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586006

Sigma-Aldrich

Thapsigargin

≥97% (TLC), liquid, endoplasmic reticular Ca2+-ATPase inhibitor, Calbiochem®

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

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About This Item

Empirical Formula (Hill Notation):
C34H50O12
CAS Number:
67526-95-8
Molecular Weight:
650.75
MDL number:
MFCD00083511
UNSPSC Code:
12352200
NACRES:
NA.77

product name

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

Quality Level

100

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

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
GHS08

signalword

Danger

hcodes

H334

Hazard Classifications

Resp. Sens. 1

wgk_germany

WGK 2

flash_point_f

closed cup

flash_point_c

closed cup

Certificates of Analysis (COA)

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