L-threo-Sphingosine (d18:1)

Sphingosines are long-chain base precursors of cellular sphingolipids and are used directly in the synthesis of ceramide. Sphingosine can exist in four stereoisomers, however only D-erythro-sphingosine occurs naturally. L-threo-Sphingosine C-18, an analog of D-erythro-sphingosine, inhibits protein kinase C in mixed micelle assays with 50% inhibition at 2.2 mol % making it a slightly more potent inhibitor compared to D-erythro-sphingosine (50% inhibition at 2.8 mol %) or other analogs of shorter alkyl chain length. Addition of L-threo-Sphingosine C-18 to primary cultured cerebellar cells does not decrease serine palmitoyltransferase (SPT) activity, the rate-limiting enzyme in ceramide biosynthesis, whereas under similar conditions D-erythro-sphingosine inhibits SPT activity.Formal Name: 2S-amino-4E-octadecene-1,3S-diol. CAS Number: 25695-95-8. Synonyms: L-threo-Sphingosine C18. Molecular Formula: C18H37NO2. Formula Weight: 299.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: Ethanol: 0.25 mg/ml. SMILES: CCCCCCCCCCCCC/C=C/[C@H](O)[C@@H](N)CO. InChi Code: 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-DNWQSSKHSA-N.