C16-Ceramide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 565183

CAS#: 4201-58-5

Description: C16-Ceramide is a natural regulatory ligand of p53 in cellular stress.


Price and Availability

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C16-Ceramide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 565183
Name: C16-Ceramide
CAS#: 4201-58-5
Chemical Formula: C34H67NO3
Exact Mass: 537.5121
Molecular Weight: 537.91
Elemental Analysis: C, 75.92; H, 12.56; N, 2.60; O, 8.92


Synonym: C16Ceramide; C16 Ceramide; C16-Ceramide

IUPAC/Chemical Name: N-Palmitoylsphingosine; N-((2S,3R,E)-1,3-Dihydroxyoctadec-4-en-2-yl)palmitamide

InChi Key: YDNKGFDKKRUKPY-OHYPFYFLSA-N

InChi Code: InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27-

SMILES Code: OCC(C(/C=C\CCCCCCCCCCCCC)O)NC(CCCCCCCCCCCCCCC)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934990300


References

1: Schulte-Zweckel J, Schneidewind T, Abad JL, Brockmeyer A, Janning P, Triola G. Azide-tagged sphingolipids for the proteome-wide identification of C16-ceramide-binding proteins. Chem Commun (Camb). 2018 Dec 4;54(97):13742-13745. doi: 10.1039/c8cc05691a. PubMed PMID: 30456403.

2: Kim S, Yang X, Yin A, Zha J, Beharry Z, Bai A, Bielawska A, Bartlett MG, Yin H, Cai H. Dietary palmitate cooperates with Src kinase to promote prostate tumor progression. Prostate. 2019 Mar 22. doi: 10.1002/pros.23796. [Epub ahead of print] PubMed PMID: 30900312.

3: Lu P, White-Gilbertson S, Nganga R, Kester M, Voelkel-Johnson C. Expression of the SNAI2 transcriptional repressor is regulated by C(16)-ceramide. Cancer Biol Ther. 2019 Mar 5:1-9. doi: 10.1080/15384047.2019.1579962. [Epub ahead of print] PubMed PMID: 30836822.

4: Yeganeh B, Lee J, Bilodeau C, Lok I, Ermini L, Ackerley C, Caniggia I, Tibboel J, Kroon A, Post M. Acid Sphingomyelinase Inhibition Attenuates Cell Death in Mechanically Ventilated Newborn Rat Lung. Am J Respir Crit Care Med. 2019 Mar 15;199(6):760-772. doi: 10.1164/rccm.201803-0583OC. PubMed PMID: 30326731.

5: Fekry B, Jeffries KA, Esmaeilniakooshkghazi A, Szulc ZM, Knagge KJ, Kirchner DR, Horita DA, Krupenko SA, Krupenko NI. C(16)-ceramide is a natural regulatory ligand of p53 in cellular stress response. Nat Commun. 2018 Oct 8;9(1):4149. doi: 10.1038/s41467-018-06650-y. PubMed PMID: 30297838; PubMed Central PMCID: PMC6175828.

6: Holmes RS, Barron KA, Krupenko NI. Ceramide Synthase 6: Comparative Analysis, Phylogeny and Evolution. Biomolecules. 2018 Oct 8;8(4). pii: E111. doi: 10.3390/biom8040111. PubMed PMID: 30297675; PubMed Central PMCID: PMC6315813.

7: Speirs MMP, Swensen AC, Chan TY, Jones PM, Holman JC, Harris MB, Maschek JA, Cox JE, Carson RH, Hill JT, Andersen JL, Prince JT, Price JC. Imbalanced sphingolipid signaling is maintained as a core proponent of a cancerous phenotype in spite of metabolic pressure and epigenetic drift. Oncotarget. 2019 Jan 11;10(4):449-479. doi: 10.18632/oncotarget.26533. eCollection 2019 Jan 11. PubMed PMID: 30728898; PubMed Central PMCID: PMC6355186.

8: Kim MH, Park JW, Lee EJ, Kim S, Shin SH, Ahn JH, Jung Y, Park I, Park WJ. C16 ceramide and sphingosine 1 phosphate/S1PR2 have opposite effects on cell growth through mTOR signaling pathway regulation. Oncol Rep. 2018 Nov;40(5):2977-2987. doi: 10.3892/or.2018.6689. Epub 2018 Sep 7. PubMed PMID: 30226616.

