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860506P

Avanti

C6 Ceramide (d18:1/6:0)

Avanti Polar Lipids

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Synonym(s):
N-hexanoyl-D-erythro-sphingosine
Empirical Formula (Hill Notation):
C24H47NO3
CAS Number:
124753-97-5
Molecular Weight:
397.63
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860506P-10mg)
pkg of 1 × 5 mg (860506P-5mg)

manufacturer/tradename

Avanti Polar Lipids

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+

InChI key

NPRJSFWNFTXXQC-VHEBQXMUSA-N

General description

C6 Ceramide (d18:1/6:0) is a short chain and a cell permeable ceramide. It comprises amino alcoholic chain attached to fatty acyl chain via an amide linkage.

Application

C6 Ceramide (d18:1/6:0) has been used as a chemotherapeutic agent to test its anti-tumor effect in breast cancer cells and ovarian cancer cell lines. It has also been used to test chemo-sensitization effects in cancer cells.

Biochem/physiol Actions

C6 Ceramide (d18:1/6:0) is involved in inhibiting proliferation and inducing apoptosis. When used in combination with acid ceramidase inhibitor DM102, [(2R,3Z)-N-(1-hydroxyoctadec-3-en-2-yl)pivaloylamide], it favors cell death in human breast cancer cells lines. C6 Ceramide may serve as an adjunct in chemotherapy. It elicits anti-tumor effects via AKT (serine/threonine-specific protein kinase) dephosphorylation and α-tubulin acetylation.

Packaging

5 mL Amber Glass Screw Cap Vial (860506P-10mg)
5 mL Amber Glass Screw Cap Vial (860506P-5mg)

also commonly purchased with this product

Product No.
Description
Pricing

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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C6-ceramide and targeted inhibition of acid ceramidase induce synergistic decreases in breast cancer cell growth
Flowers M, et al.
Breast Cancer Research and Treatment, 133(2), 447-458 (2012)
Mechanisms involved in exogenous C2-and C6-ceramide-induced cancer cell toxicity
Fillet M, et al.
Biochemical Pharmacology, 65(10), 1633-1642 (2003)
C Ji et al.
Oncogene, 29(50), 6557-6568 (2010-08-31)
New chemotherapy-enhancing strategies are needed for better cancer therapy. Previous studies suggest that exogenous cell-permeable C6 ceramide may be a useful adjunct to the anti-tumor effects of chemotherapeutic agents (such as Taxol) against multiple cancers. Here we demonstrate that exogenous
Short-chain C6 ceramide sensitizes AT406-induced anti-pancreatic cancer cell activity
Zhao X, et al.
Biochemical and Biophysical Research Communications, 479(2), 166-172 (2016)
C6 ceramide dramatically enhances docetaxel-induced growth inhibition and apoptosis in cultured breast cancer cells: a mechanism study
Yang L, et al.
Experimental Cell Research, 332(1), 47-59 (2015)
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