MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 597057 | Name: Erythro-sphingosine, (+)-

Description:

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

Erythro-sphingosine, (+)- is a cell-permeable and reversible inhibitor of protein kinase C (IC50 = 12 µM) and enhances src kinase activity. Useful for inhibiting cell surface expression of selectins that promote adhesion of leukocytes or tumor cells to platelets and endothelial cells. Induces apoptosis in human leukemia HL-60 cells.

Chemical Structure

Erythro-sphingosine, (+)-
Erythro-sphingosine, (+)-
CAS#6036-75-5

Theoretical Analysis

MedKoo Cat#: 597057

Name: Erythro-sphingosine, (+)-

CAS#: 6036-75-5

Chemical Formula: C18H37NO2

Exact Mass: 299.2824

Molecular Weight: 299.49

Elemental Analysis: C, 72.19; H, 12.45; N, 4.68; O, 10.68

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.
Bulk Inquiry
Related CAS #
No Data
Synonym
Erythro-sphingosine, (+)-; L-Erythro-c18-sphingosine; L-Erythro-sphingosine;
IUPAC/Chemical Name
(2R,3S,E)-2-aminooctadec-4-ene-1,3-diol
InChi Key
WWUZIQQURGPMPG-MCXRAWCPSA-N
InChi Code
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m1/s1
SMILES Code
CCCCCCCCCCCCC/C=C/[C@H](O)[C@H](N)CO
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 299.49 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: Kong JN, Zhu Z, Itokazu Y, Wang G, Dinkins MB, Zhong L, Lin HP, Elsherbini A, Leanhart S, Jiang X, Qin H, Zhi W, Spassieva SD, Bieberich E. Novel function of ceramide for regulation of mitochondrial ATP release in astrocytes. J Lipid Res. 2018 Mar;59(3):488-506. doi: 10.1194/jlr.M081877. Epub 2018 Jan 10. PubMed PMID: 29321137; PubMed Central PMCID: PMC5832933. 2: Molinski TF, Broaddus CD, Morinaka BI. Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers. Mar Drugs. 2017 Dec 20;15(12). pii: E352. doi: 10.3390/md15120352. PubMed PMID: 29261105; PubMed Central PMCID: PMC5742824. 3: 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. 4: Paz Ramos A, Gooris G, Bouwstra J, Lafleur M. Evidence of hydrocarbon nanodrops in highly ordered stratum corneum model membranes. J Lipid Res. 2018 Jan;59(1):137-143. doi: 10.1194/jlr.M080432. Epub 2017 Nov 1. PubMed PMID: 29092959; PubMed Central PMCID: PMC5748504. 5: Yamane M, Moriya S, Kokuba H. Visualization of ceramide channels in lysosomes following endogenous palmitoyl-ceramide accumulation as an initial step in the induction of necrosis. Biochem Biophys Rep. 2017 Mar 13;11:174-181. doi: 10.1016/j.bbrep.2017.02.010. eCollection 2017 Sep. PubMed PMID: 28955782; PubMed Central PMCID: PMC5614681. 6: Zhang H, Li J, Li L, Liu P, Wei Y, Qian Z. Ceramide enhances COX-2 expression and VSMC contractile hyperreactivity via ER stress signal activation. Vascul Pharmacol. 2017 Sep;96-98:26-32. doi: 10.1016/j.vph.2017.08.001. Epub 2017 Aug 7. PubMed PMID: 28797762. 7: Minnelli C, Cianfruglia L, Laudadio E, Galeazzi R, Pisani M, Crucianelli E, Bizzaro D, Armeni T, Mobbili G. Selective induction of apoptosis in MCF7 cancer-cell by targeted liposomes functionalised with mannose-6-phosphate. J Drug Target. 2018 Mar;26(3):242-251. doi: 10.1080/1061186X.2017.1365873. Epub 2017 Aug 25. PubMed PMID: 28795851. 8: Zhang ZH, Ma FF, Zhang H, Xu XH. MARCKS is Necessary for Oligodendrocyte Precursor Cell Maturation. Neurochem Res. 2017 Oct;42(10):2933-2939. doi: 10.1007/s11064-017-2324-7. Epub 2017 Jun 16. PubMed PMID: 28623606. 