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Thapsigargin

CAS No.
67526-95-8
Chemical Name:
Thapsigargin
Synonyms
hapsigargin;THAPSIGARGIN;Thapsigargin,97%;Thapsigargin (TG);THAPSIGARGIN USP/EP/BP;InSolution? Thapsigargin;Thapsigargin (10 mM in DMSO);Thapsigargin, FroM Thapsia garganica;Azuleno[4,5-b]furan octanoic acid deriv.;Thapsigargin, 99%, from Thapsia garganica
CBNumber:
CB4768595
Molecular Formula:
C34H50O12
Molecular Weight:
650.75
MDL Number:
MFCD00083511
MOL File:
67526-95-8.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

Thapsigargin Properties

Boiling point 597.77°C (rough estimate)
Density 1.1521 (rough estimate)
refractive index 1.6390 (estimate)
RTECS RH0325700
storage temp. -20°C
solubility DMSO: soluble
form liquid or film
pka 10.57±0.70(Predicted)
color Colorless
Sensitive Light Sensitive
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 week.
CAS DataBase Reference 67526-95-8(CAS DataBase Reference)
FDA UNII Z96BQ26RZD

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H315-H319-H334-H335
Precautionary statements  P261-P264-P271-P302+P352-P304+P340+P312-P305+P351+P338
Hazard Codes  Xn,T
Risk Statements  36/37/38-42
Safety Statements  26-36/37/39
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
HS Code  29181990
NFPA 704
0
2 0

Thapsigargin price More Price(37)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T9033 Thapsigargin ≥98% (HPLC), solid film 67526-95-8 0.5mg $124 2024-03-01 Buy
Sigma-Aldrich 586006 InSolution? Thapsigargin 67526-95-8 2mg $272 2024-03-01 Buy
Alfa Aesar J62866 Thapsigargin 95% 67526-95-8 1mg $147 2024-03-01 Buy
Alfa Aesar J62866 Thapsigargin 95% 67526-95-8 5mg $528.65 2024-03-01 Buy
Cayman Chemical 10522 Thapsigargin ≥97% 67526-95-8 1mg $70 2024-03-01 Buy
Product number Packaging Price Buy
T9033 0.5mg $124 Buy
586006 2mg $272 Buy
J62866 1mg $147 Buy
J62866 5mg $528.65 Buy
10522 1mg $70 Buy

Thapsigargin Chemical Properties,Uses,Production

Description

Thapsigargin is a naturally occurring sesquiterpene lactone isolated from the umbelliferous plant Thapsia garganica. It is a non-competitive, cell permeable inhibitor of calcium transport by SERCAs (IC50 values are cell type-dependent and range from ~2-80 nM). This tumor promoter releases Ca2+ from intracellular stores by specifically inhibiting the endoplasmic reticulum Ca2+-ATPase; it does not directly affect plasma membrane Ca2+-ATPases, Ins 1,4,5-P3 production or protein kinase C activity. This effect is a result of emptying the intracellular calcium stores, which leads to a chain of events that causes apoptosis.

Chemical Properties

Thapsigargin (TG) is colourless film. It is extracted from the plant Thapsia garganica L. with methanol and purified by HPLC. TG is a tumor promoting plant sesquiterpene lactone extract with a unique biological activity as Ca2+ -ATPase inhibitors in animal cells. It is a skin irritant, a platelet activating, inflammatory and tumor promoting agent. TG is toxic and a possible carcinogen.

Uses

THAPSIGARGIN is a widely used inhibitor of the ubiquitous sarco-endoplasmic reticulum Ca(2+)-ATPases in mammalian cells. It acts as a potent, cell-permeable, IP3-independent intracellular calcium releaser that blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. It induces apoptosis by disrupting intracellular free Ca2+ levels.

Definition

ChEBI: Thapsigargin is an organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargin inhibits Ca(2+)-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations. It has a role as an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor and a calcium channel blocker. It is a sesquiterpene lactone, an organic heterotricyclic compound and a butyrate ester.

