SMB00703

Tetraacetylphytosphingosine

≥98% (HPLC)

• Synonym(s): N-[(1S,2S,3R)-2,3-bis(acetyloxy)-1-[(acetyloxy)methyl]heptadecyl]-acetamide, TAPS
• Empirical Formula (Hill Notation): C₂₆H₄₇NO₇
• CAS Number: 13018-48-9
• Molecular Weight: 485.65
• UNSPSC Code: 12352211
• NACRES: NA.25

Properties

• Quality Level: 200
• Assay: ≥98% (HPLC)
• form: solid
• mp: 46 °C
• solubility: ethanol: ≤25 mg/mL
• lipid type: sphingolipids
• storage temp.: −20°C
• SMILES string: N([C@H]([C@H](OC(=O)C)[C@H](OC(=O)C)CCCCCCCCCCCCCC)COC(=O)C)C(=O)C
• InChI: 1S/C26H47NO7/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-25(33-22(4)30)26(34-23(5)31)24(27-20(2)28)19-32-21(3)29/h24-26H,6-19H2,1-5H3,(H,27,28)/t24-,25+,26-/m0/s1

Description

Biochem/physiol Actions

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.

TAPS 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.

Other Notes

Due to the low transition temperature of tetraacetylphytosphingosine, the product may be a semi-solid at room temperature.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable