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860061C

Avanti

Egg SM

Avanti Research™ - A Croda Brand

Synonym(s):

16:0 SM; Hexadecanoyl Sphingomyelin; N-hexadecanoyl-D-erythro-sphingosylphosphorylcholine; N-(hexadecanoyl)-sphing-4-enine-1-phosphocholine

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About This Item

CAS Number:
383907-87-7
UNSPSC Code:
12352211
NACRES:
NA.25

description

Sphingomyelin (Egg, Chicken), chloroform

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (860061C-25mg)
pkg of 2 × 20 mL (860061C-1g)
pkg of 2 × 4 mL (860061C-200mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

concentration

10 mg/mL (860061C-25mg)
25 mg/mL (860061C-1g)
25 mg/mL (860061C-200mg)

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1

InChI key

RWKUXQNLWDTSLO-GWQJGLRPSA-N

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

Application

Egg SM is suitable for use:
  • for preparation of liposomes
  • for synthesizing dihydrosphingomyelin (dhSM)
  • for sphingomyelin assay

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (860061C-1g)
5 mL Clear Glass Sealed Ampule (860061C-200mg)
5 mL Clear Glass Sealed Ampule (860061C-25mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

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

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

does not flash

Flash Point(C)

does not flash

Regulatory Information

易制毒化学品（2类）
危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Light Scattering By Optically-Trapped Vesicles Affords Unprecedented Temporal Resolution Of Lipid-Raft Dynamics
Collard L, et al.
Scientific reports, 7(1), 8589-8589 (2017)
Maia Kinnebrew et al.
eLife, 8 (2019-10-29)
Previously we proposed that transmission of the hedgehog signal across the plasma membrane by Smoothened is triggered by its interaction with cholesterol (Luchetti et al., 2016). But how is cholesterol, an abundant lipid, regulated tightly enough to control a signaling
A novel flow cytometric assay to quantify interactions between proteins and membrane lipids
Temmerman K and Nickel W
Journal of Lipid Research, 50(6), 1245-1254 (2009)
Dihydroceramide accumulation mediates cytotoxic autophagy of cancer cells via autolysosome destabilization
Hernandez-Tiedra S, et al.
Autophagy, 12(11), 2213-2229 (2016)
Changes in serum sphingomyelin after Roux-en-Y gastric bypass surgery are related to diabetes status
Carlsson ER, et al.
Frontiers in Endocrinology, 9, 172-172 (2018)
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