C8 Ceramide
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 563684

CAS#: 74713-59-0

Description: C8 Ceramide is a cell-permeable analog of naturally occurring ceramides.


Price and Availability

Size
Price

1mg
USD 190
Size
Price

5mg
USD 340
Size
Price

10mg
USD 530

C8 Ceramide, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 563684
Name: C8 Ceramide
CAS#: 74713-59-0
Chemical Formula: C26H51NO3
Exact Mass: 425.3869
Molecular Weight: 425.69
Elemental Analysis: C, 73.36; H, 12.08; N, 3.29; O, 11.27


Synonym: C8 Ceramide; C8-Ceramide; N-Octanoyl-D-erythro-Sphingosine;

IUPAC/Chemical Name: N-[(E,2S,3R)-1,3-Dihydroxyoctadec-4-en-2-yl]octanamide

InChi Key: APDLCSPGWPLYEQ-WRBRXSDHSA-N

InChi Code: InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1

SMILES Code: CCCCCCCC(N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO)=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:
2934.99.03.00


References

1: Lv H, Zhang Z, Wu X, Wang Y, Li C, Gong W, Gui L, Wang X. Preclinical Evaluation of Liposomal C8 Ceramide as a Potent anti-Hepatocellular Carcinoma Agent. PLoS One. 2016 Jan 4;11(1):e0145195. doi: 10.1371/journal.pone.0145195. eCollection 2016. PubMed PMID: 26727592; PubMed Central PMCID: PMC4699687.

2: Barui S, Saha S, Yakati V, Chaudhuri A. Systemic Codelivery of a Homoserine Derived Ceramide Analogue and Curcumin to Tumor Vasculature Inhibits Mouse Tumor Growth. Mol Pharm. 2016 Feb 1;13(2):404-19. doi: 10.1021/acs.molpharmaceut.5b00644. Epub 2016 Jan 15. PubMed PMID: 26716471.

3: Liu H, Yang J, Wang Y, Wei Y, Cao J, Lu Y. [Effect of C8-ceramide on apoptosis of alveolar type II epithelial cells]. Zhonghua Jie He He Hu Xi Za Zhi. 2015 Jun;38(6):445-50. Chinese. PubMed PMID: 26702858.

4: Guo L, Tan G, Liu P, Li H, Tang L, Huang L, Ren Q. Three plasma metabolite signatures for diagnosing high altitude pulmonary edema. Sci Rep. 2015 Oct 13;5:15126. doi: 10.1038/srep15126. PubMed PMID: 26459926; PubMed Central PMCID: PMC4602305.

5: Pritzl CJ, Seo YJ, Xia C, Vijayan M, Stokes ZD, Hahm B. A ceramide analogue stimulates dendritic cells to promote T cell responses upon virus infections. J Immunol. 2015 May 1;194(9):4339-49. doi: 10.4049/jimmunol.1402672. Epub 2015 Mar 25. PubMed PMID: 25810392; PubMed Central PMCID: PMC4402267.

6: Zhang C, Guo L, Zhu B, Feng Y, Yu S, An N, Wang X. Effects of 3, 5, 3'-triiodothyronine (t3) and follicle stimulating hormone on apoptosis and proliferation of rat ovarian granulosa cells. Chin J Physiol. 2013 Oct 31;56(5):298-305. doi: 10.4077/CJP.2013.BAB186. Epub 2013 Aug 31. PubMed PMID: 24032715.

7: Jung JS, Shin KO, Lee YM, Shin JA, Park EM, Jeong J, Kim DH, Choi JW, Kim HS. Anti-inflammatory mechanism of exogenous C2 ceramide in lipopolysaccharide-stimulated microglia. Biochim Biophys Acta. 2013 Jun;1831(6):1016-26. doi: 10.1016/j.bbalip.2013.01.020. Epub 2013 Feb 4. PubMed PMID: 23384839.

8: Kue CS, Lim HX, Jung MY, Hong HJ, Cho D, Kim TS. C6-ceramide in combination with transforming growth factor-β enhances Treg cell differentiation and stable FoxP3 expression in vitro and in vivo. Immunobiology. 2013 Jul;218(7):952-9. doi: 10.1016/j.imbio.2012.11.003. Epub 2012 Nov 21. PubMed PMID: 23313049.

9: Singh AT, Dharmarajan A, Aye IL, Keelan JA. Ceramide biosynthesis and metabolism in trophoblast syncytialization. Mol Cell Endocrinol. 2012 Oct 15;362(1-2):48-59. doi: 10.1016/j.mce.2012.05.009. Epub 2012 May 28. PubMed PMID: 22652149.

