Specifications
- Purity
- ≥97% (TLC)
- Appearance
- White powder
- Identity
- 1H-NMR
Properties
- Solvents
- Soluble in ethanol, DMSO, methanol or chloroform (10mg/ml). Insoluble in water.
Category: Lipids, Fatty Acids
D-Sphingosine is a characteristic structural unit of many sphingolipids such as ceramides, gangliosides, globosides, sulfatides, sphingomyelin, and others. It is most abundant in nervous tissue and cell membranes. Sphingosine with an 18-carbon chain and a double bond at carbon 4 is the most abundant sphingosine in animal tissues. D-Sphingosine inhibits protein kinase C and phosphatidic acid phosphohydrolase, whereas it activates phospholipase D, diacylglycerol (DAG) kinase and the cation channel TRPM3. Phosphorylation of sphingosine by sphingosine kinases 1 and 2 (SPHK 1, SPHK 2) produces sphingosine-1-phosphate, a potent bioactive lipid that exhibits a broad spectrum of biological activities including cell proliferation, survival, migration, cytoskeletal organization and morphogenesis.
Synonyms | (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol, D-erythro-Sphingosine C-18, (-)-Sphingosine |
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Purity | ≥97% (TLC) |
Appearance | White powder |
CAS-Number | 123-78-4 |
Molecular Formula | C18H37NO2 |
Molecular Weight | 299.49 |
Identity | 1H-NMR |
Solvents | Soluble in ethanol, DMSO, methanol or chloroform (10mg/ml). Insoluble in water. |
Smiles | OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCC |
InChi Key | WWUZIQQURGPMPG-KRWOKUGFSA-N |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | -20°C |
Handling Advice | Protect from light and moisture. |
Use / Stability | Stable for at least 2 years after receipt when stored at -20°C. |
Transportation | Not dangerous goods |
References | (1) W.A. Khan, et al., BBRC 172, 683 (1990), (2) W.A. Khan, et al., Biochem. J. 278, 387 (1991), (3) Y.A. Hannun, et al., Biochemistry 40, 4893 (2001), (4) Y. Takuwa, et al., J. Biochem. 131, 767 (2002), (5) M.J. Kluk & T. Hla, Biochim. Biophys. Acta 1582, 72 (2002), (6) I. Ishii, et al., Annu. Rev. Biochem. 73, 321 (2004), (7) H. Nakamura, et al., Eur. J. Pharmacol. 484, 9 (2004), (8) C. Grimm, et al., Mol. Pharmacol. 67, 798 (2005), (9) V.T. Pham, et al., Arch. Pharm. Res. 30, 22 (2007), (10) K. Held, et al., Temperature 2, 201 (2015) |
Quantity | 25 mg, Bulk |