| Identification | More | [Name]
DL-ERYTHRO-DIHYDROSPHINGOSINE | [CAS]
3102-56-5 | [Synonyms]
D-ERTYTHRO-SPHINGANINE, C18 CHAIN
D-ERYTHRO-DIHYDROSPHINGOSINE
D-ERYTHRO-SPHINGANINE
D-ERYTHRO-SPHINGOSINE, DIHYDRO-
DIHYDROSPHINGOSINE
DIHYDROSPHINGOSINE, D-ERYTHRO
DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE
DL-ERYTHRO-2-AMINO-1,3-OCTADECANEDIOL
DL-ERYTHRO-DIHYDROSPHINGOSINE
D,L-ERYTHRO-SPHINGANINE
DL-SPHINGANINE
[R-(R*,S*)]-2-aminooctadecane-1,3-diol
Dihydrosphingosine,Racemic,Synthetic
1,3-Octadecanediol, 2-amino-, (2S,3R)-
(2S,3R)-2-amino-1,3-Octadecanediol
DL-Erythro-DIHYDROSPHINGOSINE Synthetic
DL-erythro-1,3-Dihydroxy-2-aminooctadecane, DL-erythro-2-Amino-1,3-octadecanediol, DL-Sphinganine | [EINECS(EC#)]
212-116-0 | [Molecular Formula]
C18H39NO2 | [MDL Number]
MFCD00079141 | [Molecular Weight]
301.51 | [MOL File]
3102-56-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White Powder | [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. | [Usage]
Biosynthetic precursor of sphingosine. Inhibits protein kinase C | [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) |
| Hazard Information | Back Directory | [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 (Item No. 22500).1 Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers.2,3,4 This product is a mixture of sphinganine (d18:0) (Item No. 10007945), L-erythro sphinganine (d18:0) (Item No. 24374), D-threo sphinganine (d18:0) (Item No. 24375), 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. |
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