D-Sphingosine | CAS#123-78-4 | protein kinase C inhibitor

MedKoo Cat#: 330026 | Name: D-Sphingosine

Description:

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

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 Structure

D-Sphingosine

CAS#123-78-4

Theoretical Analysis

MedKoo Cat#: 330026

Name: D-Sphingosine

CAS#: 123-78-4

Chemical Formula: C18H37NO2

Exact Mass: 299.2824

Molecular Weight: 299.50

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

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
200mg	USD 550.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,650.00	2 Weeks
2g	USD 2,650.00	2 Weeks

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Related CAS #

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Synonym

(−)-Sphingosine; D-erythro-Sphingosine C-18; Sphingosine (d18:1); D-Sphingosine; D-erythro-Sphingosine; D-Sphingosine; 4-Sphingenine; Sphing-4-enine;

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

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator.

In vitro activity:

Both synthetic D-erythro-sphingosine and commercial sphingosine inhibited protein kinase C in vitro using vesicle as well as mixed micellar assays. Reference: Biochem Biophys Res Commun. 1990 Oct 30;172(2):683-91. https://pubmed.ncbi.nlm.nih.gov/2241961/

In vivo activity:

Chronic application of d-erythro-sphingosine (DES), the PP2A agonist, to spinal cord-lesioned rats enhanced the activity of this phosphatase and dephosphorylated CRMP2 around the lesion. Reference: J Neurol Sci. 2015 Dec 15;359(1-2):48-56. https://pubmed.ncbi.nlm.nih.gov/26671085/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	0.33
	DMSO	23.7	79.02
	Ethanol	60.0	200.33

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 299.50 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.

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

Formulation protocol:

1. Pushkareva MYu, Bielawska A, Menaldiv D, Liotta D, Hannun YA. Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid bases and inhibition by non-esterified fatty acids. Biochem J. 1993 Sep 15;294 ( Pt 3)(Pt 3):699-703. doi: 10.1042/bj2940699. PMID: 8379926; PMCID: PMC1134519. 2. Khan WA, Dobrowsky R, el Touny S, Hannun YA. 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. doi: 10.1016/0006-291x(90)90728-6. PMID: 2241961. 3. 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. PMID: 26671085. 4. Pinkerton FD, Kisic A, Wilson WK, Schroepfer GJ Jr. D-erythro-sphingosine lowers 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells. Biochem Biophys Res Commun. 1993 Jan 15;190(1):63-9. doi: 10.1006/bbrc.1993.1011. PMID: 8422261.

In vitro protocol:

In vivo protocol:

1. 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. PMID: 26671085. 2. Pinkerton FD, Kisic A, Wilson WK, Schroepfer GJ Jr. D-erythro-sphingosine lowers 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells. Biochem Biophys Res Commun. 1993 Jan 15;190(1):63-9. doi: 10.1006/bbrc.1993.1011. PMID: 8422261.

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