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C8480

D-erythro-Ceramine C8

Name: <SC>D</SC>-<I>erythro</I>-Ceramine C8
Brand: SIGMA

98% (TLC), solid

Synonym(s):

N-Octyl-D-sphingosine

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About This Item

Empirical Formula (Hill Notation):

C₂₆H₅₃NO₂

Molecular Weight:

411.70

MDL number:

MFCD01632747

UNSPSC Code:

12352104

PubChem Substance ID:

329775171

NACRES:

NA.77

Quality Level

100

assay

98% (TLC)

form

solid

color

white

solubility

DMSO: 25 mg/mL
ethanol: 25 mg/mL

storage temp.

−20°C

SMILES string

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

InChI

1S/C26H53NO2/c1-3-5-7-9-11-12-13-14-15-16-17-18-20-22-26(29)25(24-28)27-23-21-19-10-8-6-4-2/h20,22,25-29H,3-19,21,23-24H2,1-2H3/b22-20+/t25-,26+/m0/s1

InChI key

CSRGRGSMEUKQSD-XQAXIDAFSA-N

Biochem/physiol Actions

Inert to ceramidases; induces peak DNA fragmentation in 6 hrs; induces apoptosis in U937 cells.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Stereospecific induction of apoptosis in U937 cells by N-octanoyl-sphingosine stereoisomers and N-octyl-sphingosine. The ceramide amide group is not required for apoptosis.

N Karasavvas et al.

European journal of biochemistry, 236(2), 729-737 (1996-03-01)

We investigated the ability of N-octanoyl-sphingosine (C8-Cer) stereoisomers, N-octanoyl-DL-erythro-dihydrosphingosine (DL-e-DHC8-Cer), and a new ceramide derivative, N-octyl-D-erythro-sphingosine (D-e-C8-Ceramine), to induce apoptosis in U937 cells. We found the C8-Cer stereoisomers to be stereospecific with the D- and L-threo stereoisomers being severalfold more

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