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
• Beilstein: 1727294
• EC Number: 204-651-3
• MDL number: MFCD00036751
• UNSPSC Code: 12352211
• PubChem Substance ID: 329824571

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.

Quality

May contain small amounts of structural analogues.

Preparation Note

Prepared from sphingomyelin.

Safety Information

• Hazard Statements: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class Code: 11 - 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