Sphingomyelin (Milk, Bovine) - ≥99% , CAS No.475662-40-9

CAS: 475662-40-9 Cat. No.: S130561 PubChem CID: 46891684

GRADE & PURITY ≥99%

Synonyms

C23 Sphingomyelin | SM(d18:1/23:0) | N-(tricosanoyl)-sphing-4-enine-1-phosphocholine | Sphingomyelin (Milk, Bovine) | N-tricosanoylsphing-4-enine-1-phosphocholine

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

As a major constituent of cell membranes, sphingomyelin is found at particularly high concentrations in the membranes of nerve cells (in the myelin sheaths) and red blood cells. It was previously thought to have a purely structural role, similar to the function of phosphatidylcholine, through intermolecular interactions mediated by the 2-amide group, the 3-hydroxy group and the 4,5-trans double bond of the sphingoid base. However, it is now appreciated that sphingomyelin has a high affinity for cholesterol and that these two lipids pack tightly into liquid-ordered domains among a liquid-disordered phase to form lipid rafts. These membrane microdomains are thought to function as signaling platforms that regulate the localization and interactions of proteins. But sphingomyelin does not just influence signaling as a component of lipid rafts — it is also a precursor to ceramides and other sphingolipid metabolites that comprise the sphingomyelin cycle or sphingolipid network.

Specifications

Synonyms

C23 Sphingomyelin | SM(d18:1/23:0) | N-(tricosanoyl)-sphing-4-enine-1-phosphocholine | Sphingomyelin (Milk, Bovine) | N-tricosanoylsphing-4-enine-1-phosphocholine

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 504770831
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504770831
• Isomeric SMILES: CCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O
• PubChem CID: 46891684

Chemical and Physical Properties

• Molecular Weight: 801.200 g/mol
• XLogP3: 16.100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 43
• Exact Mass: 800.677 Da
• Monoisotopic Mass: 800.677 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 55
• Formal Charge: 0
• Complexity: 903.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Miao Guan, Lei Li, Yang Zheng, Shaoxing Dai, Runling Wei, Zhenglong Sun.  (2026)  Analysis and characterization of a novel metallophosphoesterase from Akkermansia muciniphila involved in lipid degradation.  Biochemistry and Biophysics Reports,      [PMID:41550492] [10.1016/j.bbrep.2025.102437]