SMB00703

Tetraacetylphytosphingosine

≥98% (HPLC)

• Sinônimo(s): N-[(1S,2S,3R)-2,3-bis(acetyloxy)-1-[(acetyloxy)methyl]heptadecyl]-acetamide, TAPS
• Fórmula empírica (Notação de Hill): C₂₆H₄₇NO₇
• Número CAS: 13018-48-9
• Peso molecular: 485.65
• Código UNSPSC: 12352211
• NACRES: NA.25

Propriedades

• Nível de qualidade: 200
• Ensaio: ≥98% (HPLC)
• Formulário: solid
• pf: 46 °C
• solubilidade: ethanol: ≤25 mg/mL
• tipo de lipídio: sphingolipids
• temperatura de armazenamento: −20°C
• cadeia de caracteres SMILES: 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
• chave InChI: SGTYQWGEVAMVKB-NXCFDTQHSA-N

Descrição

Ações bioquímicas/fisiológicas

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.

Outras notas

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

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable