1670-26-4
Chemical Structure
Sphingosylphosphorylcholine
- CAS No.: 1670-26-4
- Formula:C23H49N2O5P
- Molecular Weight:464.62
IUPAC Name: (2S,3R,E)-2-amino-3-hydroxyoctadec-4-en-1-yl (2-(trimethylammonio)ethyl) phosphate
InChIKey: JLVSPVFPBBFMBE-HXSWCURESA-N
SMILES: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@@H](N)COP(OCC[N+](C)(C)C)([O-])=O
Biological Activity: Sphingosylphosphorylcholine is a bioactive lipid and a major component of plasma high-density lipoprotein that binds to OGR1 with a Kd of 33.3 nM. Sphingosylphosphorylcholine triggers delayed phosphorylation of Smad2, upregulates α-SMA expression, and activates TRPM3. Sphingosylphosphorylcholine reduces Apoptosis and upregulates the expression of uPA and its receptor uPA-R. Sphingosylphosphorylcholine exerts anti-apoptotic, anti-cardiac hypertrophy and pro-wound healing effects. Sphingosylphosphorylcholine induces scratching behavior in mice. Sphingosylphosphorylcholine is used in studies related to atopic dermatitis, promyelocytic leukemia, heart failure, myocardial ischemia/reperfusion injury, ovarian cancer, breast cancer, pancreatic cancer, and skin wound healing disorders in genetically impaired healing diabetes[1][2][3][4][5][6][7].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Sphingosylphosphorylcholine | 99.50% | Sphingosylphosphorylcholine is a bioactive lipid and a major component of plasma high-density lipoprotein that binds to OGR1 with a Kd of 33.3 nM. Sphingosylphosphorylcholine triggers delayed phosphorylation of Smad2, upregulates α-SMA expression, and activates TRPM3. Sphingosylphosphorylcholine reduces Apoptosis and upregulates the expression of uPA and its receptor uPA-R. Sphingosylphosphorylcholine exerts anti-apoptotic, anti-cardiac hypertrophy and pro-wound healing effects. Sphingosylphosphorylcholine induces scratching behavior in mice. Sphingosylphosphorylcholine is used in studies related to atopic dermatitis, promyelocytic leukemia, heart failure, myocardial ischemia/reperfusion injury, ovarian cancer, breast cancer, pancreatic cancer, and skin wound healing disorders in genetically impaired healing diabetes. | ||||||||||||||||||||
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Sphingosylphosphorylcholine-d9 | 99.0% | Sphingosylphosphorylcholine-d9 is deuterium labeled Sphingosylphosphorylcholine. | ||||||||||||||||||||
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Sphingosylphosphorylcholine-d7 | 99.90% | Sphingosylphosphorylcholine-d7 is the deuterium labeled Sphingosylphosphorylcholine (HY-132187). | ||||||||||||||||||||
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- [1]. Jeon ES, et al. Sphingosylphosphorylcholine induces differentiation of human mesenchymal stem cells into smooth-muscle-like cells through a TGF-beta-dependent mechanism. J Cell Sci. 2006;119(Pt 23):4994-5005. [Content Brief]
- [2]. Song DE, et al. Sphingosylphosphorylcholine induces itch via activation of TRPM3 and TRPA1 in mice. Biochem Pharmacol. 2025;237:116952. [Content Brief]
- [3]. Kleger A, et al. The bioactive lipid sphingosylphosphorylcholine induces differentiation of mouse embryonic stem cells and human promyelocytic leukaemia cells. Cell Signal. 2007;19(2):367-377. [Content Brief]
- [4]. Ren FF, et al. Sphingosylphosphorylcholine alleviates pressure overload-induced myocardial remodeling in mice via inhibiting CaM-JNK/p38 signaling pathway. Acta Pharmacol Sin. 2024;45(2):312-326. [Content Brief]
- [5]. Herzog C, et al. Intravenous sphingosylphosphorylcholine protects ischemic and postischemic myocardial tissue in a mouse model of myocardial ischemia/reperfusion injury. Mediators Inflamm. 2010;2010:425191. [Content Brief]
- [6]. Xu Y, et al. Sphingosylphosphorylcholine is a ligand for ovarian cancer G-protein-coupled receptor 1. Nat Cell Biol. 2000 May;2(5):261-7. doi: 10.1038/35010529. Retraction in: Nat Cell Biol. 2006 Mar;8(3):299. [Content Brief]
- [7]. Wakita H, et al. Sphingosylphosphorylcholine stimulates proliferation and upregulates cell surface-associated plasminogen activator activity in cultured human keratinocytes. J Invest Dermatol. 1998;110(3):253-258. [Content Brief]
