DL-erythro-Dihydrosphingosine
Synonym(s):Sphinganine
- CAS NO.:3102-56-5
- Empirical Formula: C18H39NO2
- Molecular Weight: 301.51
- MDL number: MFCD00079141
- EINECS: 608-571-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-28 23:16:16
What is DL-erythro-Dihydrosphingosine?
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
The Uses of DL-erythro-Dihydrosphingosine
DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.
The Uses of DL-erythro-Dihydrosphingosine
Biosynthetic precursor of sphingosine. Inhibits protein kinase C
What are the applications of Application
DL-erythro-Dihydrosphingosine is an inhibitor of PKC and PLA2
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 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.]
Properties of DL-erythro-Dihydrosphingosine
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 |
CAS DataBase Reference | 3102-56-5(CAS DataBase Reference) |
Safety information for DL-erythro-Dihydrosphingosine
Computed Descriptors for DL-erythro-Dihydrosphingosine
InChIKey | OTKJDMGTUTTYMP-LHIQYTEENA-N |
SMILES | C(O)[C@@H](N)[C@@H](O)CCCCCCCCCCCCCCC |&1:2,4,r| |
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