phosphatidylserine 70%

 

1. Chemical Identity

• IUPAC Name: 1,2-diacyl-sn-glycero-3-phospho-L-serine

• Molecular Formula: C₄₂H₈₂NO₁₀P (representative for soy-derived with C16:0/C18:2 fatty acids)

• CAS Number: 51446-62-9 (from soy), 137637-40-4 (from bovine cortex)

2. Source & Production Methods

Primary Sources:

• Soybean-derived (≥98% purity): Predominant commercial source using enzymatic transphosphatidylation of phosphatidylcholine

• Sunflower-derived: Emerging alternative with different fatty acid profile

• Bovine cortex-derived: Historical source, now largely replaced due to BSE concerns

Manufacturing Processes:

1. Enzymatic Conversion (Commercial standard):

   • Phospholipase D-mediated transphosphatidylation

   • Substrate: High-purity soybean phosphatidylcholine

   • Serine donor: L-serine

   • Yield: Typically >90% conversion efficiency

2. Extraction & Purification:

   • Solvent extraction (food-grade ethanol/hexane)

   • Column chromatography purification

   • Molecular distillation for concentration

   • Ultra-filtration for endotoxin control

3. Chemical Properties

Physical Characteristics:

• Appearance: White to light yellow powder or viscous liquid

• Solubility:

  • Soluble in chloroform, methanol, dimethyl sulfoxide

  • Insoluble in water, acetone, hexane

• Melting Point: 180-185°C (decomposes)

• Hygroscopicity: Moderate; requires desiccant protection

Fatty Acid Composition (Typical Soy Source):

• Palmitic acid (C16:0): 8-12%

• Stearic acid (C18:0): 2-4%

• Oleic acid (C18:1): 8-12%

• Linoleic acid (C18:2): 60-70%

• Linolenic acid (C18:3): 5-8%

4. Specifications & Quality Standards

Pharmaceutical-Grade Parameters:

Identity Verification:

• FTIR spectroscopy: Characteristic peaks at 3300-2500 cm⁻¹ (NH₃⁺), 1735 cm⁻¹ (C=O), 1220 cm⁻¹ (P=O)

• NMR spectroscopy: ¹H and ³¹P NMR for structural confirmation

• Mass spectrometry: ESI-MS for molecular weight determination

5. Stability & Storage

Degradation Pathways:

• Hydrolysis of ester bonds (acid/alkali catalyzed)

• Oxidation of unsaturated fatty acids

• Phosphodiester bond cleavage

Stabilization Strategies:

• Antioxidant addition (tocopherols, ascorbyl palmitate)

• Nitrogen blanketing during processing

• Cold chain storage (2-8°C recommended)

• Light-protected packaging (aluminum foil)

Shelf Life:

• Unopened, proper storage: 24 months

• Opened containers: 6 months maximum

• Reconstituted solutions: 24 hours at 2-8°C

6. Applications

Pharmaceutical Uses:

• Cognitive enhancement: 100-300 mg/day for memory support

• Sports nutrition: 400-800 mg/day for cortisol modulation

• Geriatric formulations: Combined with omega-3s for brain health

• Dosage forms: Softgels, powders, emulsions, liposomal preparations

Delivery Systems:

• Liposomal encapsulation (enhanced bioavailability)

• Self-emulsifying drug delivery systems (SEDDS)

• Nanoparticle formulations for blood-brain barrier penetration

7. Safety & Regulatory Status

Regulatory Approvals:

• FDA: Generally Recognized As Safe (GRAS) for specific uses

• EFSA: Approved health claims for cognitive function (2010)

• Health Canada: Natural Product Number (NPN) issued

• Pharmacopoeial Standards: USP-NF monograph under development

Toxicology Profile:

• LD₅₀: >5000 mg/kg (rat, oral)

• NOAEL: 420 mg/kg/day (90-day study)

• Mutagenicity: Negative (Ames test)

• Reproductive toxicity: No adverse effects at recommended doses

8. Analytical Methods

Quantification Techniques:

1. HPLC-ELSD: Primary method for purity assessment

2. ³¹P-NMR: Gold standard for positional isomer determination

3. TLC-densitometry: Rapid screening method

4. Enzymatic assays: Specific for PS quantification in mixtures

Impurity Profiling:

• Related phospholipids (PC, PE, PI): <2% each

• Lysophosphatidylserine: <0.5%

• Free fatty acids: <1%

• Glycerol: <0.5%