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MedKoo Cat#: 530782 | Name: Sphingosine phosphorylcholine

Description:

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

Sphingosine phosphorylcholine is a wound healing agent.

Chemical Structure

Sphingosine phosphorylcholine
Sphingosine phosphorylcholine
CAS#10216-23-6

Theoretical Analysis

MedKoo Cat#: 530782

Name: Sphingosine phosphorylcholine

CAS#: 10216-23-6

Chemical Formula: C23H50ClN2O5P

Exact Mass: 500.3146

Molecular Weight: 501.09

Elemental Analysis: C, 55.13; H, 10.06; Cl, 7.07; N, 5.59; O, 15.96; P, 6.18

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.
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Related CAS #
No Data
Synonym
Sphingosine phosphorylcholine
IUPAC/Chemical Name
Ethanaminium, 2-((((2-amino-3-hydroxy-4-octadecenyl)oxy)hydroxyphosphinyl)oxy)-N,N,N-trimethyl-, chloride, (R-(R*,S*-(E)))-
InChi Key
OKTWQKXBJUBAKS-OVRPOROMSA-N
InChi Code
InChI=1S/C23H49N2O5P.ClH/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4;/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3;1H/b18-17+;/t22-,23+;/m0./s1
SMILES Code
O=P(OCC[N+](C)(C)C)(OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC)O.[Cl-]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 501.09 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: Yamawaki H. A Novel Regulatory Mechanism for Differentiation of Mesenchymal Stem Cell: Redox State of DJ-1 Matters. Proteomics. 2018 Jan;18(1). doi: 10.1002/pmic.201700345. PubMed PMID: 29194978. 2: Baek S, Lee KP, Jung SH, Cui L, Ko K, Kim B, Won KJ. DJ-1 Regulates Differentiation of Human Mesenchymal Stem Cells into Smooth Muscle-like Cells in Response to Sphingosylphosphorylcholine. Proteomics. 2017 Nov;17(21). doi: 10.1002/pmic.201700208. PubMed PMID: 28949093. 3: Kuchar L, Sikora J, Gulinello ME, Poupetova H, Lugowska A, Malinova V, Jahnova H, Asfaw B, Ledvinova J. Quantitation of plasmatic lysosphingomyelin and lysosphingomyelin-509 for differential screening of Niemann-Pick A/B and C diseases. Anal Biochem. 2017 May 15;525:73-77. doi: 10.1016/j.ab.2017.02.019. Epub 2017 Mar 1. PubMed PMID: 28259515. 4: Kim HJ, Byun HJ, Park MK, Kim EJ, Kang GJ, Lee CH. Novel involvement of RhebL1 in sphingosylphosphorylcholine-induced keratin phosphorylation and reorganization: Binding to and activation of AKT1. Oncotarget. 2017 Mar 28;8(13):20851-20864. doi: 10.18632/oncotarget.15364. PubMed PMID: 28209923; PubMed Central PMCID: PMC5400551. 5: Zhang Y, Zhang M, Lyu B, Kishi H, Kobayashi S. Omega-3 and omega-6 DPA equally inhibit the sphingosylphosphorylcholine-induced Ca(2+)-sensitization of vascular smooth muscle contraction via inhibiting Rho-kinase activation and translocation. Sci Rep. 2017 Feb 7;7:36368. doi: 10.1038/srep36368. PubMed PMID: 28169288; PubMed Central PMCID: PMC5294466. 6: Kemppainen K, Wentus N, Lassila T, Laiho A, Törnquist K. Sphingosylphosphorylcholine regulates the Hippo signaling pathway in a dual manner. Cell Signal. 2016 Dec;28(12):1894-1903. doi: 10.1016/j.cellsig.2016.09.004. Epub 2016 Sep 12. PubMed PMID: 27634386. 7: Bae YC, Choi CW, Nam KW, Song JS, Lee JW. Effects of sphingosylphosphorylcholine on cryopreserved fat tissue graft survival. Mol Med Rep. 2016 Oct;14(4):3719-24. doi: 10.3892/mmr.2016.5677. Epub 2016 Aug 26. PubMed PMID: 27572900. 8: Wirrig C, McKean JS, Wilson HM, Nixon GF. Sphingosylphosphorylcholine inhibits macrophage adhesion to vascular smooth muscle cells. Biochem Pharmacol. 2016 Sep 1;115:43-50. doi: 10.1016/j.bcp.2016.07.004. Epub 2016 Jul 8. PubMed PMID: 27402344; PubMed Central PMCID: PMC4981491. 9: Vanier MT, Gissen P, Bauer P, Coll MJ, Burlina A, Hendriksz CJ, Latour P, Goizet C, Welford RW, Marquardt T, Kolb SA. Diagnostic tests for Niemann-Pick disease type C (NP-C): A critical review. Mol Genet Metab. 2016 Aug;118(4):244-54. doi: 10.1016/j.ymgme.2016.06.004. Epub 2016 Jun 7. Review. PubMed PMID: 27339554. 