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Merck

S7049

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

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About This Item

Empirical Formula (Hill Notation):
C18H37NO2
CAS Number:
123-78-4
Molecular Weight:
299.49
UNSPSC Code:
12352211
NACRES:
NA.77
PubChem Substance ID:
24899729
EC Number:
204-651-3
Beilstein/REAXYS Number:
1727294
MDL number:
MFCD00036751

Product Name

D-Sphingosine, synthetic

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

SMILES string

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

biological source

synthetic

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

Quality Level

100

Gene Information

rat ... Prkca(24680)

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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

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2378
MKCN0027
MKCK2512
MKCF5967
MKCC5198

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Susan M Hancock et al.
Nature chemical biology, 5(7), 508-514 (2009-06-16)
Though glycosphingolipids have great potential as therapeutics for cancer, HIV, neurodegenerative diseases and auto-immune diseases, both extensive study of their biological roles and development as pharmaceuticals are limited by difficulties in their synthesis, especially on large scales. Here we addressed
S S Reddy et al.
The Journal of clinical investigation, 84(5), 1569-1576 (1989-11-01)
Leprechaunism is a rare genetic disorder characterized by severe growth retardation and insulin resistance. Maximal epidermal growth factor (EGF) binding was reduced in fibroblasts from three unrelated patients with leprechaunism (Ark-1, Can-1, and Minn-1) compared with control (0.8-2.2%/mg protein vs.
Meret E Ricklin et al.
Neurology, 81(2), 174-181 (2013-05-24)
To study the immune response against varicella-zoster virus (VZV) in patients with multiple sclerosis before and during fingolimod therapy. The VZV-specific immune response was studied using interferon (IFN)-γ enzyme-linked immunosorbent spot assay, proliferation assays, and upregulation of T-cell activation markers
Jeroen Tibboel et al.
Chest, 145(1), 120-128 (2014-01-08)
Sphingolipids comprise a class of bioactive lipids that are involved in a variety of pathophysiologic processes, including cell death and survival. Ceramide and sphingosine-1-phosphate (S1P) form the center of sphingolipid metabolism and determine proapoptotic and antiapoptotic balance. Findings in animal
Vilija G Jokubaitis et al.
Neurology, 82(14), 1204-1211 (2014-03-13)
To determine early risk of relapse after switch from natalizumab to fingolimod; to compare the switch experience to that in patients switching from interferon-β/glatiramer acetate (IFN-β/GA) and those previously treatment naive; and to determine predictors of time to first relapse
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