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860518P

Avanti

C18 Ceramide (d18:1/18:0)

Avanti Polar Lipids

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Synonym(s):
N-stearoyl-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C36H71NO3
CAS Number:
2304-81-6
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 Polar Lipids

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)

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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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D T U Abeytunga et al.
Journal of lipid research, 45(7), 1221-1231 (2004-04-23)
NMR and electrospray ionization tandem mass spectrometry were used to show for the first time the presence of sphingomyelins in extracts of the tobacco hornworm Manduca sexta (Lepidoptera). The sphingosine in the ceramide was identified as tetradecasphing-4-enine, and the fatty
Overexpression of ceramide synthase 1 increases C18-ceramide and leads to lethal autophagy in human glioma
Wang Z, et al.
Testing, 8(61), 104022-104022 (2017)
Acid ceramidase inhibition ameliorates alpha-synuclein accumulation upon loss of GBA1 function
Kim MJ, et al.
Human Molecular Genetics, 27(11), 1972-1988 (2018)
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)
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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