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860516P

Avanti

C16 Ceramide (d18:1/16:0)

Avanti Research - A Croda Brand

Synonym(s):

N-palmitoyl-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C34H67NO3
CAS Number:
Molecular Weight:
537.90
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860516P-10mg)
pkg of 1 × 100 mg (860516P-100mg)
pkg of 1 × 25 mg (860516P-25mg)
pkg of 1 × 5 mg (860516P-5mg)
pkg of 1 × 50 mg (860516P-50mg)

manufacturer/tradename

Avanti Research - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

OC[C@]([H])(NC(CCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

InChI

1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1

InChI key

YDNKGFDKKRUKPY-TURZORIXSA-N

General description

Ceramide comprise sphingosine and fatty acid and belongs to the sphingolipids family.

Application

C16 Ceramide (d18:1/16:0) has been used:
  • as an internal standard in the chromatography with negative ion electrospray ionization coupled to tandem mass spectrometry for myocardial ceramide quantification
  • as an internal standard for the ceramide quantification from rat samples using liquid chromatography-mass spectrometry
  • to test its effect on mitochondrial stress response in worms

Biochem/physiol Actions

C16 Ceramide levels are elevated in chronic alcohol-related liver disease (ALD). In general, ceramide inhibits mitochondrial function and insulin signaling. They are essential component of cell membrane and are involved in lipid raft formation. C16 ceramide based analog (C2-C16 CCPS) is potential anticancer agent used in chemotherapy. The levels of C16 ceramide and its ratio with other ceramides is regarded as a biomarker in predicting coronary artery disease (CAD). It interacts with the DNA-binding domain of tumor suppressor protein p53 and activates p53.

Packaging

5 mL Amber Glass Screw Cap Vial (860516P-100mg)
5 mL Amber Glass Screw Cap Vial (860516P-10mg)
5 mL Amber Glass Screw Cap Vial (860516P-25mg)
5 mL Amber Glass Screw Cap Vial (860516P-50mg)
5 mL Amber Glass Screw Cap Vial (860516P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

also commonly purchased with this product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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M Laura Fanani et al.
Langmuir : the ACS journal of surfaces and colloids, 34(39), 11749-11758 (2018-09-06)
Sphingosine [(2 S,3 R,4 E)-2-amino-4-octadecene-1,3-diol] is the most common sphingoid base in mammals. Ceramides are N-acyl sphingosines. Numerous small variations on this canonical structure are known, including the 1-deoxy, the 4,5-dihydro, and many others. However, whenever there is a Δ4
Aritz B García-Arribas et al.
Langmuir : the ACS journal of surfaces and colloids, 32(35), 9053-9063 (2016-08-04)
The effects of increasing amounts of palmitoylceramide (pCer) on human red blood cell lipid membranes have been studied using atomic force microscopy of supported lipid bilayers, in both imaging (bilayer thickness) and force-spectroscopy (nanomechanical resistance) modes. Membranes appeared homogeneous with
Insulin resistance, ceramide accumulation, and endoplasmic reticulum stress in human chronic alcohol-related liver disease
Longato L, et al.
Oxidative Medicine and Cellular Longevity, 2012 (2012)
Development and validation of a high-throughput LC-MS/MS assay for routine measurement of molecular ceramides
Kauhanen D, et al.
Analytical and Bioanalytical Chemistry, 408(13), 3475-3483 (2016)
Meenu N Perera et al.
Chemistry and physics of lipids, 194, 110-116 (2015-09-27)
A ceramide commonly found in mammalian cells, C16-ceramide (N-palmitoyl-d-erythro-sphingosine), is capable of forming large, protein-permeable channels in the mitochondrial outer membrane (MOM). However, C16-ceramide is unable to permeabilize the plasma membrane of erythrocytes. This specificity is unexpected considering that ceramide

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