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SMB00703

Sigma-Aldrich

Tetraacetylphytosphingosine

≥98% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H47NO7
CAS Number:
Molecular Weight:
485.65
UNSPSC Code:
12352211
NACRES:
NA.25

Quality Level

Assay

≥98% (HPLC)

form

solid

mp

46 °C

solubility

ethanol: ≤25 mg/mL

lipid type

sphingolipids

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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