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860514P

Avanti

C14 Ceramide (d18:1/14:0)

Avanti Polar Lipids 860514P, powder

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Synonym(s):
N-myristoyl-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C32H63NO3
CAS Number:
123408-74-2
Molecular Weight:
509.85
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 25 mg (860514P-25mg)
pkg of 1 × 5 mg (860514P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860514P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C32H63NO3/c1-3-5-7-9-11-13-15-16-18-19-21-23-25-27-31(35)30(29-34)33-32(36)28-26-24-22-20-17-14-12-10-8-6-4-2/h25,27,30-31,34-35H,3-24,26,28-29H2,1-2H3,(H,33,36)/b27-25+/t30-,31+/m0/s1

InChI key

ZKRPGPZHULJLKJ-JHRQRACZSA-N

General description

Ceramide synthesis is majorly driven by de novo pathway involving the palmitoyl-CoA and L-serine, and also by salvage pathway via recycling of complex sphingolipids. The ceramide transporter, Cert mediates the transfer of C14 from smooth endoplasmic reticulum to Golgi. Ceramide synthase CerS6 enzyme is involved in the synthesis of C14 ceramide.

Application

C14 Ceramide (d18:1/14:0) is suitable for use
  • as a standard in high-performance liquid chromatography/tandem mass spectrometry (LC/MS2) for ceramide quantification from muscel biopsies
  • in lipid monolayer preparation for biophysical studies
  • in the morphological and dimensional evaluation studies

Biochem/physiol Actions

Ceramides regulate biological processes including proliferation, differentiation and apoptosis. In the cystic fibrosis patients, elevated levels of C14 ceramide is observed. It is also a potential biomarker for hepatic steatosis (HS) and C14 ceramide levels correlate with the aspartate aminotransferase (AST) / alanine transaminase (ALT) ratio. Tumor necrosis factor α (TNFα) mediates increase in the C14 levels. Fumonisin B1 prevents the C14 accumulation.

Packaging

5 mL Amber Glass Screw Cap Vial (860514P-25mg)
5 mL Amber Glass Screw Cap Vial (860514P-5mg)

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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Biochemistry of very-long-chain and long-chain ceramides in cystic fibrosis and other diseases: The importance of side chain
Garic D, et al.
Progress in Lipid Research (2019)
Ceramide N-acyl chain length: a determinant of bidimensional transitions, condensed domain morphology, and interfacial thickness
Dupuy F, et al.
Langmuir, 27(7), 3783-3791 (2011)
Tumor necrosis factor-alpha(TNFalpha)-induced ceramide generation via ceramide synthases regulates loss of focal adhesion kinase (FAK) and programmed cell death
Hernandez-Corbacho M, et al.
The Journal of Biological Chemistry, 290(42), 25356-25373 (2015)
Association between Plasmatic Ceramides Profile and AST/ALT Ratio: C14: 0 Ceramide as Predictor of Hepatic Steatosis in Adolescents Independently of Obesity
Maldonado-Hernandez J, et al.
Canadian journal of gastroenterology & hepatology, 2017 (2017)
Ceramide effects in the bicelle structure
Barbosa-Barros L, et al.
Colloids and Surfaces. A, Physicochemical and Engineering Aspects, 317(1-3), 576-584 (2008)
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