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Merck
모든 사진(3)

주요 문서

SMB00703

Sigma-Aldrich

Tetraacetylphytosphingosine

≥98% (HPLC)

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C26H47NO7
CAS Number:
Molecular Weight:
485.65
UNSPSC 코드:
12352211
NACRES:
NA.25

Quality Level

분석

≥98% (HPLC)

양식

solid

mp

46 °C

solubility

ethanol: ≤25 mg/mL

지질 유형

sphingolipids

저장 온도

−20°C

SMILES string

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

InChI key

SGTYQWGEVAMVKB-NXCFDTQHSA-N

생화학적/생리학적 작용

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.

기타 정보

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


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문서 라이브러리 방문

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
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)

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