MedKoo Cat#: 598937 | Name: Ceramide 1 A

Description:

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

Ceramide 1 A is a waxy lipid molecule.

Chemical Structure

Ceramide 1 A
Ceramide 1 A
CAS#179186-48-2

Theoretical Analysis

MedKoo Cat#: 598937

Name: Ceramide 1 A

CAS#: 179186-48-2

Chemical Formula: C63H121NO6

Exact Mass: 987.9194

Molecular Weight: 988.66

Elemental Analysis: C, 76.54; H, 12.34; N, 1.42; O, 9.71

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Ceramide 1 A; Linoleoyloxyheptacosanoyl-C18-phytosphingosine;
IUPAC/Chemical Name
27-oxo-27-(((2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl)amino)heptacosyl (9Z,12Z)-octadeca-9,12-dienoate
InChi Key
RBBHGNBWKGCPAF-XEKXCHJCSA-N
InChi Code
InChI=1S/C63H121NO6/c1-3-5-7-9-11-13-15-17-28-32-36-40-44-48-52-56-62(68)70-57-53-49-45-41-37-33-30-27-25-23-21-19-18-20-22-24-26-29-31-35-39-43-47-51-55-61(67)64-59(58-65)63(69)60(66)54-50-46-42-38-34-16-14-12-10-8-6-4-2/h11,13,17,28,59-60,63,65-66,69H,3-10,12,14-16,18-27,29-58H2,1-2H3,(H,64,67)/b13-11-,28-17-/t59-,60+,63-/m0/s1
SMILES Code
CCCCC/C=C\C/C=C\CCCCCCCC(OCCCCCCCCCCCCCCCCCCCCCCCCCCC(N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC)=O)=O
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).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 988.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Niino S, Nakamura Y, Hirabayashi Y, Nagano-Ito M, Ichikawa S. A small molecule inhibitor of Bcl-2, HA14-1, also inhibits ceramide glucosyltransferase. Biochem Biophys Res Commun. 2013 Apr 5;433(2):170-4. doi: 10.1016/j.bbrc.2013.02.052. Epub 2013 Feb 26. PubMed PMID: 23485465. 2: Thota VN, Brahmaiah M, Kulkarni SS. Synthesis of a C-glycoside analogue of β-galactosyl ceramide, a potential HIV-1 entry inhibitor. J Org Chem. 2013 Dec 6;78(23):12082-9. doi: 10.1021/jo402115w. Epub 2013 Nov 15. PubMed PMID: 24199837. 3: Saied EM, Banhart S, Bürkle SE, Heuer D, Arenz C. A series of ceramide analogs modified at the 1-position with potent activity against the intracellular growth of Chlamydia trachomatis. Future Med Chem. 2015;7(15):1971-80. doi: 10.4155/fmc.15.126. Epub 2015 Oct 23. PubMed PMID: 26496536. 4: Liu J, Beckman BS, Foroozesh M. A review of ceramide analogs as potential anticancer agents. Future Med Chem. 2013 Aug;5(12):1405-21. doi: 10.4155/fmc.13.107. Review. PubMed PMID: 23919551; PubMed Central PMCID: PMC4216473. 5: Ballereau S, Levade T, Genisson Y, Andrieu-Abadie N. Alteration of ceramide 1-O-functionalization as a promising approach for cancer therapy. Anticancer Agents Med Chem. 2012 May;12(4):316-28. Review. PubMed PMID: 21554198. 6: Luttgeharm KD, Cahoon EB, Markham JE. A mass spectrometry-based method for the assay of ceramide synthase substrate specificity. Anal Biochem. 2015 Jun 1;478:96-101. doi: 10.1016/j.ab.2015.02.016. Epub 2015 Feb 26. PubMed PMID: 25725359. 7: Shirey CM, Ward KE, Stahelin RV. Investigation of the biophysical properties of a fluorescently modified ceramide-1-phosphate. Chem Phys Lipids. 2016 Oct;200:32-41. doi: 10.1016/j.chemphyslip.2016.06.004. Epub 2016 Jun 16. PubMed PMID: 27318040; PubMed Central PMCID: PMC5159338. 8: Tidhar R, Sims K, Rosenfeld-Gur E, Shaw W, Futerman AH. A rapid ceramide synthase activity using NBD-sphinganine and solid phase extraction. J Lipid Res. 2015 Jan;56(1):193-9. doi: 10.1194/jlr.D052001. Epub 2014 Nov 3. PubMed PMID: 25368106; PubMed Central PMCID: PMC4274067. 