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860517P

Avanti

C17 Ceramide (d18:1/17:0)

Avanti Research™ - A Croda Brand

Synonym(s):

N-heptadecanoyl-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C35H69NO3
CAS Number:
67492-16-4
Molecular Weight:
551.93
MDL number:
MFCD02259275
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

C17 Ceramide (d18:1/17:0), Avanti Research™ - A Croda Brand

SMILES string

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

InChI

1S/C35H69NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-35(39)36-33(32-37)34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h28,30,33-34,37-38H,3-27,29,31-32H2,1-2H3,(H,36,39)/b30-28+/t33-,34+/m0/s1

InChI key

ICWGMOFDULMCFL-QKSCFGQVSA-N

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 10 mg (860517P-10mg)
pkg of 1 × 25 mg (860517P-25mg)
pkg of 1 × 5 mg (860517P-5mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

Application

C17 Ceramide (d18:1/17:0) has been used:
  • as an internal standard for myocardial ceramide quantification using chromatography with negative ion electrospray ionization coupled to tandem mass spectrometry
  • as an internal standard in tandem mass spectrometry (MS/MS)
  • as a substrate for sphingomyelin synthase 2 enzyme

Biochem/physiol Actions

Ceramides play a key role in regulating various cellular processes like senescence and apoptosis. They are directly involved in the proliferation and differentiation of skin cells and regulate skin barrier functionality. Ceramide based analogs are potential anti-tumor agents and are regarded as tumor suppressor lipid.

General description

Ceramide synthesis is mediated either by the salvage pathway by the acylation of sphingosine or sphingolipids hydrolysis or by de novo pathway via dihydroceramide formation. Structurally, ceramides have a sphingoid base, a long-chain amino alcohol linked to fatty acid by an amide bond.

Packaging

5 mL Amber Glass Screw Cap Vial (860517P-10mg)
5 mL Amber Glass Screw Cap Vial (860517P-25mg)
5 mL Amber Glass Screw Cap Vial (860517P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk

WGK 3

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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)
Ye-Ryung Kim et al.
Experimental & molecular medicine, 51(11), 129-129 (2019-11-05)
The endoplasmic reticulum (ER) is not only important for protein synthesis and folding but is also crucial for lipid synthesis and metabolism. In the current study, we demonstrate an important role of ceramide synthases (CerS) in ER stress and NAFLD
Takuya Takeichi et al.
The Journal of clinical investigation, 130(2), 890-903 (2019-11-02)
The corneocyte lipid envelope, composed of covalently bound ceramides and fatty acids, is important to the integrity of the permeability barrier in the stratum corneum, and its absence is a prime structural defect in various skin diseases associated with defective
Long-term high-fat diet-induced obesity decreases the cardiac leptin receptor without apparent lipotoxicity
Nascimento AF, et al.
Life Sciences, 88(23-24), 1031-1038 (2011)
Alexander Triebl et al.
Journal of lipid research, 61(1), 105-115 (2019-11-17)
Quantitative MS of human plasma lipids is a promising technology for translation into clinical applications. Current MS-based lipidomic methods rely on either direct infusion (DI) or chromatographic lipid separation methods (including reversed phase and hydrophilic interaction LC). However, the use
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