Skip to Content
Merck
All Photos(1)

Key Documents

T9033

Sigma-Aldrich

Thapsigargin

≥98% (HPLC), solid film

Synonym(s):

(-)-Thapsigargin, TG1

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C34H50O12
CAS Number:
Molecular Weight:
650.75
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

plant (Thapsia garganica)

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

Potent, cell-permeable, IP3-independent intracellular calcium releaser.
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.

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Nicole S Hou et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(22), E2271-E2280 (2014-05-21)
The Mediator is a conserved transcriptional coregulator complex required for eukaryotic gene expression. In Caenorhabditis elegans, the Mediator subunit mdt-15 is essential for the expression of genes involved in fatty acid metabolism and ingestion-associated stress responses. mdt-15 loss of function
Jing Deng et al.
Molecular and cellular biology, 24(23), 10161-10168 (2004-11-16)
Numerous stressful conditions activate kinases that phosphorylate the alpha subunit of translation initiation factor 2 (eIF2alpha), thus attenuating mRNA translation and activating a gene expression program known as the integrated stress response. It has been noted that conditions associated with
Maximilien Tailler et al.
Cell death and differentiation, 26(9), 1766-1781 (2018-12-13)
Drugs targeting various pro-survival BCL-2 family members (''BH3 mimetics'') have efficacy in hemopoietic malignancies, but the non-targeted pro-survival family members can promote resistance. Pertinently, the sensitivity of some tumor cell lines to BH3 mimetic ABT737, which targets BCL-2, BCL-XL, and
V Shinde et al.
Cell death & disease, 7, e2085-e2085 (2016-02-06)
The molecular mechanism of autosomal dominant retinitis pigmentosa (ADRP) in rats is closely associated with a persistently activated unfolded protein response (UPR). If unchecked, the UPR might trigger apoptosis, leading to photoreceptor death. One of the UPR-activated cellular signaling culminating

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service