Tetraacetylphytosphingosine Chemical Properties

Melting point:

46 °C

Boiling point:

594.3±50.0 °C(Predicted)

Density 

1.021±0.06 g/cm3(Predicted)

pka

14.72±0.46(Predicted)

InChIKey

SGTYQWGEVAMVKB-NXCFDTQHSA-N

SMILES

C(N[C@@H](COC(C)=O)[C@H](OC(C)=O)[C@H](OC(C)=O)CCCCCCCCCCCCCC)(=O)C

Tetraacetylphytosphingosine Usage And Synthesis

Description

Tetraacetylphytosphingosine (TAPS) is a sphingolipid metabolite produced by Wickerhamomyces ciferrii (also known as Hansenula ciferrii). It exerts an inhibitory action on angiogenesis through inhibition of the mitogen-activated protein kinase (MAPK) pathway and intracellular calcium increase. Therefore, TAPS was suggested as a potential treatment for angiogenesis related disorders such as arthritis, cancer and psoriasis.

Biological Activity

Tetraacetylphytosphingosine was found to induce apoptosis in HaCaT human keratinocyte cells. In addition, it was demonstrated that TAPS synergistically increases UVB-induced apoptosis via caspase activation by regulating the level of pro-apoptotic Bax and anti-apoptotic Bcl-2 in HaCaT cells.