D-Sphingosine


Catalog No. size PriceQuantity
M6801-2 2mg solid $98
M6801-10 10mg solid $396

Description

Cas:123-78-4

Product Information

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.

 

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

  • erythro-Sphingosine C-18
  • Sphingosine (d18:1)
  • D-Sphingosine

 

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

 

In Vitro:

A p32-sphingosine-activated protein kinase responds to low concentrations of D-erythro-Sphingosine with an initial activation observed at 2.5 μM and a peak activity at 10-20 μM. This kinase shows a modest specificity for D-erythro-Sphingosine over other sphingosine tereoisomers, and a preference for sphingosines over ihydrosphingosines. D-erythro-Sphingosine inhibits protein kinase C in vitro. D-erythro-Sphingosine has been shown to inhibit protein kinase C, which affects cell regulation and several signal transduction pathways, and exhibits antitumor promoter activities in various mammalian cells.

 

 

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.

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

  1. 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.

 

Products are for research use only. Not for human use.

 

 

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