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D6908

Sigma-Aldrich

DL-erythro-Dihydrosphingosine

≥99%, synthetic

Synonym(s):
DL-Sphinganine, DL-erythro-1,3-Dihydroxy-2-aminooctadecane, DL-erythro-2-Amino-1,3-octadecanediol
Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
Molecular Weight:
301.51
Beilstein:
1724234
MDL number:
PubChem Substance ID:

biological source

synthetic

assay

≥99%

form

powder

solubility

chloroform/methanol (9:1): 20 mg/mL, clear, colorless to slightly yellow

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCC[C@H](O)[C@H](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/t17-,18+/m1/s1

InChI key

OTKJDMGTUTTYMP-MSOLQXFVSA-N

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Biochem/physiol Actions

D-Isomer is the biosynthetic precursor of sphingosine; inhibits protein kinase C, phospholipase A2, and phospholipase D.

Certificate of Analysis

Certificate of Origin

D D Archibald et al.
Biochimica et biophysica acta, 1166(2-3), 154-162 (1993-02-24)
The natural product D-erythro-sphingosine and synthetic racemic dihydrosphingosines were examined for their abilities to self-assemble into high-axial-ratio microstructures. When precipitated from methanol/water solution, D-erythro-sphingosine formed a viscoelastic gel composed of 50-nm diameter flexible fibers. These are 'cochleate cylinders' composed of...
C Sakakura et al.
Biochemical and biophysical research communications, 246(3), 827-830 (1998-06-10)
Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis (Ohta, et al., Cancer Res., 55, 691-697, 1995). We have recently found that both Sph and its methylated derivative N,N-dimethylsphingosine (DMS) inhibit mitogen-activated protein kinase (MAPK) activity...
Sang-Hun Song et al.
Scientific reports, 9(1), 9834-9834 (2019-07-10)
Surfactants during routine washing have a tremendous effect on lipid loss from hair. This study aims to understand the loss of lipids from hair upon contact with surfactants and develop a way to prevent the lipid loss. The change in...
Emma M Dangerfield et al.
Chembiochem : a European journal of chemical biology, 13(9), 1349-1356 (2012-05-29)
The immunomodulatory glycolipid α-galactosylceramide (α-GalCer) binds to CD1d and exhibits potent activity as a ligand for invariant CD1d-restricted natural killer-like T cells (iNKT cells). Structural analogues of α-GalCer have been synthesised to determine which components are required for CD1d presentation...
Juliana M Figueiredo et al.
Molecular and biochemical parasitology, 182(1-2), 62-74 (2012-01-10)
In this study, we characterized ceramide synthase (CerS) of the protozoan parasite Trypanosoma cruzi at the molecular and functional levels. TcCerS activity was detected initially in a cell-free system using the microsomal fraction of epimastigote forms of T. cruzi, [(3)H]dihydrosphingosine...

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