength, water content, residual solvents, and control of related impurities. Strict stereochemical purity and analytical testing are essential because even small variations can affect downstream antibiotic synthesis, product consistency, and compliance with pharmaceutical manufacturing standards.

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Charlotte
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Charlotte

Charlotte

Charlotte is a dedicated marketing professional at Shijiazhuang Pengnuo Technology Co., Ltd., a company known for its expertise in the research, development, production, and sales of pharmaceutical intermediates and fine chemical products since its establishment in 2020. With a strong academic......
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