9: Garcia V, Le Faouder P, Dupuy A, Levade T, Ballereau S, Génisson Y. A novel jaspine B-ceramide hybrid modulates sphingolipid metabolism. Chem Biodivers. 2015 Jul;12(7):1115-25. doi: 10.1002/cbdv.201400357. PubMed PMID: 26172331. 10: Tokudome Y, Endo M, Hashimoto F. Application of glucosylceramide-based liposomes increased the ceramide content in a three-dimensional cultured skin epidermis. Skin Pharmacol Physiol. 2014;27(1):18-24. doi: 10.1159/000351350. Epub 2013 Jul 24. PubMed PMID: 23887587. 11: Spinedi A. Brefeldin A limits N-hexanoylsphingosine-induced accumulation of natural ceramide via the salvage pathway by enhancing glucosylation. Lipids. 2014 Feb;49(2):207-10. doi: 10.1007/s11745-013-3858-3. Epub 2013 Nov 6. PubMed PMID: 24194457. 12: Hussain H, Nyongha AT, Dongo E, Ahmed I, Zhang W. Melicilamide A: a new ceramide from Milicia excelsa. Nat Prod Res. 2013;27(14):1246-9. doi: 10.1080/14786419.2012.724416. Epub 2012 Sep 11. PubMed PMID: 22963402. 13: Mielke MM, Maetzler W, Haughey NJ, Bandaru VV, Savica R, Deuschle C, Gasser T, Hauser AK, Gräber-Sultan S, Schleicher E, Berg D, Liepelt-Scarfone I. Plasma ceramide and glucosylceramide metabolism is altered in sporadic Parkinson's disease and associated with cognitive impairment: a pilot study. PLoS One. 2013 Sep 18;8(9):e73094. doi: 10.1371/journal.pone.0073094. eCollection 2013. PubMed PMID: 24058461; PubMed Central PMCID: PMC3776817. 14: Couttas TA, Lim XY, Don AS. A three-step assay for ceramide synthase activity using a fluorescent substrate and HPLC. Lipids. 2015 Jan;50(1):101-9. doi: 10.1007/s11745-014-3969-5. Epub 2014 Nov 18. PubMed PMID: 25403920. 15: Korbelik M, Zhang W, Separovic D. Monitoring ceramide and sphingosine-1-phosphate levels in cancer cells and macrophages from tumours treated by photodynamic therapy. Photochem Photobiol Sci. 2012 May;11(5):779-84. doi: 10.1039/c2pp05384e. Epub 2012 Feb 22. PubMed PMID: 22354109. 16: Stock RP, Brewer J, Wagner K, Ramos-Cerrillo B, Duelund L, Jernshøj KD, Olsen LF, Bagatolli LA. Sphingomyelinase D activity in model membranes: structural effects of in situ generation of ceramide-1-phosphate. PLoS One. 2012;7(4):e36003. doi: 10.1371/journal.pone.0036003. Epub 2012 Apr 25. PubMed PMID: 22558302; PubMed Central PMCID: PMC3338491. 17: Kota V, Hama H. 2'-Hydroxy ceramide in membrane homeostasis and cell signaling. Adv Biol Regul. 2014 Jan;54:223-30. doi: 10.1016/j.jbior.2013.09.012. Epub 2013 Oct 8. Review. PubMed PMID: 24139861; PubMed Central PMCID: PMC3946364. 18: Li F, Zhang N. Ceramide: Therapeutic Potential in Combination Therapy for Cancer Treatment. Curr Drug Metab. 2015;17(1):37-51. Review. PubMed PMID: 26526831. 19: Stiban J, Perera M. Very long chain ceramides interfere with C16-ceramide-induced channel formation: A plausible mechanism for regulating the initiation of intrinsic apoptosis. Biochim Biophys Acta. 2015 Feb;1848(2):561-7. doi: 10.1016/j.bbamem.2014.11.018. Epub 2014 Nov 21. PubMed PMID: 25462172. 20: Bergman BC, Brozinick JT, Strauss A, Bacon S, Kerege A, Bui HH, Sanders P, Siddall P, Kuo MS, Perreault L. Serum sphingolipids: relationships to insulin sensitivity and changes with exercise in humans. Am J Physiol Endocrinol Metab. 2015 Aug 15;309(4):E398-408. doi: 10.1152/ajpendo.00134.2015. Epub 2015 Jun 30. PubMed PMID: 26126684; PubMed Central PMCID: PMC4537923.