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Thapsigargin

Thapsigargin Structure
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
MOL File:
67526-95-8.mol
MSDS File:
SDS
Modify Date:
2023/6/30 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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
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(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) T9033 Thapsigargin ≥98% (HPLC), solid film 67526-95-8 0.5MG ₹12297.2 2022-06-14 Buy
Sigma-Aldrich(India) T9033 Thapsigargin ≥98% (HPLC), solid film 67526-95-8 1MG ₹19950.48 2022-06-14 Buy
Sigma-Aldrich(India) T9033 Thapsigargin ≥98% (HPLC), solid film 67526-95-8 5MG ₹70459.93 2022-06-14 Buy
Sigma-Aldrich(India) T9033 Thapsigargin ≥98% (HPLC), solid film 67526-95-8 10MG ₹112363.5 2022-06-14 Buy
Sigma-Aldrich(India) SML1845 Thapsigargin Ready Made Solution ≥98% (HPLC), 10?mM in DMSO 67526-95-8 4MG ₹59185 2022-06-14 Buy
Product number Packaging Price Buy
T9033 0.5MG ₹12297.2 Buy
T9033 1MG ₹19950.48 Buy
T9033 5MG ₹70459.93 Buy
T9033 10MG ₹112363.5 Buy
SML1845 4MG ₹59185 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.

Thapsigargin Preparation Products And Raw materials

Raw materials

Preparation Products

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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