Biochem/physiol Actions

Thapsigargin is an effective inhibitor of calcium ion pumps located on sarcoplasmic reticulum (SR) and endoplasmic reticulum (ER) microsomes of skeletal, cardiac, muscle and brain tissues. The inhibition of calcium ion pumps causes intracellular increase of calcium ion levels. It was found that thapsigargin at 100 nM concentration effectively inhibited the SR Ca2+- adenosine triphosphatase (ATPase) in cardiac and skeletal muscles. Thapsigargin was also reported to be effective in blocking autophagy by interfering with the autophagosome-lysosome fusion.

storage

Store at -20°C

Mode of action

The actual mechanism of action of thapsigargin is thought actually to block calcium channels in an open conformation that results in excess calcium entry from outside the cell. Excess calcium activates DNAses and precipitates the natural death sequence of the cells.Scientists are now thinking of modifying thapsigargin in such a way thatit will kill prostate cells preferentially and will not penetrate healthy cells elsewhere in the body.At the same time, they are determining whether this drug can also induce cell death in breast cancer cells.

References

1) Treiman et al. (1998), A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca(2+)-ATPases; Trends Pharmacol. Sci., 19 131 2) Zhou et al. (2009), Autophagy-mediated insulin receptor down-regulation contributes to endoplasmic reticulum stress-induced insulin resistance; Mol. Pharmacol., 76 596

Thapsigargin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 147)Suppliers
Supplier Tel Email Country ProdList Advantage
Zhengzhou Alfa Chemical Co.,Ltd
+8618530059196 sale04@alfachem.cn China 12468 58
Hubei Ipure Biology Co., Ltd
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HONG KONG IPURE BIOLOGY CO.,LIMITED
86 18062405514 18062405514 ada@ipurechemical.com CHINA 3465 58
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+86-0576225566889 +86-13454675544 admin@jiuzhou-chem.com;jamie@jiuzhou-chem.com;alice@jiuzhou-chem.com China 20000 58

View Lastest Price from Thapsigargin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
THAPSIGARGIN USP/EP/BP pictures 2021-08-18 THAPSIGARGIN USP/EP/BP
67526-95-8
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited
THAPSIGARGIN pictures 2021-01-06 THAPSIGARGIN
67526-95-8
US $1.00 / g 1g 85.0-99.8% 20tons Career Henan Chemica Co
  • THAPSIGARGIN pictures
  • THAPSIGARGIN
    67526-95-8
  • US $1.00 / g
  • 85.0-99.8%
  • Career Henan Chemica Co
THAPSIGARGIN Octanoic acid, (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]f uran-7-yl ester (3S,3aR,4S,6S,6AR,7S,8S,9bS)-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[[(2Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl octanoate Octanoic acid [(3S)-6α-acetoxy-2,3,3a,4,5,6,6aα,7,8,9bβ-decahydro-3β,3aα-dihydroxy-3,6,9-trimethyl-8β-[[(Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4β-(1-oxobutoxy)azuleno[4,5-b]furan]-7α-yl ester Thapsigargin,97% Octanoic Acid (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b- decahydro-3,3a-dihydroxy-3,6,9-triMethyl-8-[[(2Z)-2-Methyl-1-oxo-2-butenyl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester Octanoic Acid [3S-[3α,3aβ,4α,6β,6aβ,7β,8α(Z),9bα]]-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-triMethyl-8-[(2-Methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester Thapsigargin (TG) Thapsigargin, FroM Thapsia garganica Azuleno[4,5-b]furan octanoic acid deriv. Thapsigargin Azuleno[4,5-b]furan octanoic acid deriv InSolution? Thapsigargin Thapsigargin, 99%, from Thapsia garganica Thapsigargin - CAS 67526-95-8 - Calbiochem InSolution Thapsigargin - CAS 67526-95-8 - Calbiochem Thapsigargin (Synonyms: Thapsigargin (TG)) THAPSIGARGIN USP/EP/BP (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3... (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate [(3S,3aR,4S,6S,6aS,7S,8S,9bR)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-(2-methylbut-2-enoyloxy)-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate hapsigargin (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-(((Z)-2-methylbut-2-enoyl)oxy)-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-7-yl octanoate Thapsigargin (10 mM in DMSO) 67526-95-8 C34H50O12 BioChemical Cell Signaling and Neuroscience Cell Biology Intracellular Calcium Regulators Intracellular Calcium Signaling plantgrowth Adenosinetriphosphatase (microsomal calcium)Cell Signaling and Neuroscience Antitumor Agents Intracellular Calcium RegulatorsCancer Research Intracellular Calcium Signaling Therapy Adjuncts A to Enzyme Inhibitors by Enzyme Calcium signaling Signalling Apoptosis Heterocycles Inhibitors Intermediates & Fine Chemicals Pharmaceuticals