C16 Sphingomyelin (d18:1/16:0) (CAS 6254-89-3) | Cayman Chemical
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C16 Sphingomyelin (d18:1/16:0)

Item № 10007946
CAS № 6254-89-3
Purity ≥98%
product image
                (CAS 6254-89-3)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $56.00 0.00
     5 mg $252.00 0.00
     10 mg $448.00 0.00

Pricing updated 2018-07-16. Prices are subject to change without notice.

Description
Synonyms
  • Palmitoyl Sphingomyelin
  • N-Palmitoyl-D-erythro-Sphingosylphosphorylcholine
  • SM(d18:1/16:0)
  • Sphingomyelin (d18:1/16:0)

Sphingomyelins are complex membrane lipids composed of phosphorylcholine, sphingosine, and an acylated group, such as a fatty acid. C16 Sphingomyelin is a form of sphingomyelin containing palmitate (16:0) at the variable acylation position. It is the most common form of sphingomyelin found in eggs and is less abundant in the brain and milk. C16 Sphingomyelin interacts with cholesterol in ordered lipid domains (lipid rafts).1,2 Sphingomyelinases remove phosphorylcholine from C16 sphingomyelin to produce C16 ceramide. While ceramides commonly induce apoptosis, ceramides with different fatty acid chain lengths might direct distinct functions and, in some cases, reduce apoptosis.3,4,5

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Technical Information
Formal Name
4-hydroxy-7S-[1R-hydroxy-2E-hexadecenyl]-N,N,N-trimethyl-9-oxo-4-oxide-3,5-dioxa-8-aza-4-phosphatetracosan-1-aminium
CAS Number
6254-89-3
Synonyms
  • Palmitoyl Sphingomyelin
  • N-Palmitoyl-D-erythro-Sphingosylphosphorylcholine
  • SM(d18:1/16:0)
  • Sphingomyelin (d18:1/16:0)
Molecular Formula
C39H79N2O6P
Formula Weight
703.0
Purity
≥98%
Formulation
A crystalline solid
SMILES
CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](NC(CCCCCCCCCCCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O
InChI Code
InChI=1S/C39H79N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h30,32,37-38,42H,6-29,31,33-36H2,1-5H3,(H-,40,43,44,45)/b32-30+/t37-,38+/m0/s1
InChI Key
RWKUXQNLWDTSLO-GWQJGLRPSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
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References & Product Citations
Product Description References

1. Megha, Sawatzki, P., Kolter, T., et al. Effect of ceramide N-acyl chain and polar headgroup structure on the properties of ordered lipid domains (lipid rafts). Biochimica et Biophysica Acta 1768(9), 2205-2212 (2007).

2. Quinn, P.J., and Wolf, C. Egg-sphingomyelin and cholesterol form a stoichiometric molecular complex in bilayers of egg-phosphatidylcholine. J. Phys .Chem. B 114(47), 15536-15545 (2010).

3. Ruvolo, P.P. Intracellular signal transduction pathways activated by ceramide and its metabolites. Pharmacol. Res. 47(5), 383-392 (2003).

4. White-Gilbertson, S., Mullen, T., Senkal, C., et al. Ceramide synthase 6 modulates TRAIL sensitivity and nuclear translocation of active caspase 3 in colon cancer cells. Oncogene 28(8), 1132-1141 (2009).

5. Senkal, C.E., Ponnusamy, S., Bielawski, J., et al. Antiapoptotic roles of ceramide-synthase-6-generated C16-ceramide via selective regulation of the ATF6/CHOP arm of ER-stress-response pathways. FASEB J. 24(1), 296-308 (2010).

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