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Merck
CN

SMB00703

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:
13018-48-9
Molecular Weight:
485.65
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

Tetraacetylphytosphingosine, ≥98% (HPLC)

SMILES string

N([C@H]([C@H](OC(=O)C)[C@H](OC(=O)C)CCCCCCCCCCCCCC)COC(=O)C)C(=O)C

InChI key

SGTYQWGEVAMVKB-NXCFDTQHSA-N

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

assay

≥98% (HPLC)

form

solid

mp

46 °C

solubility

ethanol: ≤25 mg/mL

lipid type

sphingolipids

storage temp.

−20°C

Quality Level

200

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000286887
0000286888
0000246408
0000286888
0000286887

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H J Kim et al.
Apoptosis : an international journal on programmed cell death, 9(4), 449-456 (2004-06-12)
Inappropriate apoptosis results in the epidermal hyperplasia as in psoriasis and UVB irradiation has been successfully used to treat this kind of skin disorders. Previously, we reported that the novel phytosphingosine derivative, tetraacetyl phytosphingosine (TAPS) induced apoptosis in HaCaT cells.
Studies on the production of sphingolipid bases by the yeast, Hansenula ciferri.
M L Greene et al.
Biochimica et biophysica acta, 98(3), 582-588 (1965-06-01)
Yoo Bin Kwon et al.
Experimental dermatology, 16(4), 311-317 (2007-03-16)
In a search for the wound healing accelerators, we found that tetraacetyl-phytosphingosine (TAPS), a sphingolipid metabolite produced by phytosphingosine acetylation, has significant inhibitory potential on healing of rabbit ear wound. As angiogenesis is fundamental to proper wound healing, we examined

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