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92609

Sigma-Aldrich

N,N-Dimethylsphingosine

≥98.0% (TLC)

Synonym(s):

(2S,3R,4E)-2-(Dimethylamino)-4-octadecene-1,3-diol, N,N-Dimethyl-D-erythro-sphingosine, N,N-Dimethylsphingenine

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About This Item

Empirical Formula (Hill Notation):
C20H41NO2
CAS Number:
119567-63-4
Molecular Weight:
327.55
MDL number:
MFCD00153960
UNSPSC Code:
12352211
PubChem Substance ID:
329770151

Assay

≥98.0% (TLC)

form

paste

composition

carbon content, 71.9-74.8%
nitrogen content, 4.1-4.5%

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

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

InChI

1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m1/s1

InChI key

YRXOQXUDKDCXME-QWKHPXNBSA-N

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Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCBJ5824V
BCBJ5824
BCBH6565

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S Kimura et al.
Biochemical pharmacology, 44(8), 1585-1595 (1992-10-20)
Neutrophils display three major functions: (i) oxidative burst, (ii) phagokinetic activity, and (iii) trans-endothelial migration. Sphingosine (SPN) is known to inhibit oxidative burst in human neutrophils via inhibition of protein kinase C (PKC). SPN is metabolically converted into N,N-dimethylsphingosine (DMS)
K Endo et al.
Cancer research, 51(6), 1613-1618 (1991-03-15)
Sphingosine (SPN) has been claimed to be a negative modulator of transmembrane signaling through protein kinase C (PK-C) or some yet unidentified mechanism [for review see Y. A. Hannun and R. M. Bell, Science (Washington DC), 243: 500-507, 1989]. N,N-Dimethylsphingosine
Y Igarashi et al.
The Journal of biological chemistry, 265(10), 5385-5389 (1990-04-05)
Our previous study suggested that N,N-dimethylsphingosine, but not unsubstituted sphingosine, could be a modulator of protein kinase C in epidermoid carcinoma A431 cells, since N,N-dimethyl-D-erythrosphingenine showed a stronger stereospecific effect on protein kinase C activity in comparison with N,N-dimethyl-L-erythrosphingenine, unsubstituted
Lei Xiu et al.
The American journal of pathology, 185(2), 387-398 (2014-11-29)
Sphingosine 1-phosphate (S1P) is involved in multiple pathological processes, including fibrogenesis. S1P participates in mouse liver fibrogenesis via a paracrine manner. Herein, we investigated the involvement of S1P in human liver fibrosis. Human fibrotic samples were obtained from livers of

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