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Tetraacetylphytosphingosine

SIGMA/SMB00703 - ≥98% (HPLC)

Synonym: N-[(1S,2S,3R)-2,3-bis(acetyloxy)-1-[(acetyloxy)methyl]heptadecyl]-acetamide; TAPS

CAS Number: 13018-48-9
Empirical Formula (Hill Notation): C26H47NO7
Molecular Weight: 485.65
Linear Formula: C26H47NO7
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SMB00703-5MG 5 mg
 $131.00
1/EA		 Add To Favorites
45-SMB00703-25MG 25 mg
 $531.00
1/EA		 Add To Favorites
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: SMB00703-25MG.
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: SMB00703-5MG.

 

assay ≥98% (HPLC)
form solid
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
InChI key SGTYQWGEVAMVKB-NXCFDTQHSA-N
lipid type sphingolipids
mp 46 °C
Quality Level 200 
SMILES string N([C@H]([C@H](OC(=O)C)[C@H](OC(=O)C)CCCCCCCCCCCCCC)COC(=O)C)C(=O)C
solubility ethanol: ≤25 mg/mL
storage temp. −20°C
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.
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
mp 46 °C
Storage Temp. −20°C
UNSPSC 12352211

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