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860518P

Avanti

C18 Ceramide (d18:1/18:0)

Avanti Research - A Croda Brand

Synonym(s):

N-stearoyl-D-erythro-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C36H71NO3
CAS Number:
Molecular Weight:
565.95
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860518P-10mg)
pkg of 1 × 5 mg (860518P-5mg)

manufacturer/tradename

Avanti Research - A Croda Brand

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1

InChI key

VODZWWMEJITOND-NXCSZAMKSA-N

General description

C18 Ceramide (d18:1/18:0) synthesis is catalyzed by ceramide synthase (CERS) 1 and 5. It is a component of cellular membrane and has low gel forming ability compared to unsaturated ceramide.

Application

C18 Ceramide (d18:1/18:0) has been used:
  • to induce apoptosis in Manduca embryonic cell line (MRRL-CH1)
  • as a standard to quantify ceramide from liver tissue using liquid chromatography-mass spectrometry
  • to inhibit ceramidase in human embryonic kidney cells (HEK29) with β-glucocerebrosidase (GCase) mutation

Biochem/physiol Actions

C18 Ceramide based derivatives are present in low levels during neurodegeneration. It favors endoplasmic reticulum based stress and autophagy in glioma cells. Low levels of C18-ceramide are implicated in human head and neck squamous cell carcinoma. C18 ceramide may inhibit tumor progression.

Packaging

5 mL Amber Glass Screw Cap Vial (860518P-10mg)
5 mL Amber Glass Screw Cap Vial (860518P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

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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Effect of ceramide structure on membrane biophysical properties: the role of acyl chain length and unsaturation
Pinto SN, et al.
Biochimica et Biophysica Acta - Biomembranes, 1808(11), 2753-2760 (2011)
Overexpression of ceramide synthase 1 increases C18-ceramide and leads to lethal autophagy in human glioma
Koybasi S, et al.
The Journal of biological chemistry, 279(43), 44311-44319 (2004)
Acid ceramidase inhibition ameliorates alpha-synuclein accumulation upon loss of GBA1 function
Kim MJ, et al.
Human Molecular Genetics, 27(11), 1972-1988 (2018)
Hypothalamic AMPK-ER stress-JNK1 axis mediates the central actions of thyroid hormones on energy balance
Martinez-Sanchez N, et al.
Cell Metabolism, 26(1), 212-229 (2017)
Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta
Abeytunga DTU, et al.
Journal of Lipid Research, 45(7), 1221-1231 (2004)

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