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Merck
CN

860062C

Avanti

Brain SM

Avanti Research™ - A Croda Brand

别名:

18:0 SM; Octadecanoyl Sphingomyelin; N-octadecanoyl-D-erythro-sphingosylphosphorylcholine; N-(octadecanoyl)-sphing-4-enine-1-phosphocholine

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关于此项目

化学文摘社编号:
383907-91-3
MDL number:
MFCD02259130
UNSPSC Code:
12352211
NACRES:
NA.25

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产品名称

Brain SM, Avanti Research™ - A Croda Brand

SMILES string

[P](=O)([O-])(OC[C@H](NC(=O)CCCCCCCCCCCCCCCCC)[C@H](O)\C=C\CCCCCCCCCCCCC)OCC[N+](C)(C)C

InChI

1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1

InChI key

LKQLRGMMMAHREN-YJFXYUILSA-N

description

Sphingomyelin (Brain, Porcine), chloroform

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (860062C-25mg)
pkg of 2 × 4 mL (860062C-200mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

concentration

10 mg/mL (860062C-25mg)
25 mg/mL (860062C-200mg)

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Application

Brain SM may be used:
  • for ion-mobility spectrometry–mass spectrometry (IMS-MS)
  • for lipid mixture in giant unilamellar vesicles
  • as a growth medium for madin-darby canine kidney (MDCK) cells

General description

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.
Sphingomyelin and related lipids

Packaging

5 mL Clear Glass Sealed Ampule (860062C-200mg)
5 mL Clear Glass Sealed Ampule (860062C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system, Liver,Kidney

wgk

WGK 3

法规信息

易制毒化学品（2类）
危险化学品
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历史批次信息供参考:

分析证书(COA)

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Opposing kinesin and myosin-I motors drive membrane deformation and tubulation along engineered cytoskeletal networks
McIntosh B B,et al.
Current Biology, 28(2), 236-248 (2018)
Inhibition of acid sphingomyelinase depletes cellular phosphatidylserine and mislocalizes K-Ras from the plasma membrane
Cho K J,et al.
Molecular and cellular biology, 36(2), 363-374 (2016)
Assessment of altered lipid homeostasis by HILIC-ion mobility-mass spectrometry-based lipidomics
Hines K M, et al.
Journal of Lipid Research, 58(4), 809-819 (2017)
Valerija Vezočnik et al.
Langmuir : the ACS journal of surfaces and colloids, 34(30), 8983-8993 (2018-07-10)
Understanding of the interactions between proteins and natural and artificially prepared lipid membrane surfaces and embedded nonpolar cores is important in studies of physiological processes and their pathologies and is applicable to nanotechnologies. In particular, rapidly growing interest in cellular
Yusuke Sato et al.
Acta biomaterialia, 102, 341-350 (2019-11-17)
Despite the fact that small-sized lipid nanoparticles (LNPs) are important for improved tissue penetration and efficient drug delivery, their poor stability and intracellular trafficking significantly hinders their use as potent small-sized LNPs. It has been reported that both the diffusion
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