(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
Thapsigargin
CAS: 67526-95-8
Molecular Formula: C34H50O12
(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 - Names and Identifiers
(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 - Physico-chemical Properties
| Molecular Formula | C34H50O12 |
| Molar Mass | 650.75 |
| Density | 1.1521 (rough estimate) |
| Boling Point | 597.77°C (rough estimate) |
| Solubility | DMSO: soluble |
| Appearance | liquid or film |
| Color | Colorless |
| pKa | 10.57±0.70(Predicted) |
| Storage Condition | -20°C |
| 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. |
| Sensitive | Heat and light sensitivity |
| Refractive Index | 1.6390 (estimate) |
| Physical and Chemical Properties | Bioactive Thapsigargin is an effective and non-competitive inhibitor of the sarco/endoplasmic reticulum Ca2 + ATPase (SERCA). IC50 values for carbachol-induced [Ca2 +] I transients in the absence of KCl pre-stimulation are 0.353 nM and 0.448 nM respectively. Thapsigargin can induce apoptosis. Thapsigargin are extracted from plant Thapsia garganica. |
| Use | Use carotene is a widely used inhibitor of endoplasmic reticulum Ca(2 )-ATPases in muscle cells. It acts as a potent, cell-permeable, IP3-independent intracellular calcium-releasing agent that blocks both angiostatin and endostatin-induced transient increases in intracellular Ca2 +. It induces apoptosis by disrupting intracellular free Ca2 + levels. |
(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 - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R42 - May cause sensitization by inhalation |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | RH0325700 |
| HS Code | 29181990 |
(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 - Reference
| Reference Show more | 1. [IF=2.629] Li Yi-Ming et al."Procyanidin B2 Alleviates Palmitic Acid-Induced Injury in HepG2 Cells via Endoplasmic Reticulum Stress Pathway."Evid-Based Compl Alt. 2021;2021:8920757 |
(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 - Introduction
Thapsigargin(Thapsigargin) is a natural product originally isolated from the poisonous carrot tree (Thapsia garganica). It belongs to a class of compounds called "inositol triphosphatase inhibitors", which act primarily by inhibiting the calcium ion pump (SERCA) in the endoplasmic reticulum of cells.
Thapsigargin inhibits the activity of the SERCA calcium pump in cells, resulting in increased intracellular calcium levels. This causes a range of biological responses, including activation of calcium signaling pathways and depletion of intracellular calcium stores. Thapsigargin is mainly used as a research tool for intracellular calcium ions and has received widespread attention due to its specific mechanism of action and high selectivity.
Regarding the preparation method of Thapsigargin, the method of extracting from the poisonous carrot tree is generally used. After extraction, Thapsigargin with high purity can be obtained through a series of chemical treatment and crystallization purification steps.
In terms of safety, Thapsigargin is a strongly toxic compound. It is violently irritating and corrosive, and has potentially damaging effects on the respiratory and digestive systems. Therefore, strict safety measures must be taken when using Thapsigargin, including wearing appropriate personal protective equipment, operating in a well-ventilated laboratory, and complying with chemical waste disposal regulations.
In summary, Thapsigargin is an important tool compound for the Study of intracellular calcium ions. However, due to its high toxicity, it must be used with great care and in accordance with the relevant safety practices.
Thapsigargin inhibits the activity of the SERCA calcium pump in cells, resulting in increased intracellular calcium levels. This causes a range of biological responses, including activation of calcium signaling pathways and depletion of intracellular calcium stores. Thapsigargin is mainly used as a research tool for intracellular calcium ions and has received widespread attention due to its specific mechanism of action and high selectivity.
Regarding the preparation method of Thapsigargin, the method of extracting from the poisonous carrot tree is generally used. After extraction, Thapsigargin with high purity can be obtained through a series of chemical treatment and crystallization purification steps.
In terms of safety, Thapsigargin is a strongly toxic compound. It is violently irritating and corrosive, and has potentially damaging effects on the respiratory and digestive systems. Therefore, strict safety measures must be taken when using Thapsigargin, including wearing appropriate personal protective equipment, operating in a well-ventilated laboratory, and complying with chemical waste disposal regulations.
In summary, Thapsigargin is an important tool compound for the Study of intracellular calcium ions. However, due to its high toxicity, it must be used with great care and in accordance with the relevant safety practices.
Last Update：2024-04-09 21:54:55
![(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](http://res.chembk.com/assets/images/structure/67526-95-8.gif)
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