D-Sphingosine
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MedKoo CAT#: 330026

CAS#: 123-78-4

Description: Sphingosine is formed primarily from the breakdown of ceramide. Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase. D-sphingosine, a lipid possessing the same hydrophobic base as ceramide but without a carbohydrate residue, efficiently blocked this glycolipid antigen presentation both in vitro and in spinal cords of EAE mice, and significantly decreased IL-17 and ameliorated the pathological symptoms.


Price and Availability

Size Price Shipping out time Quantity
200mg USD 350 2 Weeks
500mg USD 750 2 Weeks
1g USD 1250 2 Weeks
2g USD 2050 2 Weeks
5g USD 4650 2 Weeks
10g USD 6950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-27. Prices are subject to change without notice.

D-Sphingosine is in stock


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 330026
Name: D-Sphingosine
CAS#: 123-78-4
Chemical Formula: C18H37NO2
Exact Mass: 299.2824
Molecular Weight: 299.499
Elemental Analysis: C, 72.19; H, 12.45; N, 4.68; O, 10.68


Synonym: (−)-Sphingosine; D-erythro-Sphingosine C-18; Sphingosine (d18:1); D-Sphingosine;

IUPAC/Chemical Name: 2S-amino-4E-octadecene-1,3R-diol

InChi Key: WWUZIQQURGPMPG-KRWOKUGFSA-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+/m0/s1

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


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).

HS Tariff Code:
2934.99.9001


References

1: Ban Y, Dong W, Zhang L, Zhou T, Altiti AS, Ali K, Mootoo DR, Blaho VA, Hla T, Ren Y, Ma X. Abrogation of Endogenous Glycolipid Antigen Presentation on Myelin- Laden Macrophages by D-Sphingosine Ameliorates the Pathogenesis of Experimental Autoimmune Encephalomyelitis. Front Immunol. 2019 Mar 19;10:404. doi: 10.3389/fimmu.2019.00404. PMID: 30941120; PMCID: PMC6433838.

2: Resuello DL, Lirio SB, Porto AE, Macabeo APG, Huang HY, Corpuz MJT, Villaflores OB. β-secretase 1 inhibitory activity and AMP-activated protein kinase activation of Callyspongia samarensis extracts. Nat Prod Res. 2020 Feb;34(4):525-529. doi: 10.1080/14786419.2018.1488699. Epub 2018 Nov 14. PMID: 30427208.

3: Cleary JM, Lipsky ZW, Kim M, Marques CNH, German GK. Heterogeneous ceramide distributions alter spatially resolved growth of Staphylococcus aureus on human stratum corneum. J R Soc Interface. 2018 Apr;15(141):20170848. doi: 10.1098/rsif.2017.0848. PMID: 29669890; PMCID: PMC5938579.

4: Qi M, Wu C, Wang Z, Zhou L, Men C, Du Y, Huang S, Chen L, Chen L. Transient Receptor Potential Vanilloid 4 Activation-Induced Increase in Glycine-Activated Current in Mouse Hippocampal Pyramidal Neurons. Cell Physiol Biochem. 2018;45(3):1084-1096. doi: 10.1159/000487350. Epub 2018 Feb 7. PMID: 29439248.

5: Pavlova NV, Li SC, Li YT. Degradation of glycosphingolipids in oyster: ceramide glycanase and ceramidase in the hepatopancreas of oyster, Crassostrea virginica. Glycoconj J. 2018 Feb;35(1):77-86. doi: 10.1007/s10719-017-9802-7. Epub 2017 Oct 16. PMID: 29039121.

6: Moreno-Navarrete JM, Moreno M, Ortega F, Xifra G, Hong S, Asara JM, Serrano JCE, Jové M, Pissios P, Blüher M, Ricart W, Portero-Otin M, Fernández-Real JM. TSHB mRNA is linked to cholesterol metabolism in adipose tissue. FASEB J. 2017 Oct;31(10):4482-4491. doi: 10.1096/fj.201700161R. Epub 2017 Jun 23. PMID: 28646016; PMCID: PMC5602896.

7: Selli C, Tosun M. Effects of cyclopiazonic acid and dexamethasone on serotonin-induced calcium responses in vascular smooth muscle cells. J Physiol Biochem. 2016 Jun;72(2):245-53. doi: 10.1007/s13105-016-0474-8. Epub 2016 Mar 4. PMID: 26944908; PMCID: PMC4873523.

