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T9033

Sigma-Aldrich

Thapsigargin

≥98% (HPLC), solid film

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Synonym(s):
(-)-Thapsigargin, TG1
Empirical Formula (Hill Notation):
C34H50O12
CAS Number:
67526-95-8
Molecular Weight:
650.75
MDL number:
MFCD00083511
UNSPSC Code:
12352200
PubChem Substance ID:
24278762
NACRES:
NA.77

biological source

plant (Thapsia garganica)

Quality Level

300

Assay

≥98% (HPLC)

form

solid film

solubility

acetonitrile: soluble 9.80-10.20 mg/mL
DMSO: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

[H][C@@]12C([C@H](OC([C@]3(O)C)=O)[C@]3(O)[C@@H](OC(CCC)=O)C[C@]2(C)OC(C)=O)=C(C)[C@H](OC(/C(C)=C(C)/[H])=O)[C@H]1OC(CCCCCCC)=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

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General description

Thapsigargin, a guaianolide-type sesquiterpene lactone, is a widely used inhibitor of the ubiquitous sarcoplasmic/endoplasmic reticulum Ca2+ ATPase (SERCA). It can activate endoplasmic reticulum (ER) stress and the unfolded protein response (UPR). Thapsigargin is a natural phytochemical found in the roots and fruits of Mediterranean plants from Thapsia garganica (Apiaceae) species. Thapsigargin promotes the release of translational arrest and induces proteome-wide changes in metabolic pathways within cells infected with coronavirus (CoV).

Application

Thapsigargin has been used as an endoplasmic reticulum (ER) stress inducer:
  • to study its effect on cyclase-associated protein 2 (CAP2) expression in liver cancer cells
  • in the cell viability experiment using ARPE -19 cells (human retinal pigment epithelial cells)
  • to study its effect on lipocalin 2 (LCN2) glycosylation in primary hepatocytes
  • to study the consequences of calcium depletion in the endoplasmic reticulum (ER) of cells
  • to study its effect on tissue inhibitor of metalloproteinases-1 (TIMP-1) mRNA expression in rat Sertoli cells

Biochem/physiol Actions

Thapsigargin is a potent, cell-permeable, IP3-independent intracellular calcium release. It blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. It also induces apoptosis by disrupting intracellular free Ca2+ levels and is incorporated into chemotherapeutic prodrug formulations.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H334,H335

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L M Grønning et al.
Biology of reproduction, 62(4), 1040-1046 (2000-03-22)
In the testis, FSH has been shown to induce the expression and secretion of tissue inhibitor of metalloproteinases-1 (TIMP-1) from Sertoli cells in vitro. This study was performed to elucidate further the cellular origin of testicular TIMP-1 and its expression
Thapsigargin: key to new host-directed coronavirus antivirals?
Shaban MS, et al.
Trends in Pharmacological Sciences (2022)
Thapsigargin-From Traditional Medicine to Anticancer Drug
Agata Jaskulska, et al.
International Journal of Molecular Sciences (2020)
A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca(2+)-ATPases
Treiman M, et al.
Trends in Pharmacological Sciences (1998)
Daryl A Bosco et al.
Human molecular genetics, 19(21), 4160-4175 (2010-08-12)
Mutations in the RNA-binding protein FUS (fused in sarcoma) are linked to amyotrophic lateral sclerosis (ALS), but the mechanism by which these mutants cause motor neuron degeneration is not known. We report a novel ALS truncation mutant (R495X) that leads
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