DL-erythro-Dihydrosphingosine

Bezeichnung:DL-erythro-Dihydrosphingosine

CAS-Nr3102-56-5

Englisch Name:DL-erythro-Dihydrosphingosine

CBNumberCB6139144

SummenformelC18H39NO2

Molgewicht301.51

MOL-Datei3102-56-5.mol

DL-erythro-Dihydrosphingosine physikalisch-chemischer Eigenschaften

Schmelzpunkt	70-72°C
Siedepunkt	446.2±25.0 °C(Predicted)
Dichte	0.927±0.06 g/cm3(Predicted)
storage temp.	−20°C
Löslichkeit	chloroform/methanol (9:1): 20 mg/mL, clear, colorless to faintly yellow
Aggregatzustand	Solid
pka	12.57±0.45(Predicted)
Farbe	white
Wasserlöslichkeit	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 Datenbank	3102-56-5(CAS DataBase Reference)

Sicherheit

WGK Germany

DL-erythro-Dihydrosphingosine Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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]
Chemische Eigenschaften
White Powder
Verwenden
Biosynthetic precursor of sphingosine. Inhibits protein kinase C
Verwenden
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.
Biologische Funktion
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].
Biologische Aktivität
Protein kinase C inhibitor.
Lager
-20°C (desiccate)
läuterung methode
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.]
Einzelnachweise
[1] Chouhei Sakakura . “Selectivity of Sphingosine-Induced Apoptosis.” Biochemical and biophysical research communications 246 3 (1998): Pages 827-830.

DL-erythro-Dihydrosphingosine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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