586006

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
• Empirical Formula (Hill Notation): C₃₄H₅₀O₁₂
• CAS Number: 67526-95-8
• Molecular Weight: 650.75
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00083511
• Assay: ≥97% (TLC)
• Form: liquid
• Storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

Properties

• Product Name: Thapsigargin, InSolution, ≥97%, tumor-promoting sesquiterpene lactone
• Quality Segment: 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
• SMILES string: O1[C@@H]2[C@]([C@H](C[C@@]([C@H]3[C@@H]([C@H](C(=C32)C)OC(=O)\C(=C/C)\C)OC(=O)CCCCCCC)(OC(=O)C)C)OC(=O)CCC)([C@@](C1=O)(O)C)O
• 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

Description

General description

A 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

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

Disclaimer

Toxicity: Irritant (B)

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Codes: H334
• Precautionary Statements: P261 - P284 - P501
• Hazard Classifications: Resp. Sens. 1
• Storage Class: 10 - Combustible liquids
• WGK: WGK 2
• Flash Point (°F): 188.6 °F - closed cup - (Dimethylsulfoxide)
• Flash Point (°C): 87 °C - closed cup - (Dimethylsulfoxide)