Phosphatidylserine

Inquiry

Cat Number

PIPE-0761

CAS Number

51446-62-9

If you have any other questions, please contact our experts.

Product Detail Description Scientific Support Advanced Innovations Customer Q&A

CAS Number

51446-62-9

EINECS

935-500-6

Storage

Store at 2-8°C

Synonyms

Distearoylphosphatidylserine; 1446756-47-3; 394XK0IH40; (2S)-2-amino-3-[[(2R)-2,3-di(octadecanoyloxy)propoxy]-hydroxyphosphoryl]oxypropanoic acid; Phosphatidyl Serines

Molecular Formula

C42H82NO10P

Molecular Weight

792.1

Smiles

CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC[C@@H](C(=O)O)N)OC(=O)CCCCCCCCCCCCCCCCC

Appearance

Light yellow to yellow powder

Boiling Point

560.3±60.0°C at 760 mmHg (Predicted)

Relative Density

1.4±0.1

General Description

Phosphatidylserine is a glycerophospholipid and a primary anionic phospholipid, particularly abundant in the inner leaflet of the plasma membrane in neural tissues. It is synthesized from phosphatidylcholine or phosphatidylethanolamine by exchanging the base head group with serine, a reaction catalyzed by phosphatidylserine synthase-1 and -2. As a major structural component of neuronal membranes, it is crucial for maintaining cellular function and signaling.

Mechanism of Action

Phosphatidylserine acts as a cofactor for several essential enzymes that participate in signaling pathways. Its exposure on the outside of the cell surface is essential for eliminating apoptotic cells and initiating the blood clotting cascade. By incorporating into cell membranes, it helps maintain membrane fluidity and supports the function of membrane-bound proteins, including receptors and ion channels, which are critical for neurotransmitter release and signal transduction.

Application

Clinically, Phosphatidylserine supplementation has been studied for its potential benefits in patients with cognitive decline, Alzheimer's disease, and age-related memory impairment. It is thought to improve the release and availability of acetylcholine, a neurotransmitter involved in memory and learning. Supplementation has also shown benefits for conditions like ADHD, Parkinson's disease, and depression by reducing neuroinflammation and acting as a neuroprotective factor.

This review discusses the biology of phosphatidylserine (PS) externalization as a dominant and evolutionarily conserved immunosuppressive signal. PS exposure on apoptotic cells promotes tolerance and prevents immune activation under physiological conditions. Pathologically, viruses, microorganisms, and parasites hijack PS to facilitate infection and latency. In the tumor microenvironment, PS dysregulation antagonizes antitumor immunity. The authors argue that agents targeting PS could have significant therapeutic value in both cancer and infectious disease.

Fig. 1 Models for the different forms of PS externalization. (Birge RB, et al., 2016)

References

Birge RB, et al. Phosphatidylserine is a global immunosuppressive signal in efferocytosis, infectious disease, and cancer. Cell Death Differ. 2016;23(6):962-978.

In Plasmodium‑infected mice, plasmablast formation is linked to hemolysis‑induced phosphatidylserine (PS) exposure on damaged RBCs and inflammatory cues. The PS receptor Axl is critical for optimal plasmablast formation. Blocking PS limits plasmablast expansions and reduces parasite burden. Virus and Trypanosoma infections that cause hemolytic anemia also induce exuberant plasmablast responses. Strategies targeting PS exposure and polyclonal B cell activation may improve immune responses against Plasmodium and other anemia‑associated infections.

Fig. 2 Plasmablasts can expand independently of antigen–BCR interactions. (Vijay R, et al., 2021)

References

Vijay R, et al. Hemolysis-associated phosphatidylserine exposure promotes polyclonal plasmablast differentiation. J Exp Med. 2021;218(6):e20202359.

Does Phosphatidylserine require protection from oxygen and heat during long-term storage?

Yes, it is highly susceptible to oxidation due to unsaturated fatty acid chains. Store in airtight containers under inert gas (nitrogen) at 2-8°C to prevent rancidity.

Is Phosphatidylserine stable in powder form under high-humidity conditions?

It is hygroscopic and can absorb moisture, leading to stickiness and microbial growth. Store in tightly sealed, moisture-proof containers with desiccant.

What is the recommended shipping condition for Phosphatidylserine bulk orders?

Shipments must be temperature-controlled (2-8°C) with light protection.

How is the oxidation impurity phosphatidylserine hydroperoxide monitored?

Peroxide value and thiobarbituric acid reactive substances (TBARS) are measured using validated assays to ensure oxidation levels remain within specifications.