Thapsigargin

ChemicalBook > CAS DataBase List > Thapsigargin

Product Name: 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
Formula Weight: 650.75
MOL File: 67526-95-8.mol

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Thapsigargin Property

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)

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T9033
Product name: Thapsigargin
Purity: ≥98% (HPLC), solid film
Packaging: 0.5mg
Price: $124
Updated: 2024/03/01

Sigma-Aldrich

Product number: 586006
Product name: InSolution? Thapsigargin
Packaging: 2mg
Price: $272
Updated: 2024/03/01

Alfa Aesar

Product number: J62866
Product name: Thapsigargin
Purity: 95%
Packaging: 1mg
Price: $147
Updated: 2024/03/01

Alfa Aesar

Product number: J62866
Product name: Thapsigargin
Purity: 95%
Packaging: 5mg
Price: $528.65
Updated: 2024/03/01

Cayman Chemical

Product number: 10522
Product name: Thapsigargin
Purity: ≥97%
Packaging: 1mg
Price: $70
Updated: 2024/03/01

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Thapsigargin Chemical Properties,Usage,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

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View Lastest Price from Thapsigargin manufacturers

Career Henan Chemica Co

Product: THAPSIGARGIN 67526-95-8
Price: US $1.00/g
Min. Order: 1g
Purity: 85.0-99.8%
Supply Ability: 20tons
Release date: 2020-10-28

Dideu Industries Group Limited

Product: THAPSIGARGIN 67526-95-8
Price: US $1.10/g
Min. Order: 1g
Purity: 99.9%
Supply Ability: 100 Tons min
Release date: 2021-08-17

67526-95-8, ThapsigarginRelated Search:

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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