DL-erythro-DihydrosphingosineAn inhibitor of PKC and PLA2

DL-erythro-Dihydrosphingosine (CAS 3102-56-5)

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Synonym: DL-erythro-1,3-Dihydroxy-2-aminooctadecane; DL-erythro-2-Amino-1,3-octadecanediol; DL-Sphinganine
Application: An inhibitor of PKC and PLA2
CAS Number: 3102-56-5
Molecular Weight: 301.51
Molecular Formula: C18H39NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
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DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.


References

Structural requirements for long-chain (sphingoid) base inhibition of protein kinase C in vitro and for the cellular effects of these compounds: A.H. Merrill, Jr., et al.; Biochemistry 28, 3138 (1989) Sphingolipid metabolism and signal transduction: inhibition of in vitro phospholipase activity by sphingosine: R.C. Franson, et al.; Biochim. Biophys. Acta 1136, 169 (1992) Glucocorticoid stimulation of amnion cell prostaglandin synthesis: suppression by protein kinase C inhibitors and independence of phorbol ester-sensitive protein kinase C: T. Zakar, et al.; Biochim. Biophys. Acta 1136, 161 (1992) Sphinganine potentiation of dimethyl sulfoxide-induced granulocyte differentiation, increase of alkaline phosphatase activity and decrease of protein kinase C activity in a human leukemia cell line (HL-60): B.Y. Yung, et al.; BBRC 199, 888 (1994)

Physical State :
Solid
Solubility :
Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol.
Storage :
Store at -20° C
Melting Point :
70-72° C
Boiling Point :
~446.21° C at 760 mmHg (Predicted)
Density :
~0.9 g/cm3 (Predicted)
Refractive Index :
n20D 1.48 (Predicted)
IC50 :
PKC: IC50 = 2.8 µM (chinese hamster ovary cells); Jurkat: IC50 = 3.53 µM (human); Plasmodium falciparum: IC50 = 12.59 µM; CETP: IC50 = 12.9 µM (human); UBC13: IC50 = 13.38 µM (human)
pK Values :
pKa: 12.57 (Predicted), pKb: 8.57 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
6603822
MDL Number :
MFCD07371371
EC Number :
212-116-0
Beilstein Registry :
1724230
SMILES :
CCCCCCCCCCCCCCC[C@@H]([C@@H](CO)N)O

Download SDS (MSDS)

Certificate of Analysis

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