DL-ERYTHRO-DIHYDROSPHINGOSINE

DL-ERYTHRO-DIHYDROSPHINGOSINE Basic information
Product Name:DL-ERYTHRO-DIHYDROSPHINGOSINE
Synonyms:DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE;DL-ERYTHRO-2-AMINO-1,3-OCTADECANEDIOL;DL-ERYTHRO-DIHYDROSPHINGOSINE;D,L-ERYTHRO-SPHINGANINE;DL-SPHINGANINE;D-ERYTHRO-DIHYDROSPHINGOSINE;D-ERYTHRO-SPHINGANINE;D-ERTYTHRO-SPHINGANINE, C18 CHAIN
CAS:3102-56-5
MF:C18H39NO2
MW:301.51
EINECS:608-571-3
Product Categories:Miscellaneous Natural Products;pharmacetical;Protein Kinase Inhibitors and Activators;Protein Kinase
Mol File:3102-56-5.mol
DL-ERYTHRO-DIHYDROSPHINGOSINE Structure
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
pka12.57±0.45(Predicted)
form Solid
color white
Water Solubility Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol.
CAS DataBase Reference3102-56-5(CAS DataBase Reference)
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
SigmaAldrich English
DL-ERYTHRO-DIHYDROSPHINGOSINE Usage And Synthesis
DescriptionDL-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 PropertiesWhite Powder
UsesBiosynthetic precursor of sphingosine. Inhibits protein kinase C
UsesDL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.
DefinitionChEBI: 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 ActivityProtein kinase C inhibitor.
storage-20°C (desiccate)
Purification MethodsPurify 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.]
DL-ERYTHRO-DIHYDROSPHINGOSINE Preparation Products And Raw materials
KRN7000 C6 NBD SAFINGOL D-ERYTHRO-DIHYDROSPHINGOSINE-1-PHOSPHATE, [4,5-3H] C6 DIHYDROCERAMIDE N-(6-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]CAPROYL)-PHYTOSPHINGOSINE DIHYDROSPHINGOSYLPHOSPHORYLCHOLINE C8 DIHYDROCERAMIDE D-erythro-Dihydro-D-sphingosine-1-phosphate C2 DIHYDROCERAMIDE C14 Dihydroceramide PHYTOSPHINGOSINE DL-ERYTHRO-DIHYDROSPHINGOSINE DIHYDROSPHINGOSINE PHOSPHOCHOLINE, [4,5-3H] C18 Dihydroceramide C4 Dihydroceramide N-[12-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]DODECANOYL]-SPHINGANINE D-ERYTHRO-DIHYDROSPHINGOSINE, [4,5-3H] C16 DIHYDROCERAMIDE

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