D6783
DL-Dihydrosphingosine
≥98%, synthetic
Synonym(s):
1,3-Dihydroxy-2-aminooctadecane, DL-1,3-Dihydroxy-2-aminooctadecane
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About This Item
Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
Molecular Weight:
301.51
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
EC Number:
236-933-7
MDL number:
InChI key
OTKJDMGTUTTYMP-UHFFFAOYSA-N
InChI
1S/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
SMILES string
CCCCCCCCCCCCCCCC(O)C(N)CO
biological source
synthetic
assay
≥98%
form
solid
storage temp.
−20°C
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General description
Dihydrosphingosine is a crucial constituent of the skin lipid barrier, which guards the body from excessive water loss.
Application
DL-Dihydrosphingosine has been used to initiate heat stress signals in Saccharomyces cerevisiae.
Biochem/physiol Actions
Biosynthetic precursor of sphingosine.
Other Notes
Mixture of erythro and threo isomers. Content given on label.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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A Kawamura et al.
Bioorganic & medicinal chemistry, 4(7), 1035-1043 (1996-07-01)
We have developed a simple picomole (low nanogram) scale HPLC scheme which can separate all eight isomers of sphingosine and dihydrosphingosine thus leading to the identification of their relative and absolute configurations. The amino group of the sample is derivatized
Phytosphingosine, sphingosine and dihydrosphingosine ceramides in model skin lipid membranes: permeability and biophysics
vSkolova B, et al.
Biochimica et Biophysica Acta - Biomembranes, 1859(5), 824-834 (2017)
Sphingolipids Are Potential Heat Stress Signals inSaccharomyces
Dickson RC, et al.
The Journal of Biological Chemistry, 272(48), 30196-30200 (1997)
E M Raeder et al.
Blood, 93(2), 686-693 (1999-01-13)
In the present study, we investigated the mechanism by which sphingosine and its analogues, dihydrosphingosine and phytosphingosine, inhibit polymorphonuclear leukocyte (PMN) phagocytosis of IgG-opsonized erythrocytes (EIgG) and inhibit ERK1 and ERK2 phosphorylation. We used antibodies that recognized the phosphorylated forms
Lucila Gisele Pescio et al.
Journal of lipid research, 58(7), 1428-1438 (2017-05-19)
Ceramides (Cers) and complex sphingolipids with defined acyl chain lengths play important roles in numerous cell processes. Six Cer synthase (CerS) isoenzymes (CerS1-6) are the key enzymes responsible for the production of the diversity of molecular species. In this study
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