All Photos(3)

D6783

Sigma-Aldrich

DL-Dihydrosphingosine

≥98%, synthetic

Synonym(s):
DL-1,3-Dihydroxy-2-aminooctadecane, 1,3-Dihydroxy-2-aminooctadecane
Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
Molecular Weight:
301.51
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

synthetic

assay

≥98%

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCC(O)C(N)CO

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

InChI key

OTKJDMGTUTTYMP-UHFFFAOYSA-N

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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.

Packaging

10, 25, 100 mg in poly bottle

Biochem/physiol Actions

Biosynthetic precursor of sphingosine.

Other Notes

Mixture of erythro and threo isomers. Content given on label.

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Sphingolipids Are Potential Heat Stress Signals inSaccharomyces
Dickson RC, et al.
The Journal of Biological Chemistry, 272(48), 30196-30200 (1997)
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...
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...
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)
Sujeong Jang et al.
Molecules (Basel, Switzerland), 25(16) (2020-08-13)
Cyclodextrins (CDs) are used as drug delivery agents. In this study, we examined whether CDs have an inflammatory effect on endothelial cells. First, we found that β-CD promoted cell proliferation in bovine aortic endothelial cells and elevated nitric oxide (NO)...

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