10: Gusain A, Hatcher JF, Adibhatla RM, Wesley UV, Dempsey RJ. Anti-proliferative effects of tricyclodecan-9-yl-xanthogenate (D609) involve ceramide and cell cycle inhibition. Mol Neurobiol. 2012 Jun;45(3):455-64. doi: 10.1007/s12035-012-8254-0. Epub 2012 Mar 14. Erratum in: Mol Neurobiol. 2012 Jun;45(3):465. PubMed PMID: 22415444; PubMed Central PMCID: PMC3381991.

11: Camgoz A, Gencer EB, Ural AU, Avcu F, Baran Y. Roles of ceramide synthase and ceramide clearence genes in nilotinib-induced cell death in chronic myeloid leukemia cells. Leuk Lymphoma. 2011 Aug;52(8):1574-84. doi: 10.3109/10428194.2011.568653. PubMed PMID: 21756066.

12: Kartal M, Saydam G, Sahin F, Baran Y. Resveratrol triggers apoptosis through regulating ceramide metabolizing genes in human K562 chronic myeloid leukemia cells. Nutr Cancer. 2011;63(4):637-44. doi: 10.1080/01635581.2011.538485. PubMed PMID: 21500096.

13: Gencer EB, Ural AU, Avcu F, Baran Y. A novel mechanism of dasatinib-induced apoptosis in chronic myeloid leukemia; ceramide synthase and ceramide clearance genes. Ann Hematol. 2011 Nov;90(11):1265-75. doi: 10.1007/s00277-011-1212-5. Epub 2011 Apr 1. PubMed PMID: 21455605.

14: Zheng T, Li W, Altura BT, Shah NC, Altura BM. Sphingolipids regulate [Mg2+]o uptake and [Mg2+]i content in vascular smooth muscle cells: potential mechanisms and importance to membrane transport of Mg2+. Am J Physiol Heart Circ Physiol. 2011 Feb;300(2):H486-92. doi: 10.1152/ajpheart.00976.2010. Epub 2010 Nov 26. PubMed PMID: 21112948; PubMed Central PMCID: PMC3044054.

15: Józefowski S, Czerkies M, Łukasik A, Bielawska A, Bielawski J, Kwiatkowska K, Sobota A. Ceramide and ceramide 1-phosphate are negative regulators of TNF-α production induced by lipopolysaccharide. J Immunol. 2010 Dec 1;185(11):6960-73. doi: 10.4049/jimmunol.0902926. Epub 2010 Nov 1. PubMed PMID: 21041721.

16: Cakir Z, Saydam G, Sahin F, Baran Y. The roles of bioactive sphingolipids in resveratrol-induced apoptosis in HL60: acute myeloid leukemia cells. J Cancer Res Clin Oncol. 2011 Feb;137(2):279-86. doi: 10.1007/s00432-010-0884-x. Epub 2010 Apr 18. PubMed PMID: 20401667.

17: Antoon JW, Liu J, Gestaut MM, Burow ME, Beckman BS, Foroozesh M. Design, synthesis, and biological activity of a family of novel ceramide analogues in chemoresistant breast cancer cells. J Med Chem. 2009 Sep 24;52(18):5748-52. doi: 10.1021/jm9009668. PubMed PMID: 19694470.

18: Gouazé-Andersson V, Yu JY, Kreitenberg AJ, Bielawska A, Giuliano AE, Cabot MC. Ceramide and glucosylceramide upregulate expression of the multidrug resistance gene MDR1 in cancer cells. Biochim Biophys Acta. 2007 Dec;1771(12):1407-17. Epub 2007 Nov 9. PubMed PMID: 18035065; PubMed Central PMCID: PMC3569095.

19: Chiba N, Masuda A, Yoshikai Y, Matsuguchi T. Ceramide inhibits LPS-induced production of IL-5, IL-10, and IL-13 from mast cells. J Cell Physiol. 2007 Oct;213(1):126-36. PubMed PMID: 17458900.

20: Turzanski J, Grundy M, Shang S, Russell N, Pallis M. P-glycoprotein is implicated in the inhibition of ceramide-induced apoptosis in TF-1 acute myeloid leukemia cells by modulation of the glucosylceramide synthase pathway. Exp Hematol. 2005 Jan;33(1):62-72. PubMed PMID: 15661399.