O-Phosphorylethanolamine (CAS 1071-23-4): Natural Phosphoamine Metabolite — Full Analysis of Biosynthesis, Biochemical Functions and Industrial Applications

1、 Product Overview

O-Phosphorylethanolamine (also known as phosphoethanolamine, colamine phosphate, or 2-aminoethyl dihydrogen phosphate) is a naturally occurring phosphoamine metabolite that plays a fundamental role in cellular phospholipid metabolism. As the direct biosynthetic precursor to phosphatidylethanolamine (PE) — one of the most abundant phospholipids in mammalian cell membranes — its greatest value lies in its ability to serve as both a key biochemical intermediate and a versatile industrial building block. Unlike synthetic analogues, this natural zwitterionic compound offers exceptional biocompatibility and bioactivity, making it indispensable in biochemical research, pharmaceutical development, cosmetic formulations, nutritional supplements, and industrial biotechnology.

2. Basic Product Information

1. Product Name: O-Phosphorylethanolamine (2-Aminoethyl dihydrogen phosphate)

2. CAS NO.: 1071-23-4

3. Molecular Formula: C₂H₈NO₄P

4. Molecular Weight: 141.06

5. Structural Formula:

6. Purity: ≥ 99%

7. Appearance: White to off-white crystalline powder

8. Melting Point: 241-243°C (decomposes)

9. Solubility: Freely soluble in water; slightly soluble in methanol and ethanol; practically insoluble in acetone, chloroform, and ether

10. pH (1% aqueous solution): 4.0-6.0

11. Loss on Drying: ≤ 1.0%

12. Storage Conditions: Store at room temperature in a tightly closed container, protected from light and moisture

13. Product Manager Email: selina@coreychem.com

3、 Frequently Asked Questions (FAQ)

Question 1: What are the basic physical properties of O-Phosphorylethanolamine (CAS NO.: 1071-23-4)?

This product is a white crystalline powder at room temperature. Its melting point is 241-243°C (decomposes). It is freely soluble in water, slightly soluble in methanol and ethanol, and practically insoluble in acetone, chloroform and ether. It needs to be stored at room temperature, kept in a tightly closed container, protected from light and moisture.

Question 2:What are the common synthesis methods for this compound?

1. Phosphorylation of ethanolamine (traditional method)
Prepared by reacting ethanolamine with phosphoric acid or phosphorus oxychloride under controlled conditions. This method is relatively straightforward but requires careful control of reaction temperature and pH to avoid side reactions and polymerization.
2. Debenzylation of protected intermediates (alternative route):
Ethanolamine is first protected with benzyl groups, then phosphorylated, followed by catalytic hydrogenation to remove the protecting groups. This route provides higher purity but involves more steps and higher production costs.

Question 3:What is the main feature of this product in terms of application?

Its core application feature is as a “natural phospholipid precursor” and “biological buffer component”. Simply put, its most unique value lies in its role as a key intermediate in the biosynthesis of phospholipids, serving as a precursor for phosphatidylethanolamine. It is widely used as a component in cell culture media, a substrate for enzyme assays (e.g., alkaline phosphatase), and a raw material for the synthesis of phospholipid derivatives in pharmaceutical and cosmetic formulations.

Question 4:What is the solubility and stability of this product in different solvents? Can it be used in aqueous systems?

This product exhibits excellent water solubility due to its zwitterionic nature. It dissolves freely in water to form clear solutions. It shows moderate solubility in hot methanol and ethanol but is practically insoluble in organic solvents such as acetone, chloroform, and ether. The aqueous solution is stable at neutral pH but may hydrolyze under strong acidic or alkaline conditions. It is recommended to prepare fresh solutions when used in biological assays and avoid exposure to high temperatures for extended periods.

Question 5:Is this product suitable for use as a buffer component in biological systems? What are the considerations?

Yes, it is commonly used as a buffer component in biological and biochemical applications due to its good biocompatibility. However, it should be noted that its buffering capacity is limited to pH ranges around its pKa values. When used in cell culture media, it can serve as a phosphate source and a precursor for phospholipid synthesis. It is recommended to sterilize solutions by filtration rather than autoclaving, as high-temperature treatment may cause degradation. For best results, prepare fresh solutions and store at 2-8°C for short-term use, or freeze at -20°C for long-term storage.

4、 Application Cases

Application 1:What is the role of O-Phosphorylethanolamine (CAS NO.: 1071-23-4) in the field of biochemical research?

