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S6879

D-Sphingosine

from bovine brain, ~99% (TLC)

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
EC Number:
204-651-3
UNSPSC Code:
12352211
PubChem Substance ID:
329824571
Beilstein/REAXYS Number:
1727294
MDL number:
MFCD00036751
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biological source

bovine brain

assay

~99% (TLC)

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

human ... PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584)

Application

D-Sphingosine from bovine brain was tested for effects on distribution of clathrin/AP-2 in cultured fibroblasts.8 It was used to prepare vesicles and study the interactions of DNA with bilayers of cationic liposomes.9

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.

Preparation Note

Prepared from sphingomyelin.

Analysis Note

May contain small amounts of structural analogues.

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hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
112H8449
093K5202
092H8434
046H5513
041H8449

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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
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
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