8: Zhu W, Wang X, Zhou Y, Wang H. C2-ceramide induces cell death and protective autophagy in head and neck squamous cell carcinoma cells. Int J Mol Sci. 2014 Feb 21;15(2):3336-55. doi: 10.3390/ijms15023336. PMID: 24566153; PMCID: PMC3958915.

9: Jaschinski T, Svatoš A, Pohnert G. Laser desorption/ionization mediated by bionanostructures from microalgae. Rapid Commun Mass Spectrom. 2013 Jan 15;27(1):109-16. doi: 10.1002/rcm.6444. PMID: 23239323.

10: Tibboel J, Joza S, Reiss I, de Jongste JC, Post M. Amelioration of hyperoxia-induced lung injury using a sphingolipid-based intervention. Eur Respir J. 2013 Sep;42(3):776-84. doi: 10.1183/09031936.00092212. Epub 2012 Nov 8. PMID: 23143542.

11: Fischer CL, Walters KS, Drake DR, Blanchette DR, Dawson DV, Brogden KA, Wertz PW. Sphingoid bases are taken up by Escherichia coli and Staphylococcus aureus and induce ultrastructural damage. Skin Pharmacol Physiol. 2013;26(1):36-44. doi: 10.1159/000343175. Epub 2012 Oct 30. PMID: 23128426; PMCID: PMC3634627.

12: Fischer CL, Drake DR, Dawson DV, Blanchette DR, Brogden KA, Wertz PW. Antibacterial activity of sphingoid bases and fatty acids against Gram-positive and Gram-negative bacteria. Antimicrob Agents Chemother. 2012 Mar;56(3):1157-61. doi: 10.1128/AAC.05151-11. Epub 2011 Dec 12. PMID: 22155833; PMCID: PMC3294957.

13: Liang S, Connell GJ. Identification of specific inhibitors for a trypanosomatid RNA editing reaction. RNA. 2010 Dec;16(12):2435-41. doi: 10.1261/rna.2347310. Epub 2010 Oct 12. PMID: 20940340; PMCID: PMC2995404.

14: Fang P, Dong L, Luo JY. Effects of motilin on intracellular free calcium in cultured smooth muscle cells from the antrum of neonatal rats. Acta Physiol (Oxf). 2010 May;199(1):53-61. doi: 10.1111/j.1748-1716.2010.02079.x. Epub 2010 Jan 16. PMID: 20082607.

15: Smith NL, Hammond S, Gadi D, Wagenknecht-Wiesner A, Baird B, Holowka D. Sphingosine derivatives inhibit cell signaling by electrostatically neutralizing polyphosphoinositides at the plasma membrane. Version 2. Self Nonself. 2010;1(2):133-143. doi: 10.4161/self.1.2.11672. PMID: 21423874; PMCID: PMC3058502.

16: Zhang Y, Ranta F, Tang C, Shumilina E, Mahmud H, Föller M, Ullrich S, Häring HU, Lang F. Sphingomyelinase dependent apoptosis following treatment of pancreatic beta-cells with amyloid peptides Abeta(1-42) or IAPP. Apoptosis. 2009 Jul;14(7):878-89. doi: 10.1007/s10495-009-0364-4. PMID: 19488858.

17: Kang JH, Garg H, Sigano DM, Francella N, Blumenthal R, Marquez VE. Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency. Bioorg Med Chem. 2009 Feb 15;17(4):1498-505. doi: 10.1016/j.bmc.2009.01.005. Epub 2009 Jan 11. PMID: 19171486; PMCID: PMC6980351.

18: Chrobak A, Sieradzka U, Sozański R, Chełmońska-Soyta A, Gabryś M, Jerzak M. Ectopic and eutopic stromal endometriotic cells have a damaged ceramide signaling pathway to apoptosis. Fertil Steril. 2009 Dec;92(6):1834-43. doi: 10.1016/j.fertnstert.2008.09.035. Epub 2008 Nov 18. PMID: 19019359.

19: Hisaki H, Okazaki T, Kubota M, Nakane M, Fujimaki T, Nakayama H, Nakagomi T, Tamura A, Masuda H. L-PDMP improves glucosylceramide synthesis and behavior in rats with focal ischemia. Neurol Res. 2008 Nov;30(9):979-84. doi: 10.1179/016164108X339396. Epub 2008 Aug 7. PMID: 18691449.

20: Cho JY. Effect of L-cycloserine on cellular responses mediated by macrophages and T cells. Biol Pharm Bull. 2007 Nov;30(11):2105-12. doi: 10.1248/bpb.30.2105. PMID: 17978484.