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D-erythro-Sphingosine C-18

Cayman Chemical Item Number 10007907

(−)-Sphingosine (CAS 123-78-4)

D-erythro-Sphingosine C-18 (CAS 123-78-4)

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Description

D-erythro-Sphingosine is formed primarily from the breakdown of ceramide.1 Sphingosine inhibits protein kinase C and phosphatic acid phosphohydrolase, whereas it activates phospholipase D and diacylglycerol (DAG) kinase.1 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.2,3,4

1 Hannun, Y.A., Luberto, C., and Argraves, K.M. Enzymes of sphingolipid metabolism: From modular to integrative signaling. Biochemistry 40(16) 4893-4903 (2001).

2 Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities. J Biochem 131 767-771 (2002).

3 Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology. Annu Rev Biochem 73 321-354 (2004).

4 Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. Biochim Biophys Acta 1582 72-80 (2002).

Synonyms
  • (-)-Sphingosine
Formal Name 2S-​amino-​4E-​octadecene-​1,​3R-​diol
CAS Number 123-78-4
Molecular Formula C18H37NO2
Formula Weight 299.5
Formulation A crystalline solid
Purity >98%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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OC[C@H]​(N)​[C@H]​(O)​/C=C/CCCCCCCCCCCCC

Background Reading

Hannun, Y.A., Luberto, C., and Argraves, K.M. Enzymes of sphingolipid metabolism: From modular to integrative signaling. Biochemistry 40(16) 4893-4903 (2001).

Takuwa, Y., Takuwa, N., and Sugimoto, N. The Edg family G protein-coupled receptors for lysophospholipids: Their signaling properties and biological activities. J Biochem 131 767-771 (2002).

Kluk, M.J., and Hla, T. Signaling of sphingosine-1-phosphate via the S1P/EDG-family of G-protein-coupled receptors. Biochim Biophys Acta 1582 72-80 (2002).

Ishii, I., Fukushima, N., Ye, X., et al. Lysophospholipid receptors: Signaling and biology. Annu Rev Biochem 73 321-354 (2004).

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D-erythro-Sphingosine C-18 is available in the following screening libraries:

Size Price Quantity Subtotal
10 mg $35.00 $0.00
25 mg $79.00 $0.00
50 mg $140.00 $0.00
100 mg $210.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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