Palmitoyl Sphingomyelin
Palmitoyl Sphingomyelin (CAS No.: 6254-89-3) is a naturally occurring sphingolipid widely distributed in mammalian cell membranes, where it contributes to membrane architecture, lipid raft formation, and cellular signaling processes. As a major component of plasma membranes and lipoprotein particles, including low-density lipoprotein-associated liposomes, it plays critical roles in modulating membrane fluidity, stability, and protein organization, thereby influencing signal transduction pathways, cell recognition, and lipid metabolism. Palmitoyl sphingomyelin is particularly relevant in neurological and metabolic research, as alterations in its metabolism have been associated with neurodegenerative disorders, metabolic syndromes, and lysosomal storage diseases, while its differential abundance has also been observed in cancer-related contexts such as colorectal and prostate malignancies. Mechanistically, it participates in sphingolipid metabolic pathways that regulate the balance of bioactive lipids, including ceramide and sphingosine-1-phosphate, thereby indirectly affecting apoptosis, proliferation, and inflammatory signaling. In experimental systems, it is frequently employed in model membrane studies to investigate lipid raft dynamics and membrane organization, as well as in cell-based and animal models examining lipid metabolism and disease pathology; the concentrations or doses used in experiments typically depend on specific experimental designs and research objectives, with activity generally evaluated in the nanomolar to micromolar range based on related sphingolipid analogs.
| Physical Appearance | A solid |
| Storage | -20°C |
| M.Wt | 703.04 |
| Cas No. | 6254-89-3 |
| Formula | C39H79N2O6P |
| Synonyms | Palmitoyl Sphingomyelin; N- Palmitoyl- D- erythro - Sphingosylphosphorylcholine; SM(d18:1/16:0); Sphingomyelin (d18:1/16:0) |
| Solubility | ≥2.71 mg/mL in DMSO with gentle warming and ultrasonic; ≥53.1 mg/mL in EtOH; insoluble in H2O |
| Chemical Name | (2S,3R,E)-3-hydroxy-2-palmitamidooctadec-4-en-1-yl (2-(trimethylammonio)ethyl) phosphate |
| Canonical SMILES | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCCCCCCCCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |







