D,L-erythro-Dihydrosphingosine

This dihydrosphingosine standard is a mixture of D and L isomers and contains approximately 77% erythro and 23% threo isomers. It is an 18 carbon chain which is the most prevalent dihydrosphingosine chain length in most animals. However, some animals, such as Drosophila melanogaster, have the shorter C16 dihydrosphingosine base1 while C20 sphingoid bases are the most prevalent in some microorganisms and are usually the second most abundant sphingoid base in mammals. Dihydrosphingosine (Sphinganine) is the precursor of dihydroceramide which is then desaturated to form ceramide. It is a critical intermediate in the synthesis of many complex sphingoid bases and ceramide analogs. It has been found that sphinganine can induce cell death in a number of types of malignant cells and is being tested for its pharmacological properties.2 Inhibition of dihydroceramide synthesis by some fungal toxins that have a similar structure causes an increase in sphinganine and sphinganine-1-phosphate and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer.3 Sphinganine has been found to mediate fumonisin (a toxic sphinganine analog) induced hypotension.4 In yeast the amount of C20-dihydrosphingosine increases as a response to heat stress, along with other sphingolipids, indicating that it is involved in heat stress adaptation.