CUSTOMER SERVICE  |  814.355.1030  |  Toll Free: 800.342.3595  |  M-F: 8am-4pm EST/EDT


CATALOG # 1806


  • Catalog #:1806
  • Scientific Name:L-threo-Sphingosine
  • Common Name:L-threo-Sphingosine, C18 chain
  • Empirical Formula:C18H37NO2
  • CAS#:25695-95-8
  • SDS:View Safety Data Sheet
  • Data Sheet:View Data Sheet
  • Formula Weight:300
  • Unit:10 mg
  • Solvent:none
  • Source:synthetic
  • Purity:98+%
  • Analytical Methods:TLC, GC
  • Solubility:ethanol, methanol, chloroform, DMSO
  • Physical Appearance:solid
  • Storage:-20°C
  • Dry Ice:No
  • Hazardous:No


Application Notes:

L-threo-Sphingosine is an inactive or less active isomer of the naturally occurring D-erythro-sphingosine. Natural sphingosine induces dephosphorylation of retinoblastoma gene products and inhibits cell growth while L-threo-sphingosine is less active. However, the L-threo-sphingosine is taken up by cells to the same extent as the natural sphingosine indicating that cellular uptake was not the factor influencing activity.1 L-threo-sphingosine, along with other sphingosine isomers, has been found to be an activator of 3-Phosphoinositide-dependent kinase-1.2 Natural D-erythro-sphingosine is a positive regulator of cell growth in fibroblasts whereas L-threo-sphingosine has no regulatory effect.3 However, non-natural stereoisomers of sphingosine are not always inactive; L-threo-sphingosine has been shown to inhibit protein kinase C a little more potently than D-erythro-sphingosine.4 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. Lysosphingolipids inhibit protein kinase C activity resulting in the pathogenesis of sphingolipidoses such as Krabbe's disease and Gaucher's disease. Sphingosine can be phosphorylated via two kinases to form sphingosine-1-phosphate, which has important signaling functions. While sphingosines and ceramides can induce apoptosis, sphingosine-1-phosphate can promote cell survival or proliferation. Sphingosine has been shown to cause an increase in the cytoplasmic calcium level of cells.

1. Y. Hannun et al. “Stereoselectivity of Induction of the Retinoblastoma Gene Product (pRb) Dephosphorylation by D-erythro-Sphingosine Supports a Role for pRb in Growth Suppression by Sphingosine” Biochemistry, vol. 34 pp. 1885-1892, 1995
2. C. King et al. “Sphingosine Is a Novel Activator of 3-Phosphoinositide-dependent Kinase 1” The Journal of Biological Chemistry, vol. 275(24) pp. 18108-18113, 2000
3. S. Spiegel et al. “Stereospeci~cityo f Sp~ingosine-indu~eIdnt racellular Calcium Mobilization and Cellular Proliferation” Journal of Biological Chemistry, vol. 269 pp. 17924-17930, 1994
4. V. Stevens et al. “Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds” Biochemistry, vol. 28, 3138-3145, 1989
Price $387.00

Others Also Bought

Catalog #:
Catalog #: 1332
CAS#: 383907-87-7
Unit: 25 mg
Catalog #: 1875
CAS#: 89771-78-8
Unit: 1 mg

Customer Reviews

Average Rating
Sign up for news & updates! Sign up!
Please Wait... processing