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810218C

Avanti

C6-NBD Sphingomyelin

Avanti Polar Lipids 810218C

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Synonym(s):
N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-sphingosine-1-phosphocholine
Empirical Formula (Hill Notation):
C35H61N6O9P
CAS Number:
94885-04-8
Molecular Weight:
740.87
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (810218C-1mg)

manufacturer/tradename

Avanti Polar Lipids 810218C

concentration

1 mg/mL (810218C-1mg)

shipped in

dry ice

storage temp.

−20°C

InChI

1S/C35H61N6O9P/c1-5-6-7-8-9-10-11-12-13-14-15-16-18-21-32(42)30(28-49-51(46,47)48-27-26-41(2,3)4)37-33(43)22-19-17-20-25-36-29-23-24-31(40(44)45)35-34(29)38-50-39-35/h18,21,23-24,30,32,42H,5-17,19-20,22,25-28H2,1-4H3,(H2-,36,37,39,43,46,47)/b21-18+/t30-,32+/m0/s1

InChI key

YDBDYTGWMRUUSN-PERJAUJZSA-N

General description

C6-NBD Sphingomyelin is a fluorescent derivative of sphingomyelin. Its fluorescent property is due to presence of NBD (2-(4-nitro-2,1,3-benzoxadiazol-7-yl) aminoethyl) group. Sphingomyelin is generally concentrated in the outer leaflet of the plasma membrane.

Application

C6-NBD Sphingomyelin is suitable to study sphingomyelin endocytosis using fluorescence microscopy.

Biochem/physiol Actions

Sphingomyelin (SM) is involved in signal transduction and membrane trafficking. It is synthesized by the transfer of phosphocholine from phosphatidylcholine onto ceramide, catalysed by sphingomyelin synthase on the cell surface and in lumen of the Golgi. SM has high packing density and affinity for sterol which offer a strong barrier to extracellular environment.

Packaging

5 mL Amber Glass Screw Cap Vial (810218C-1mg)

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

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

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Fluorescent and Luminescent Probes for Biological Activity (1999)
mTOR complex 1 activity is required to maintain the canonical endocytic recycling pathway against lysosomal delivery
Dauner K, et al.
The Journal of biological chemistry, 292(14), 5737-5747 (2017)
Mark L Schultz et al.
BMC medicine, 17(1), 200-200 (2019-11-13)
Niemann-Pick disease type C is a fatal and progressive neurodegenerative disorder characterized by the accumulation of unesterified cholesterol in late endosomes and lysosomes. We sought to develop new therapeutics for this disorder by harnessing the body's endogenous cholesterol scavenging particle
Kristin Dauner et al.
The Journal of biological chemistry, 292(14), 5737-5747 (2017-02-16)
The plasma membrane of mammalian cells undergoes constitutive endocytosis, endocytic sorting, and recycling, which delivers nutrients to the lysosomes. The receptors, along with membrane lipids, are normally returned to the plasma membrane to sustain this action. It is not known
Klazien Huitema et al.
The EMBO journal, 23(1), 33-44 (2003-12-20)
Sphingomyelin (SM) is a major component of animal plasma membranes. Its production involves the transfer of phosphocholine from phosphatidylcholine onto ceramide, yielding diacylglycerol as a side product. This reaction is catalysed by SM synthase, an enzyme whose biological potential can
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