9: Rogers MA, Spagnuolo PA, Wang TM, Angka L. A potential bioactive hard-stock fat replacer comprised of a molecular gel. Food Sci Nutr. 2016 Oct 23;5(3):579-587. doi: 10.1002/fsn3.433. eCollection 2017 May. PubMed PMID: 28572944; PubMed Central PMCID: PMC5448365. 10: Pitman MR, Davies LT, Pitson SM. An Improved Isoform-Selective Assay for Sphingosine Kinase 1 Activity. Methods Mol Biol. 2018;1697:9-20. doi: 10.1007/7651_2017_41. PubMed PMID: 28540558. 11: Custódio R, McLean CJ, Scott AE, Lowther J, Kennedy A, Clarke DJ, Campopiano DJ, Sarkar-Tyson M, Brown AR. Characterization of secreted sphingosine-1-phosphate lyases required for virulence and intracellular survival of Burkholderia pseudomallei. Mol Microbiol. 2016 Dec;102(6):1004-1019. doi: 10.1111/mmi.13531. Epub 2016 Sep 26. PubMed PMID: 27632710. 12: Rubil S, Thiel G. Activation of gene transcription via CIM0216, a synthetic ligand of transient receptor potential melastatin-3 (TRPM3) channels. Channels (Austin). 2017 Jan 2;11(1):79-83. doi: 10.1080/19336950.2016.1207026. Epub 2016 Jun 29. PubMed PMID: 27356187; PubMed Central PMCID: PMC5279878. 13: Held K, Voets T, Vriens J. TRPM3 in temperature sensing and beyond. Temperature (Austin). 2015 Feb 25;2(2):201-13. doi: 10.4161/23328940.2014.988524. eCollection 2015 Apr-Jun. Review. PubMed PMID: 27227024; PubMed Central PMCID: PMC4844244. 14: Cheng P, Chen K, Yu W, Gao S, Hu S, Sun X, Huang H. Protein phosphatase 2A (PP2A) activation promotes axonal growth and recovery in the CNS. J Neurol Sci. 2015 Dec 15;359(1-2):48-56. doi: 10.1016/j.jns.2015.10.025. Epub 2015 Oct 21. PubMed PMID: 26671085. 15: Usuki S, Tamura N, Sakai S, Tamura T, Mukai K, Igarashi Y. Chemoenzymatically prepared konjac ceramide inhibits NGF-induced neurite outgrowth by a semaphorin 3A-like action. Biochem Biophys Rep. 2015 Nov 19;5:160-167. doi: 10.1016/j.bbrep.2015.11.016. eCollection 2016 Mar. PubMed PMID: 28955819; PubMed Central PMCID: PMC5600454. 16: Ramos AP, Lafleur M. Chain Length of Free Fatty Acids Influences the Phase Behavior of Stratum Corneum Model Membranes. Langmuir. 2015 Oct 27;31(42):11621-9. doi: 10.1021/acs.langmuir.5b03271. Epub 2015 Oct 15. PubMed PMID: 26442576. 17: Perera MN, Ganesan V, Siskind LJ, Szulc ZM, Bielawska A, Bittman R, Colombini M. Ceramide channel: Structural basis for selective membrane targeting. Chem Phys Lipids. 2016 Jan;194:110-116. doi: 10.1016/j.chemphyslip.2015.09.007. Epub 2015 Sep 25. PubMed PMID: 26408265; PubMed Central PMCID: PMC4718829. 18: Yamane M. Palmitoyl-ceramide accumulation with necrotic cell death in A549 cells, followed by a steep increase in sphinganine content. Biochim Open. 2015 Jun 21;1:11-27. doi: 10.1016/j.biopen.2015.06.001. eCollection 2015. PubMed PMID: 29632826; PubMed Central PMCID: PMC5889477. 19: Xu JD, Xing WM, Yuan TJ, Chen J, Lu H. Metabolic changes in the urine of andrographolide sodium bisulfite-treated rats. Hum Exp Toxicol. 2016 Feb;35(2):162-9. doi: 10.1177/0960327115579429. Epub 2015 Apr 7. PubMed PMID: 25852136. 20: Turgeon CT, Orsini JJ, Sanders KA, Magera MJ, Langan TJ, Escolar ML, Duffner P, Oglesbee D, Gavrilov D, Tortorelli S, Rinaldo P, Raymond K, Matern D. Measurement of psychosine in dried blood spots--a possible improvement to newborn screening programs for Krabbe disease. J Inherit Metab Dis. 2015 Sep;38(5):923-9. doi: 10.1007/s10545-015-9822-z. Epub 2015 Mar 12. PubMed PMID: 25762404.