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586006

Sigma-Aldrich

Thapsigargin

InSolution, ≥97%, tumor-promoting sesquiterpene lactone

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Synonym(s):
InSolution Thapsigargin, (3 S,3a R,4 S,6 S,6a R,7 S,8 S,9b S)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-((Z)-2-methylbut-2-enoyloxy)-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate, (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-((Z)-2-methylbut-2-enoyloxy)-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate
Empirical Formula (Hill Notation):
C34H50O12
CAS Number:
Molecular Weight:
650.75
MDL number:
NACRES:
NA.77

Quality Level

assay

≥97% (TLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
avoid repeated freeze/thaw cycles
desiccated (hygroscopic)
protect from light

shipped in

dry ice

storage temp.

−70°C

InChI

1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1

InChI key

IXFPJGBNCFXKPI-FSIHEZPISA-N

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Thapsigargin InSolution, ≥97%, tumor-promoting sesquiterpene lactone

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584223

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Leukotriene B4 Potent proinflammatory agent, primarily because of its actions on polymorphonuclear leukocytes that include chemotaxis, aggregation, degranulation, and stimulation of adherence to vascular endothelium.

434625

Leukotriene B4

form

liquid

form

liquid

form

liquid

form

oil

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

−70°C

storage temp.

−70°C

storage temp.

−70°C

storage temp.

−70°C

storage condition

OK to freeze, desiccated (hygroscopic), avoid repeated freeze/thaw cycles, protect from light

storage condition

OK to freeze, avoid repeated freeze/thaw cycles, protect from light

storage condition

OK to freeze

storage condition

OK to freeze

General description

cell-permeable tumor-promoting sesquiterpene lactone that releases Ca2+ by inhibiting endoplasmic reticular Ca2+-ATPase (IC50 = 4 - 13 nM). Does not increase inositol phosphates and has no significant effect on protein kinase C. Increases Ca2+-dependent Na+ influx in human platelets in a dose-dependent manner. Activates apoptosis in rat thymocytes and induces apoptosis in human hepatoma cells.Specifically inhibits the fusion of autophagosomes with lysosomes, and induces autophagy.

Biochem/physiol Actions

Cell permeable: yes
Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Physical form

A 10 mM (2 mg/307 µL) solution of Thapsigargin (Cat. No. 586005) in DMSO.

Other Notes

Won, J.G. and Orth, D.N. 1995. Endocrinology136, 5399.Tepel, M., et al. 1994. Biochim. Biophys. Acta1220, 248.Begum, N., et al. 1993. J. Biol. Chem.268, 3352.Low, A.M., et al. 1993. Eur. J. Pharmacol.230, 53.Tsukamoto, A. and Karneko, Y. 1993. Cell. Biol. Int.17, 969.Wong, W.L., et al. 1993. Biochem. J.289, 71.Glennon, M.C., et al. 1992. J. Biol. Chem.267, 25568.Xu, Y., et al. 1992. J. Neurochem.59, 2224.Mason, M.J., et al. 1991. J. Biol. Chem.266, 20856.Thastrup, O., et al. 1990. Proc. Natl. Acad. Sci. USA87, 2466.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Resp. Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

188.6 °F - (Dimethylsulfoxide)

flash_point_c

87 °C - (Dimethylsulfoxide)


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