Sphingomyelins（SM） (from bovine spinal cord) - ≥95%, natural bovine mixture , CAS No.85187-10-6

CAS: 85187-10-6 Cat. No.: S414640 Molecular Weight: 731.08 EC Number: 286-097-2 PubChem CID: 6453725

GRADE & PURITY ≥95%, natural bovine mixture

Synonyms

AKOS037645436 | ompenaclid [INN] | N-octadecanoylsphing-4-enine-1-phosphocholine | (2S,3R,4E)-3-hydroxy-2-(stearoylamino)octadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphate | SCHEMBL14889266 | SM d36:1 | 3,5-DIOXA-8-AZA-4-PHOSPHAHEXACOSAN-1-AMINIUM, 4-H

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Sphingomyelin (SM) is a principal sphingolipid in mammalian cell membranes. Its biological functions have been studied.

Application：

Sphingomyelin is suitable for use:
in the preparation of standard during the enzymatic measurement of plasma sphingomyelin levels
to study the binding of Vascular Anticoagulant α (VAC α) to planar phospholipid bilayers
to perform fluorescence polarization of PC16 (N-[α-N-palmitoyl-ε-N-(4-nitrobenz-2-oxa-1,3-diazole)-L-lysine]-2-aminoethanol-N- (trimethylaminoethanol) phosphate) in dispersions of co-sonicated lecithin and sphingomyelin
for reconstitution of viral ion channel protein M2 into liposomes
as a standard sample to define spectral fingerproint using Time-of-flight secondary ion mass spectrometry (ToF-SIMS)
to evaluate the contribution of various phospholipids to the formation of foam in the amniotic fluid

Specifications

Synonyms

AKOS037645436 | ompenaclid [INN] | N-octadecanoylsphing-4-enine-1-phosphocholine | (2S, 3R, 4E)-3-hydroxy-2-(stearoylamino)octadec-4-en-1-yl 2-(trimethylammonio)ethyl phosphate | SCHEMBL14889266 | SM d36:1 | 3, 5-DIOXA-8-AZA-4-PHOSPHAHEXACOSAN-1-AMINIUM, 4-H

Specifications & Purity

≥95%, natural bovine mixture

Biochemical and Physiological Mechanisms

Sphingomyelin is the second most abundant lipid and major sphingolipid component of HDL and the plasma membrane. It forms cholesterol-enriched lipid rafts. It has a key role in the availability of plasma membrane-free cholesterol.

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

≥95%

Product Properties

• pKa: pKa: 1.24

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP(=O)([O-])OCC[N+](C)(C)C)[C@@H](/C=C/CCCCCCCCCCCCC)O
• WGK Germany: 3
• PubChem CID: 6453725
• Molecular Weight: 731.08

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Ethanol: 10 mg/ml
• Molecular Weight: 731.100 g/mol
• XLogP3: 13.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 38
• Exact Mass: 730.599 Da
• Monoisotopic Mass: 730.599 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 50
• Formal Charge: 0
• Complexity: 826.000
• 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. Qiangqiang Li, Gang Chen, Dan Zhu, Wenwen Zhang, Suzhen Qi, Xiaofeng Xue, Kai Wang, Liming Wu.  (2022)  Effects of dietary phosphatidylcholine and sphingomyelin on DSS-induced colitis by regulating metabolism and gut microbiota in mice.  JOURNAL OF NUTRITIONAL BIOCHEMISTRY,      [PMID:35351615] [10.1016/j.jnutbio.2022.109004]

2. Wei Wei, Jin Cheng, Jie Yang, Chen Chen, Qingzhe Jin, Jie Song, Xingguo Wang.  (2021)  Phospholipid composition and fat globule structure change during low temperature storage of human milk.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2021.112050]

3. Chen Fangquan, Tang Hu, Lin Junhao, Xiang Limin, Lu Yanjiao, Kang Rui, Tang Daolin, Liu Jiao.  (2024)  Macropinocytosis inhibits alkaliptosis in pancreatic cancer cells through fatty acid uptake.  CARCINOGENESIS,      [PMID:39008332] [10.1093/carcin/bgae045]

4. Yang Yang, Xin Zhang, Jin Yang, Ziyan Wu, Junpeng Li, Ruilong Song, Chuang Meng, Guoqiang Zhu.  (2025)  N-(3-Oxododecanoyl)-Homoserine Lactone Induces Intestinal Barrier Damage in Piglets via the Lipid Raft-Mediated Apoptosis Pathway.  Veterinary Sciences,  12  (3): (233).  [PMID:40266950] [10.3390/vetsci12030233]

5. Zhirong Li, Lulu Zhang, Zhanzhong Wang, Xiongli Kang, Huiying Jin, Wenjie Zhao, Jun Zhang, Haiquan Su.  (2024)  Quantification of Phosphatidylserine Molecules on the Surface of Individual Cells Using Single-Molecule Force Spectroscopy.  ANALYTICAL CHEMISTRY,      [PMID:38173079] [10.1021/acs.analchem.3c03517]

6. Jinlei Yang, Tianyi Liao, Pingping Zhang, Runsong Cheng, Jing Wang, Siyuan Pan, Murong Du, Boya Zhao, Weiliang Liu, Liying Yan, Sichun Zhang, Xinrong Zhang.  (2025)  On-Valve μSFE-SFC-MS Enables Fast Analysis of Single Oocyte Lipidome.  ANALYTICAL CHEMISTRY,      [PMID:40738860] [10.1021/acs.analchem.5c03365]