E919166 Chemical Structure

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E919166

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Product Description

Catalogue NumberE919166
Chemical Name(+)-(1R,2R,5R)--Ethyl [(2-Hydroxypinan-3-ylene)amino]acetate-13C2
SynonymsN-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene]-glycine Ethyl Ester-13C2; [1R-(1α,2α,5α)]-N-(2-hydroxy-2,6,6-trimethylbicyclo[3.1.1]hept-3-ylidene)-glycine Ethyl Ester-13C2
Alternate CAS #90473-01-1
Molecular FormulaC₁₂¹³C₂H₂₃NO₃
Molecular Weight255.32
Category Building Blocks; Chiral Molecules; Isotopic Labeled Analogues;
Applications(+)-(1R,2R,5R)--Ethyl [(2-Hydroxypinan-3-ylene)amino]acetate-13C2 is an intermediate in the synthesis of D-erythro-Sphingosine-1-phosphate-13C2,D2 (S681502), which is a labelled putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes; mobilizes intracellular calcium stores; decreases cellular cAMP; activates phospholipase D; does not inhibitprotein kinase C.
ReferencesZhang, H., et al.: J. Cell Biol., 114, 155 (1991) Sadahira, Y., et al.: Proc. Natl. Acad. Sci. USA (1992), Cuvillier, O., et al.: Nature, 381, 800 (1996)