SMB00703

Tetraacetylphytosphingosine

≥98% (HPLC)

• Synonyme(s) : N-[(1S,2S,3R)-2,3-bis(acetyloxy)-1-[(acetyloxy)methyl]heptadecyl]-acetamide, TAPS
• Formule empirique (notation de Hill) : C₂₆H₄₇NO₇
• Numéro CAS: 13018-48-9
• Poids moléculaire : 485.65
• Code UNSPSC : 12352211
• Nomenclature NACRES : NA.25

Propriétés

• Niveau de qualité: 200
• Essai: ≥98% (HPLC)
• Forme: solid
• Pf: 46 °C
• Solubilité: ethanol: ≤25 mg/mL
• Type de lipide: sphingolipids
• Température de stockage: −20°C
• Chaîne 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
• Clé InChI: SGTYQWGEVAMVKB-NXCFDTQHSA-N

Description

Actions biochimiques/physiologiques

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.

Autres remarques

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

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable