DL-erythro-Dihydrosphingosine manufacturers
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| | DL-erythro-Dihydrosphingosine Basic information |
| | DL-erythro-Dihydrosphingosine Chemical Properties |
| Melting point | 70-72°C | | Boiling point | 446.2±25.0 °C(Predicted) | | density | 0.927±0.06 g/cm3(Predicted) | | storage temp. | −20°C | | solubility | chloroform/methanol (9:1): 20 mg/mL, clear, colorless to faintly yellow | | form | Solid | | pka | 12.57±0.45(Predicted) | | color | white | | Water Solubility | Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol. | | InChI | InChI=1/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/s3 | | InChIKey | OTKJDMGTUTTYMP-LHIQYTEENA-N | | SMILES | C(O)[C@@H](N)[C@@H](O)CCCCCCCCCCCCCCC |&1:2,4,r| | | CAS DataBase Reference | 3102-56-5(CAS DataBase Reference) |
| | DL-erythro-Dihydrosphingosine Usage And Synthesis |
| Description | DL-erythro Sphinganine (d18:0) is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate . Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers. This product is a mixture of sphinganine (d18:0) , L-erythro sphinganine (d18:0) , D-threo sphinganine (d18:0) , and L-threo sphinganine (d18:0). [Matreya, LLC. Catalog No. 1324] | | Chemical Properties | White Powder | | Uses | Biosynthetic precursor of sphingosine. Inhibits protein kinase C | | Uses | DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor. | | Definition | ChEBI: 2-aminooctadecane-1,3-diol is an aminodiol that is octadecane bearing two hydroxy substituents at positions 1 and 3 as well as an amino substituent at position 2. It is a sphingoid and an aminodiol. | | Biological Functions | Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis. Three stereoisomers,d-erythro-Sph,l-threo-Sph, and dl-erythro-dihydrosphingosine, were tested in the induction of apoptosis and inhibition of MAPK activity in three different kinds of solid tumour cell lines. d-erythro-Sph was strongest in these effects among the three compounds. l-threo-Sphingosine was partly active. On the other hand,dl-erythro-dihydrosphingosine was inactive[1].
| | Biological Activity | Protein kinase C inhibitor. | | storage | -20°C (desiccate) | | Purification Methods | Purify it by recrystallisation from pet ether/EtOAc or CHCl3. The (±)-N-dichloroacetyl derivative has m 142-144o (from MeOH). [Shapiro et al. J Am Chem Soc 80 2170 1958, Shapiro & Sheradsky J Org Chem 28 2157 1963.] The D-isomer crystallises from pet ether/Et2O and has m 78.5-79o, [] 28 +6o (CHCl3/MeOH, 10:1). [Grob & Jenny Helv Chim Acta 35 2106 1953, Jenny & Grob Helv Chim Acta 36 1454 1953, Beilstein 4 I 448, 4 II 757, 4 III 854, 4 IV 1887.] | | References | [1] Chouhei Sakakura . “Selectivity of Sphingosine-Induced Apoptosis.” Biochemical and biophysical research communications 246 3 (1998): Pages 827-830. |
| | DL-erythro-Dihydrosphingosine Preparation Products And Raw materials |
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