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567726

D-erythro-Sphingosine, Free Base, High Purity

Name: D-<i>erythro-</i>Sphingosine, Free Base, High Purity
Brand: MM

Highly purified preparation of bovine brain sphingosine containing >99% of the erythro isomer.

Synonym(s):

D-erythro-Sphingosine, Free Base, High Purity, Cerebroside, trans-D- erythro-2-Amino-4-octadecene-1,3-diol, Ceramide, Cerebroside, trans-D-erythro-2-Amino-4-octadecene-1,3-diol, Ceramide

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About This Item

Empirical Formula (Hill Notation):

C₁₈H₃₇NO₂

CAS Number:

123-78-4

Molecular Weight:

299.49

UNSPSC Code:

12352211

NACRES:

NA.77

MDL number:

MFCD00036751

Assay:

≥98% (TLC)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze

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Properties

Quality Level

100

description

Merck USA index - 14, 8747

assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze

color

white

solubility

chloroform: 1 mg/mL, methanol: 1 mg/mL, DMSO: 10 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO

InChI

1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

InChI key

WWUZIQQURGPMPG-KRWOKUGFSA-N

Description

General description

Highly purified preparation of bovine brain sphingosine containing >99% of the erythro isomer. A potent, cell-permeable, reversible, and selective inhibitor of protein kinase C (PKC; IC₅₀ = 2.8 µM) and insulin receptor tyrosine kinase. PKC inhibition is competitive with respect to diacylglycerol, phorbol dibutyrate, and Ca²⁺. Does not affect the activity of myosin light chain kinase and protein kinase A. Induces apoptosis in human leukemia HL-60 cells. Note: This product is not to be used for animal treatment, in vivo research or in any other contact procedure with livestock.

Biochem/physiol Actions

Cell permeable: no

Primary Target
PKC

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 2.8 µM against PKC

Preparation Note

Following reconstitution, aliquot, purge with N₂ gas, and freeze (-20°C). Stock solutions are stable for up to 6 months under inert atmosphere at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Irritant (B)

hcodes

H413

pcodes

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c