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2-OHOA | 791056

2-hydroxyoleic acid (sodium salt)

791056P

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791056P-
1g
$152.00

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2-Hydroxy Oleic Acid is an inducer of cell cycle arrest and apoptosis in several cancer cell lines, including glioma, leukemia, breast and colon cancer lines. 2-Hydroxy Oleic Acid increases sphingomyelin (SM) levels in the membranes of tumor cells, which typically display decreased SM membrane content, and remodeled membranes, compared with normal cells. The compound has no effect on SM levels in non-cancer cells.
Molecular Formula
C18H33NaO3
Percent Composition
C 67.47%;,H,10.38%, Na 7.17%, O 14.98%
Purity
>99%
Stability
1 Year
Storage
-20°C
CAS Number
1229114-68-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Molecular Weight
320.443
Exact Mass
320.233
Synonyms
Minerval
NaCHOleate
2OHOA
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Notes
GIF Graphics File. 
GIF Graphics File. 
MDL Molfile. 
CDX File. 
Llado, V., D.J. Lopez, M. Ibarguren, M. Alonso, J.B. Soriano, P.V. Escriba, and X. Busquets. (2014). Regulation of the cancer cell membrane lipid composition by NaCHOleate: Effects on cell signaling and therapeutical relevance in glioma. Biochim Biophys Acta [PubMed]Khmelinskaia, A., M. Ibarguren, R.F. de Almeida, D.J. Lopez, V.A. Paixao, H. Ahyayauch, F.M. Goni, and P.V. Escriba. (2014). Changes in Membrane Organization upon Spontaneous Insertion of 2-Hydroxylated Unsaturated Fatty Acids in the Lipid Bilayer. Langmuir [PubMed]Piotto, S., S. Concilio, E. Bianchino, P. Iannelli, D.J. Lopez, S. Teres, M. Ibarguren, G. Barcelo-Coblijn, M.L. Martin, F. Guardiola-Serrano, M. Alonso-Sande, S.S. Funari, X. Busquets, and P.V. Escriba. (2014). Differential effect of 2-hydroxyoleic acid enantiomers on protein (sphingomyelin synthase) and lipid (membrane) targets. Biochim Biophys Acta [PubMed]Martin, M.L., G. Liebisch, S. Lehneis, G. Schmitz, M. Alonso-Sande, J. Bestard-Escalas, D.H. Lopez, J.M. Garcia-Verdugo, M. Soriano-Navarro, X. Busquets, P.V. Escriba, and G. Barcelo-Coblijn. (2013). Sustained activation of sphingomyelin synthase by 2-hydroxyoleic acid induces sphingolipidosis in tumor cells. J Lipid Res 54:1457-65. [PubMed]Martin, M.L., G. Barcelo-Coblijn, R.F. de Almeida, M.A. Noguera-Salva, S. Teres, M. Higuera, G. Liebisch, G. Schmitz, X. Busquets, and P.V. Escriba. (2013). The role of membrane fatty acid remodeling in the antitumor mechanism of action of 2-hydroxyoleic acid. Biochim Biophys Acta 1828:1405-13. [PubMed]Marcilla-Etxenike, A., M.L. Martin, M.A. Noguera-Salva, J.M. Garcia-Verdugo, M. Soriano-Navarro, I. Dey, P.V. Escriba, and X. Busquets. (2012). 2-Hydroxyoleic acid induces ER stress and autophagy in various human glioma cell lines. PLoS One 7:e48235 [PubMed]Teres, S., V. Llado, M. Higuera, G. Barcelo-Coblijn, M.L. Martin, M.A. Noguera-Salva, A. Marcilla-Etxenike, J.M. Garcia-Verdugo, M. Soriano-Navarro, C. Saus, U. Gomez-Pinedo, X. Busquets, and P.V. Escriba. (2012). Normalization of sphingomyelin levels by 2-hydroxyoleic acid induces autophagic cell death of SF767 cancer cells. Autophagy 8:1542-4. [PubMed]Teres, S., V. Llado, M. Higuera, G. Barcelo-Coblijn, M.L. Martin, M.A. Noguera-Salva, A. Marcilla-Etxenike, J.M. Garcia-Verdugo, M. Soriano-Navarro, C. Saus, U. Gomez-Pinedo, X. Busquets, and P.V. Escriba. (2012). 2-Hydroxyoleate, a nontoxic membrane binding anticancer drug, induces glioma cell differentiation and autophagy. Proc Natl Acad Sci U S A 109:8489-94 [PubMed]Barcelo-Coblijn, G., M.L. Martin, R.F. de Almeida, M.A. Noguera-Salva, A. Marcilla-Etxenike, F. Guardiola-Serrano, A. Luth, B. Kleuser, J.E. Halver, and P.V. Escriba. (2011). Sphingomyelin and sphingomyelin synthase (SMS) in the malignant transformation of glioma cells and in 2-hydroxyoleic acid therapy. Proc Natl Acad Sci U S A 108:19569-74. [PubMed]Llado, V., A. Gutierrez, J. Martinez, J. Casas, S. Teres, M. Higuera, A. Galmes, C. Saus, J. Besalduch, X. Busquets, and P.V. Escriba. (2010). Minerval induces apoptosis in Jurkat and other cancer cells. J Cell Mol Med 14:659-70. [PubMed]