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D-erythro-Sphingosine (Erythrosphingosine) is a highly potent activator of p32-kinase with an EC50 of 8 μM. D-erythro-Sphingosine inhibits protein kinase C (PKC). It is formed mainly from the breakdown of ceramide. 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.
Physicochemical Properties
| Molecular Formula | C₁₈H₃₇NO₂ |
| Molecular Weight | 299.49 |
| Exact Mass | 299.282 |
| Elemental Analysis | C, 72.19; H, 12.45; N, 4.68; O, 10.68 |
| CAS # | 123-78-4 |
| Related CAS # | D-erythro-Sphingosine hydrochloride;2673-72-5;D-erythro-Sphingosine-d7;1246304-34-6 |
| PubChem CID | 5280335 |
| Appearance | White to off-white solid powder |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 445.9±45.0 °C at 760 mmHg |
| Melting Point | 81-82ºC |
| Flash Point | 223.5±28.7 °C |
| Vapour Pressure | 0.0±2.4 mmHg at 25°C |
| Index of Refraction | 1.489 |
| LogP | 6.4 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 15 |
| Heavy Atom Count | 21 |
| Complexity | 231 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)CO |
| 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 |
| Chemical Name | 2S-amino-4E-octadecene-1,3R-diol |
| Synonyms | Erythrosphingosine erythro-C18-Sphingosine trans-4-Sphingenine(−)-Sphingosine D-erythro-Sphingosine C-18 Sphingosine (d18 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | The p32-sphingosine-activated protein responds to low doses of D-erythro-Sphingosine, with first activation observed at 2.5 μM and maximal activity observed at 10 -20 μM. The potential of sphingosine relative to other sphingosine stereomers, and the preference for sphingosine over hydroisosphingosine [1]. D-erythro-Sphingosine inhibits protein regulatory C in vitro[2]. D-erythro-Sphingosine has been demonstrated to inhibit linked polypeptide C that impacts cell regulation and numerous signal transductions, and demonstrates anti-tumor effect in a range of cells [3]. |
| References |
[1]. Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid basesand inhibition by non-esterified fatty acids. Biochem J. 1993 Sep 15;294 ( Pt 3):699-703. [2]. Protein kinase C and platelet inhibition by D-erythro-Sphingosine: comparison with N,N-dimethylsphingosine and commercial preparation. Biochem Biophys Res Commun. 1990 Oct 30;172(2):683-91. [3]. A concise synthesis of a promising protein kinase C inhibitor: D-erythro-Sphingosine. Arch Pharm Res. 2007 Jan;30(1):22-7. [4]. Protein phosphatase 2A (PP2A) activation promotes axonal growth and recovery in the CNS. J Neurol Sci. 2015 Dec 15;359(1-2):48-56. |
| Additional Infomation |
Sphingosine is a sphing-4-enine in which the double bond is trans. It has a role as a human metabolite and a mouse metabolite. It is a conjugate base of a sphingosine(1+). It is an enantiomer of a L-erythro-sphingosine. An amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed) Sphingosine has been reported in Rehmannia glutinosa, Glycine max, and other organisms with data available. An amino alcohol with a long unsaturated hydrocarbon chain. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. (Dorland, 28th ed) See also: L-erythro-Sphingosine (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~166.95 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.35 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3390 mL | 16.6950 mL | 33.3901 mL | |
| 5 mM | 0.6678 mL | 3.3390 mL | 6.6780 mL | |
| 10 mM | 0.3339 mL | 1.6695 mL | 3.3390 mL |