Thapsigargin

Autophagy inhibitor

Catalog No. SIH-399

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CAS No. 67526-95-8
Molecular Formula C34H50O12
SKU: SIH-399 Categories: ,

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SIH-399_Thapsigargin_Chemical_Structure.png
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

<p>Chemical structure of Thapsigargin (SIH-399), a Autophagy inhibitor. CAS #: 67526-95-8. Molecular Formula: C34H50O12. Molecular Weight: 650.8 g/mol.</p>

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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