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S7049

Sigma-Aldrich

D-Sphingosine

synthetic

Synonym(s):
(2S,3R,4E)-2-Amino-4-octadecene-1,3-diol, 4-Sphingenine, trans-D-erythro-2-Amino-4-octadecene-1,3-diol
Empirical Formula (Hill Notation):
C18H37NO2
CAS Number:
Molecular Weight:
299.49
Beilstein:
1727294
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic

Quality Level

Assay

≥98% (TLC)

form

powder

mp

74.2-78.1 °C

solubility

chloroform: complete 20 mg/mL, clear, colorless

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCC

InChI

1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1

InChI key

WWUZIQQURGPMPG-KRWOKUGFSA-N

Gene Information

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biological source

synthetic

biological source

synthetic

biological source

synthetic

biological source

-

assay

≥98% (TLC)

assay

-

assay

≥99% (HPLC)

assay

99%

form

powder

form

powder

form

solid

form

powder

mp

74.2-78.1 °C

mp

147 °C (dec.) (lit.)

mp

-

mp

>300 °C (lit.)

solubility

chloroform: complete 20 mg/mL, clear, colorless

solubility

water: 50 mg/mL, clear, colorless to light yellow

solubility

methanol: 5 mg/mL, clear, colorless to light yellow

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

Application

The effects of D-Sphingosine, synthetic, on germination activity was studied in the fungus Nomuraea rileyi.8

Biochem/physiol Actions

A constituent of cell membranes. Precursor of ceramide. Selective inhibitor of protein kinase C, but does not inhibit protein kinase A or myosin light chain kinase. Inhibitor of calmodulin-dependent enzymes.
Natural isomer of sphingosine

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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