Pharmaceutical Grade
Phenylalanine sodium salt
CAS Number
16480-57-2
Molecular Formula
C₉H₁₀NNaO₂
Molecular Weight
187.17 g/mol
Purity
≥99.0%
Appearance
White crystalline powder
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Product Description
Phenylalanine sodium salt, also known as sodium phenylalaninate or sodium L-phenylalaninate depending on its stereochemistry, is the sodium salt of phenylalanine. It is derived from L-phenylalanine, where the carboxyl group is deprotonated and neutralized by a sodium ion. This compound features an aromatic phenyl ring, an amino group that can be protonated or free depending on the pH, and a carboxylate group bound to Na⁺. Phenylalanine sodium salt is freely soluble in water and slightly soluble in ethanol, making it a more water-soluble derivative of phenylalanine. It is used as a nutritional supplement to potentially influence thyroid hormone and melanin synthesis. Additionally, it serves as a valuable reagent in biochemical research and for the preparation of culture media.
Synthesis Methods
- Produced by neutralizing L-phenylalanine with a sodium base (e.g., sodium hydroxide) in an aqueous solution: C9H11NO2 (L-Phenylalanine) + NaOH → C9H10NNaO2 + H2O.
- The reaction mixture is purified, and the product is isolated via evaporation crystallization or similar processes.
- No complex synthesis protocols or dedicated patents; inferred as a simple neutralization, potentially used as an intermediate in purification (e.g., manipulating solubility for separation).
- Parent acid (L-phenylalanine) synthesis includes Strecker method (phenylacetaldehyde with ammonium/cyanide, followed by hydrolysis) or biocatalysis (e.g., using phenylalanine ammonia lyase for high yield and optical purity).
Uses and Applications
- Pharmaceutical Industry: Used in intravenous (IV) nutrition/total parenteral nutrition (TPN) solutions for high solubility and biocompatibility; as an excipient in drug formulations to improve solubility, stability, pH buffering, and bioavailability; not a primary active ingredient but a functional additive.
- Food and Beverage Industry: In dietary supplements or protein shakes for bioavailability; potential precursor or intermediate in aspartame synthesis (though aspartame uses methyl ester of phenylalanine); flavor enhancer (umami/savory taste) and sodium replacer to reduce total sodium content in foods like processed meats without loss of saltiness.
- Biochemical Research: Component in cell culture media for protein synthesis; buffer preparation; studies on protein synthesis, enzyme activity, gastrointestinal effects (e.g., appetite, gastric emptying, hormone secretion like CCK/GLP-1); metabolic research as a precursor to melanin, dopamine, norepinephrine, and thyroxine.
- Nutraceutical/Supplement: Affects thyroid hormone and melanin synthesis; used for vitiligo (with UV treatment), mood improvement/depression, chronic pain, ADHD, appetite suppression (evidence inconclusive for some); building block for proteins.
- Other: In scientific research for culture medium preparation; potential in food science as a dual-purpose additive for flavor and sodium reduction; inferred as a non-commodity intermediate in manufacturing processes.
Names and Synonyms
- Chemical Name: Sodium (2S)-2-amino-3-phenylpropanoate
- Common Names: Phenylalanine sodium; Phenylalanine sodium salt; Sodium phenylalaninate; Sodium L-phenylalaninate; Sodium 3-phenyl-L-alaninate; L-Phenylalanine sodium salt
- Other Synonyms: L-Phenylalanine sodium; Sodium (L)-phenylalaninate
Identifiers
- PubChem CID: 23677936
- CAS Number: 16480-57-2
- European Community (EC) Number: 240-534-3
- UNII: M67R83MDEE
- DSSTox Substance ID: DTXSID10167810
- Nikkaji Number: J27.577H
- Wikidata: Q27283548
- InChI: InChI=1S/C9H11NO2.Na/c10-8(9(11)12)6-7-4-2-1-3-5-7;/h1-5,8H,6,10H2,(H,11,12);/q;+1/p-1/t8-;/m0./s1
- InChIKey: ZRVUAXXSASAVFG-QRPNPIFTSA-M
- SMILES: C1=CC=C(C=C1)CC@@HN.[Na+]
Structural Information
- Molecular Formula: C9H10NNaO2
- Structure Breakdown: Derived from L-phenylalanine (C9H11NO2), consisting of a benzene (phenyl) ring, an amino group (-NH2), a propanoate chain, and a carboxylate group (-COO⁻) electrostatically bound to a sodium cation (Na⁺). The carboxylic acid group of phenylalanine loses a proton to form the anion, balanced by Na⁺.
