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
• 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

Properties

• 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)

Description

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.

Safety Information

• Hazard Codes: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class: 11 - Combustible Solids
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)