O-Phosphorylethanolamine is a natural phosphoamine metabolite that plays a crucial role as a key intermediate in phospholipid biosynthesis. It serves as the direct precursor for the synthesis of phosphatidylethanolamine (PE), one of the most abundant phospholipids in mammalian cell membranes. In biochemical research, it is widely used as a substrate for alkaline phosphatase (ALP) activity assays, where the enzymatic hydrolysis releases inorganic phosphate and ethanolamine, allowing for convenient colorimetric or fluorometric detection. Additionally, it is utilized in cell culture media as a phosphate source and lipid precursor, and in neuroscience research for studying ethanolamine metabolism and its involvement in synaptic membrane formation.

Application 2:What is the role of the product in the field of pharmaceutical manufacturing?

O-Phosphorylethanolamine serves as an important pharmaceutical intermediate and active pharmaceutical ingredient (API) in the development of drugs targeting metabolic and neurological disorders. In the pharmaceutical field, it is used as a raw material for the synthesis of phospholipid-based drug delivery systems, including liposomes and lipid nanoparticles, where its polar head group imparts excellent biocompatibility and membrane fusogenicity. It is also utilized in the formulation of parenteral nutrition solutions, providing a bioavailable source of ethanolamine and phosphate for patients with liver dysfunction or metabolic deficiencies. Furthermore, its structural similarity to phosphorylcholine makes it a valuable building block for designing novel compounds targeting the Kennedy pathway in phospholipid metabolism, with potential applications in treating Alzheimer’s disease and other neurodegenerative conditions.

Application 3:What is the role of the product in the field of cosmetic and personal care ingredients?

O-Phosphorylethanolamine is a highly valued functional ingredient in advanced cosmetic formulations, particularly in products designed for skin barrier repair and anti-aging. As a natural component of cell membranes, it contributes to the structural integrity and fluidity of the epidermal lipid barrier, enhancing skin hydration and resilience. In skincare formulations, it acts as a mild moisturizing agent and skin-conditioning additive, promoting the regeneration of damaged skin tissues and improving the overall texture and appearance of the skin.

Its zwitterionic nature also allows it to function as a natural emulsifier in oil-in-water emulsions, stabilizing formulations without the need for synthetic surfactants. Additionally, its phosphorus content provides a valuable source of bioavailable phosphate for cellular energy metabolism, making it an ideal ingredient in revitalizing and anti-aging creams, serums, and lotions.

Application 4:What is the role of the product in the field of dietary supplements and nutrition?

O-Phosphorylethanolamine is recognized as a bioavailable source of ethanolamine and phosphorus, making it a valuable component in dietary supplements targeted at cognitive health, liver support, and overall cellular wellness. Ethanolamine is an essential precursor for the synthesis of phospholipids, which are critical for maintaining the structural integrity and function of cell membranes, particularly in brain and hepatic tissues. Supplementation with O-phosphorylethanolamine can help support normal phospholipid turnover, potentially benefiting individuals with compromised liver function, neurodegenerative conditions, or age-related cognitive decline. It is also included in specialty sports nutrition formulations to support muscle repair and energy metabolism, as its phosphate group is directly involved in ATP production and cellular signaling pathways.

Application 5:What is the role of the product in the field of industrial biotechnology?

O-Phosphorylethanolamine finds utility in industrial biotechnology as a key raw material for the enzymatic production of phospholipids and other bioactive phosphate esters.

Through enzymatic phosphorylation or transphosphatidylation reactions, it serves as a donor substrate for the synthesis of various phospholipid derivatives, including phosphatidylethanolamine, phosphatidylserine, and other functional lipids used in food, feed, and pharmaceutical industries. It is also utilized in the development of biosensors for detecting alkaline phosphatase activity, enabling its application in clinical diagnostics and environmental monitoring.

Moreover, its ability to chelate metal ions allows it to function as a mild corrosion inhibitor in aqueous systems, where it can be incorporated into environmentally friendly formulations for metal surface protection in cooling water systems and industrial cleaning applications.

5、 Safety and Storage

1. Store in a cool, well-ventilated area and keep the container tightly sealed.

2. Keep away from light and moisture. Store in a dry place at room temperature. For long-term storage, refrigeration at 2-8°C is recommended.

3. Store separately from strong oxidizers, strong acids, and strong bases to avoid decomposition or undesired reactions.

4. Handle with standard laboratory precautions. Use appropriate personal protective equipment (PPE) such as gloves, safety goggles, and lab coats. Avoid dust formation and inhalation.

5. In case of contact with skin or eyes, rinse immediately with plenty of water and seek medical attention if irritation persists.

6、Product Manager Information

Product Manager: Selina
Email: selina@coreychem.com