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Merck
CN

D6908

DL-erythro-Dihydrosphingosine

≥99%, synthetic

Synonym(s):

DL-erythro-1,3-Dihydroxy-2-aminooctadecane, DL-erythro-2-Amino-1,3-octadecanediol, DL-Sphinganine

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About This Item

Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
Molecular Weight:
301.51
PubChem Substance ID:
UNSPSC Code:
12352211
Beilstein/REAXYS Number:
1724234
MDL number:
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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

Biochem/physiol Actions

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


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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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
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
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