10: Aksu F, Aksu B, Unlu N, Karaca T, Ayvaz S, Erman H, Uzun H, Keles N, Bulur S, Unlu E. Antioxidant and renoprotective effects of sphingosylphosphorylcholine on contrast-induced nephropathy in rats. Ren Fail. 2016 Aug;38(7):1089-98. doi: 10.1080/0886022X.2016.1194142. Epub 2016 Jun 16. PubMed PMID: 27309733. 11: Li W, Liu H, Liu P, Yin D, Zhang S, Zhao J. Sphingosylphosphorylcholine promotes the differentiation of resident Sca-1 positive cardiac stem cells to cardiomyocytes through lipid raft/JNK/STAT3 and β-catenin signaling pathways. Biochim Biophys Acta. 2016 Jul;1863(7 Pt A):1579-88. doi: 10.1016/j.bbamcr.2016.04.006. Epub 2016 Apr 9. PubMed PMID: 27066979. 12: Lee EJ, Park MK, Kim HJ, Kim EJ, Kang GJ, Byun HJ, Lee CH. Epithelial membrane protein 2 regulates sphingosylphosphorylcholine-induced keratin 8 phosphorylation and reorganization: Changes of PP2A expression by interaction with alpha4 and caveolin-1 in lung cancer cells. Biochim Biophys Acta. 2016 Jun;1863(6 Pt A):1157-69. doi: 10.1016/j.bbamcr.2016.02.007. Epub 2016 Feb 10. PubMed PMID: 26876307. 13: Park MK, Park S, Kim HJ, Kim EJ, Kim SY, Kang GJ, Byun HJ, Kim SH, Lee H, Lee CH. Novel effects of FTY720 on perinuclear reorganization of keratin network induced by sphingosylphosphorylcholine: Involvement of protein phosphatase 2A and G-protein-coupled receptor-12. Eur J Pharmacol. 2016 Mar 15;775:86-95. doi: 10.1016/j.ejphar.2016.02.024. Epub 2016 Feb 9. PubMed PMID: 26872988. 14: El-Najjar N, Orsó E, Wallner S, Liebisch G, Schmitz G. Increased Levels of Sphingosylphosphorylcholine (SPC) in Plasma of Metabolic Syndrome Patients. PLoS One. 2015 Oct 14;10(10):e0140683. doi: 10.1371/journal.pone.0140683. eCollection 2015. PubMed PMID: 26466367; PubMed Central PMCID: PMC4605593. 15: Yokota K, Ogino T. Phase separation in lipid bilayer membranes induced by intermixing at a boundary of two phases with different components. Chem Phys Lipids. 2015 Oct;191:147-52. doi: 10.1016/j.chemphyslip.2015.09.001. Epub 2015 Sep 9. PubMed PMID: 26363303. 16: Hyder CL, Kemppainen K, Isoniemi KO, Imanishi SY, Goto H, Inagaki M, Fazeli E, Eriksson JE, Törnquist K. Sphingolipids inhibit vimentin-dependent cell migration. J Cell Sci. 2015 Jun 1;128(11):2057-69. doi: 10.1242/jcs.160341. Epub 2015 Apr 23. PubMed PMID: 25908861. 17: Yue HW, Liu J, Liu PP, Li WJ, Chang F, Miao JY, Zhao J. Sphingosylphosphorylcholine protects cardiomyocytes against ischemic apoptosis via lipid raft/PTEN/Akt1/mTOR mediated autophagy. Biochim Biophys Acta. 2015 Sep;1851(9):1186-93. doi: 10.1016/j.bbalip.2015.04.001. Epub 2015 Apr 12. PubMed PMID: 25871970. 18: Aksu B, Ayvaz S, Aksu F, Karaca T, Cemek M, Ayaz A, Demirtaş S. Effects of sphingosylphosphorylcholine against oxidative stress and acute lung ınjury ınduced by pulmonary contusion in rats. J Pediatr Surg. 2015 Apr;50(4):591-7. doi: 10.1016/j.jpedsurg.2014.06.007. Epub 2014 Jul 28. PubMed PMID: 25840069. 19: Shaifta Y, Snetkov VA, Prieto-Lloret J, Knock GA, Smirnov SV, Aaronson PI, Ward JP. Sphingosylphosphorylcholine potentiates vasoreactivity and voltage-gated Ca2+ entry via NOX1 and reactive oxygen species. Cardiovasc Res. 2015 Apr 1;106(1):121-30. doi: 10.1093/cvr/cvv029. Epub 2015 Feb 6. PubMed PMID: 25661082; PubMed Central PMCID: PMC4362402. 20: Shirao S, Yoneda H, Shinoyama M, Sugimoto K, Koizumi H, Ishihara H, Oka F, Sadahiro H, Nomura S, Fujii M, Tamechika M, Kagawa Y, Owada Y, Suzuki M. A novel trigger for cholesterol-dependent smooth muscle contraction mediated by the sphingosylphosphorylcholine-Rho-kinase pathway in the rat basilar artery: a mechanistic role for lipid rafts. J Cereb Blood Flow Metab. 2015 May;35(5):835-42. doi: 10.1038/jcbfm.2014.260. Epub 2015 Jan 21. PubMed PMID: 25605290; PubMed Central PMCID: PMC4420858.

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