9: Tidhar R, Zelnik ID, Volpert G, Ben-Dor S, Kelly S, Merrill AH Jr, Futerman AH. Eleven residues determine the acyl chain specificity of ceramide synthases. J Biol Chem. 2018 Jun 22;293(25):9912-9921. doi: 10.1074/jbc.RA118.001936. Epub 2018 Apr 9. PubMed PMID: 29632068; PubMed Central PMCID: PMC6016465.

10: Zhong L, Kong JN, Dinkins MB, Leanhart S, Zhu Z, Spassieva SD, Qin H, Lin HP, Elsherbini A, Wang R, Jiang X, Nikolova-Karakashian M, Wang G, Bieberich E. Increased liver tumor formation in neutral sphingomyelinase-2-deficient mice. J Lipid Res. 2018 May;59(5):795-804. doi: 10.1194/jlr.M080879. Epub 2018 Mar 22. PubMed PMID: 29567647; PubMed Central PMCID: PMC5928441.

11: Meher AK, Spinosa M, Davis JP, Pope N, Laubach VE, Su G, Serbulea V, Leitinger N, Ailawadi G, Upchurch GR Jr. Novel Role of IL (Interleukin)-1β in Neutrophil Extracellular Trap Formation and Abdominal Aortic Aneurysms. Arterioscler Thromb Vasc Biol. 2018 Apr;38(4):843-853. doi: 10.1161/ATVBAHA.117.309897. Epub 2018 Feb 22. PubMed PMID: 29472233; PubMed Central PMCID: PMC5864548.

12: Helke K, Angel P, Lu P, Garrett-Mayer E, Ogretmen B, Drake R, Voelkel-Johnson C. Ceramide Synthase 6 Deficiency Enhances Inflammation in the DSS model of Colitis. Sci Rep. 2018 Jan 26;8(1):1627. doi: 10.1038/s41598-018-20102-z. PubMed PMID: 29374263; PubMed Central PMCID: PMC5786068.

13: Scheffel MJ, Helke K, Lu P, Bowers JS, Ogretmen B, Garrett-Mayer E, Paulos CM, Voelkel-Johnson C. Adoptive Transfer of Ceramide Synthase 6 Deficient Splenocytes Reduces the Development of Colitis. Sci Rep. 2017 Nov 14;7(1):15552. doi: 10.1038/s41598-017-15791-x. PubMed PMID: 29138469; PubMed Central PMCID: PMC5686186.

14: Hassouneh LK, Timofiychuk OA, Babenko NA. Acid sphingomyelinase inhibitors, imipramine and zoledronic acid, increase skeletal muscle tissue sensitivity to insulin action at old age. Gen Physiol Biophys. 2018 Mar;37(2):163-174. doi: 10.4149/gpb_2017020. Epub 2017 Nov 10. PubMed PMID: 29125130.

15: Blaess M, Bibak N, Claus RA, Kohl M, Bonaterra GA, Kinscherf R, Laufer S, Deigner HP. NB 06: From a simple lysosomotropic aSMase inhibitor to tools for elucidating the role of lysosomes in signaling apoptosis and LPS-induced inflammation. Eur J Med Chem. 2018 Jun 10;153:73-104. doi: 10.1016/j.ejmech.2017.09.021. Epub 2017 Sep 21. PubMed PMID: 29031494.

16: Stöckli J, Fisher-Wellman KH, Chaudhuri R, Zeng XY, Fazakerley DJ, Meoli CC, Thomas KC, Hoffman NJ, Mangiafico SP, Xirouchaki CE, Yang CH, Ilkayeva O, Wong K, Cooney GJ, Andrikopoulos S, Muoio DM, James DE. Metabolomic analysis of insulin resistance across different mouse strains and diets. J Biol Chem. 2017 Nov 24;292(47):19135-19145. doi: 10.1074/jbc.M117.818351. Epub 2017 Oct 5. PubMed PMID: 28982973; PubMed Central PMCID: PMC5702658.