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| Product Name | Thapsigargin |
| Description |
Autophagy inhibitor |
| Purity | >98% (TLC); NMR (Conforms) |
| CAS No. | 67526-95-8 |
| Molecular Formula | C34H50O12 |
| Molecular Weight | 650.8 |
| Field of Use | Not for use in humans. Not for use in diagnostics or therapeutics. For in vitro research use only. |
Properties
| Storage Temperature | -20ºC |
| Shipping Temperature | Shipped Ambient |
| Product Type | Inhibitor |
| Solubility | Soluble in DMSO (65mg/mL); or Ethanol (20mg/mL) |
| Source | Synthetic |
| Appearance | Colorless wax or white solid. |
| SMILES | [C@@H]13C(=C([C@H](OC(=O)C(=CC)/C)[C@H]1OC(=O)CCCCCCC)C)[C@@H]2OC(=O)[C@@](O)([C@@]2(O)[C@@H](OC(=O)CCC)C[C@@]3(OC(=O)C)C) |
| InChI | 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/b1 |
| InChIKey | IXFPJGBNCFXKPI-FSIHEZPISA-N |
| Safety Phrases |
Classification: D1A- Very Toxic Material Causing Immediate and Serious Toxic Effects, Highly Toxic, D2A- Very Toxic Material Causing Other Toxic Effects, Respiratory sensitiser, D2B- Toxic Material Causing Other Toxic Effects, Moderate skin irritant, Moderate eye irritant Safety Phrases: S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. Hazard statements: H315- Causes skin irritation. H319- Causes serious eye irritation. H334- May cause allergy or asthma symptoms or breathing difficulties if inhaled. H335- May cause respiratory irritation. Precautionary statements: P261- Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray. P305 + P351 + P338- IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P342 + P311- If experiencing respiratory symptoms: Call a POISON CENTER or doctor/ physician. |
| Cite This Product | Thapsigargin (StressMarq Biosciences Inc., Victoria BC CANADA, Catalog # SIH-399) |
Biological Description
| Alternative Names | (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 |
| Research Areas | Autophagy, Cancer |
| PubChem ID | 446378 |
| Scientific Background | Thapsigargin is a cell-permeable inhibitor of the sarco-endoplasmatic reticulum Ca2+-ATPase (SERCA). This inhibition causes the release of intracellular Ca2+ stores. Thapsigargin also inhibits autophagy. This is due to the induction of and an ER stress response, which causes downstream effects that include an accumulation of autophagosomes in the cytosol. These intermediate structures never mature into amphisomes and autolysosomes, and the autophagy process cannot be completed. |
| References |
1. Canová N.K., et al. (2007) Cell Biol Toxicol. 23(5): 337-54. 2. Ganley I.G., et al. (2011) Autophagy. 7(11): 1397-9. 3. Cheng Y., et al. (2013) Autophagy. 9(2): 208-19. |
Product Images
Chemical structure of Thapsigargin (SIH-399), a Autophagy inhibitor. CAS #: 67526-95-8. Molecular Formula: C34H50O12. Molecular Weight: 650.8 g/mol.
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