- Stereochemistry: Primarily the L-enantiomer (levorotatory, naturally occurring and biologically relevant form); the formula does not inherently specify stereochemistry, so it could refer to L-, D-, or DL-forms.
- 2D Structure: Available as a standardized depiction (processed through chemical structure standardization).
- 3D Conformer: Computed (not experimentally determined), based on a protein-bound model; parent compound (L-Phenylalanine) CID: 6140.
- Biologic Description: Depicted as a biologic with line notations including IUPAC Condensed (H-Phe-OH.Na+), Sequence (F), and IUPAC (L-phenylalanine sodium salt).
- Functional Groups: Aromatic phenyl ring, amino group (-NH2, protonated or free depending on pH), carboxylate group (-COO⁻ bound to Na⁺).
Physical and Chemical Properties
- Molecular Weight/Molar Mass: 187.17 g/mol (average); exact mass 187.06092284 Da; monoisotopic mass 187.06092284 Da.
- Physical State: White to off-white crystalline powder (odorless, slightly bitter taste for parent acid).
- Solubility: Highly soluble in water (due to ionic nature; enhances water-solubility compared to free phenylalanine); slightly soluble in ethanol; much less soluble in organic solvents like acetone. Note: One reported value of 11.0 mg/mL (0.011 g/L) is likely erroneous based on chemical principles (salting-in effect and ionic character suggest higher solubility than parent acid's 9.97-68.9 g/L temperature-dependent range).
- Melting Point/Decomposition: Decomposes upon heating (no sharp melting point); parent acid decomposes at 270-283 °C.
- pH (in Solution): Basic (pH > 7) as the carboxylate anion acts as a conjugate base of a weak acid.
- pKa: Acidic pKa = 2.47; basic pKa = 9.45 (similar to parent acid's pK1=2.58, pK2=9.24).
- Hygroscopicity: Likely hygroscopic (absorbs moisture from air).
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Rotatable Bond Count: 3
- Topological Polar Surface Area: 66.2 Ų
- Heavy Atom Count: 13
- Formal Charge: 0
- Complexity: 158 (computed using Bertz/Hendrickson/Ihlenfeldt formula)
- Isotope Atom Count: 0
- Defined Atom Stereocenter Count: 1
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Covalently-Bonded Unit Count: 2
- Compound Is Canonicalized: Yes
- Stability and Reactivity: Stable under normal storage conditions; incompatible with strong oxidizing agents; emits toxic fumes (e.g., nitrogen oxides) upon decomposition when heated.
- Other Computed Properties: Improves handling, stability, and bioavailability compared to free amino acid due to salt form.
Safety and Handling
- Generally Recognized as Safe (GRAS): Considered safe for consumption in regulated amounts as a salt of a natural amino acid.
- Precautions: Standard laboratory handling (avoid dust inhalation, use PPE like gloves/safety glasses); protect from light, store tightly closed in a cool place; avoid contact with strong oxidants.
- Side Effects: For supplements (related to phenylalanine content): Anxiety, headache, constipation; topical cream possibly safe short-term.
- Key Health Concern: Phenylketonuria (PKU) warning required—accumulation toxic to brain; products must label for PKU patients (genetic disorder impairing phenylalanine metabolism, leading to intellectual disability, seizures if untreated).
- Drug Interactions: Competes with Levodopa (reduces effectiveness for Parkinson's); increases tyramine with MAOIs (risk of hypertensive crisis); decreases Baclofen absorption.
- Contraindications: High levels risky in pregnancy (birth defects); may exacerbate tardive dyskinesia in schizophrenia; seek medical attention if inhaled/ingested.
- Toxicology: Emits toxic fumes upon decomposition; side effects from excess include worsened symptoms in special populations.
Regulatory and Commercial Information
- Regulatory Status: Governed by rules for L-phenylalanine as a food additive/excipient; FDA affirms safety for general population (e.g., in aspartame since 1974); must carry PKU warnings; no specific EMA/FDA approval as a standalone drug (unlike related sodium phenylbutyrate for urea cycle disorders).
- Commercial Landscape: Limited availability (not a bulk commodity); market dominated by free L-phenylalanine; primarily an in-situ intermediate for specialized processes; suppliers focus on parent acid.
- Vendors: Available from chemical vendors (randomized list in PubChem; no endorsements); multiple products varying in amount/purity; linked to PubChem Substance IDs for details.