(S)-3-Amino-3-phenylpropanoic acid RC00260

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

Here is a detailed product description for  (S)-3-Amino-3-phenylpropanoic acid  (CAS 40856-44-8):

1. Chemical Identification & Structure

Chemical Name:  (S)-3-Amino-3-phenylpropanoic acid

Synonyms:

(S)-β-Amino-β-phenylpropionic acid

(S)-3-Amino-3-phenylpropionic acid

(S)-β-Phenyl-β-alanine

(S)-3-Phenyl-β-alanine

CAS Registry Number:  40856-44-8

Molecular Formula:  C₉H₁₁NO₂

Molecular Weight:  165.19 g/mol

InChIKey:  OWZLFQOOQZMMCV-VIFPVBQESA-N

2. Chemical Classification

Enantiopure non-proteinogenic β-amino acid

β-Amino acid derivative

Aryl-substituted alanine analog

Chiral building block

3. Physical & Chemical Properties

Appearance:  Typically a white to off-white crystalline powder.

Melting Point:  Decomposes around 210-215 °C (exact value can vary; decomposition is common).

Specific Rotation:  [α]D²⁰ typically reported around -30° to -35° (c = 1, in H₂O).  Important: Rotation is solvent and concentration dependent; always check the certificate of analysis.

Solubility:

Moderately soluble in water.

Soluble in polar organic solvents (e.g., methanol, ethanol, DMSO).

Poorly soluble in non-polar organic solvents (e.g., hexane, diethyl ether).

Acidity/Basicity:  Exists as a zwitterion at neutral pH. Contains a carboxylic acid group (pKa ~2-3) and an amino group (pKa ~9-10).

Chirality:  Single enantiomer, (S)-configuration at the β-carbon.

Stability:  Stable under normal storage conditions. Sensitive to strong oxidizing agents, strong acids, and strong bases. Hygroscopic.

4. Synthesis & Purity

Synthesis Routes:  Commonly synthesized via:

Asymmetric hydrogenation of β-enamino ester precursors.

Enzymatic resolution of the racemate (DL-3-Amino-3-phenylpropanoic acid).

Chiral pool synthesis from enantiopure precursors.

Typical Purity:  Available from commercial suppliers in high chemical purity (>98%) and high enantiomeric excess (ee) (>98% ee, often >99% ee).

Analysis:  Identity and purity confirmed by techniques like NMR (¹H, ¹³C), FT-IR, HPLC, UPLC, and elemental analysis (CHN). Enantiomeric excess determined by chiral HPLC or chiral GC using appropriate columns.

5. Applications & Uses

Pharmaceutical Intermediates:  Key chiral building block in the synthesis of bioactive molecules, particularly anticonvulsant drugs.  Crucially, it is the immediate precursor for the synthesis of (S)-α-Ethyl-2-oxo-1-pyrrolidineacetamide, the core structure of the blockbuster antiepileptic drug Levetiracetam (Keppra®) and related analogues (Brivaracetam, Seletracetam).

Chemical Biology:  Used to study peptide structure/function relationships by incorporating β-amino acids into peptides to modulate stability, conformation, and biological activity.

Enzyme Substrate/Inhibitor Studies:  Probe for enzymes involved in amino acid metabolism or transport.

Ligand Synthesis:  Potential building block for chiral catalysts or ligands used in asymmetric synthesis.

Research Reagent:  General reagent in organic synthesis and medicinal chemistry research for introducing the chiral (S)-3-amino-3-phenylpropanoic acid moiety.

6. Storage & Handling

Storage Conditions:  Store tightly sealed in a cool (2-8°C), dry place, protected from light and moisture. Under inert atmosphere (e.g., argon or nitrogen) for long-term storage is recommended to maximize stability.

Handling Precautions:  Handle in a well-ventilated laboratory using standard personal protective equipment (PPE) - lab coat, safety glasses, nitrile gloves. Avoid generating dust. Avoid contact with skin, eyes, and clothing. Avoid inhalation of dust.

Stability:  Stable for several years when stored properly. Check appearance and specific rotation periodically if stored long-term.

7. Safety Information (General - Consult SDS for Specific Batch)

GHS Hazard Statements (Typical):  Not classified as hazardous under normal laboratory use. May cause skin/eye irritation. May be harmful if swallowed or inhaled (dust).

Precautionary Statements (P Phrases Typical):  P261 (Avoid breathing dust/fume/gas/mist/vapours/spray), P264 (Wash hands thoroughly after handling), P271 (Use only outdoors or in a well-ventilated area), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P302+P352 (IF ON SKIN: Wash with plenty of water), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing).

First Aid:  Skin contact - Wash thoroughly with soap and water. Eye contact - Flush cautiously with water for at least 15 minutes, lifting upper and lower eyelids. Seek medical attention if irritation persists. Ingestion - Rinse mouth. Do NOT induce vomiting. Seek medical attention. Inhalation - Move to fresh air. Seek medical attention if respiratory irritation occurs.

Disposal:  Dispose of in accordance with all applicable local, regional, national, and international regulations. Treat as chemical waste.