Thapsigargin

Base Information

• Chemical Name: Thapsigargin
• CAS No.: 67526-95-8
• Molecular Formula: C₃₄H₅₀O₁₂
• Molecular Weight: 650.764
• Hs Code.: 29181990
• European Community (EC) Number: 614-076-3
• UNII: Z96BQ26RZD
• Nikkaji Number: J34.328E
• Wikipedia: Thapsigargin
• Wikidata: Q3981006
• NCI Thesaurus Code: C128634
• Pharos Ligand ID: 434ZF2SKVWLF
• Metabolomics Workbench ID: 28327
• ChEMBL ID: CHEMBL96926
• Mol file: 67526-95-8.mol

Synonyms:Thapsigargin

Chemical Property of Thapsigargin

Chemical Property:

• Appearance/Colour: colourless film
• Vapor Pressure: 3.78E-22mmHg at 25°C
• Refractive Index: 1.539
• Boiling Point: 691.9 °C at 760 mmHg
• PKA: 10.57±0.70(Predicted)
• Flash Point: 206.1 °C
• PSA: 171.96000
• Density: 1.23 g/cm³
• LogP: 3.92790
• Storage Temp.: -20°C
• Solubility.: DMSO: soluble
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 17
• Exact Mass: 650.33022703
• Heavy Atom Count: 46
• Complexity: 1270

Purity/Quality:

98%,99%, ^*data from raw suppliers

Thapsigargin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: 36/37/38-42
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC(=O)OC1C2C(=C(C1OC(=O)C(=CC)C)C)C3C(C(CC2(C)OC(=O)C)OC(=O)CCC)(C(C(=O)O3)(C)O)O
• Isomeric SMILES: CCCCCCCC(=O)O[C@H]1[C@H]2C(=C([C@@H]1OC(=O)/C(=C\C)/C)C)[C@H]3[C@]([C@H](C[C@]2(C)OC(=O)C)OC(=O)CCC)([C@](C(=O)O3)(C)O)O
• 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.
• 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.

Technology Process of Thapsigargin

There total 51 articles about Thapsigargin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

butanoic acid anhydride (106-31-0) + O8-Debutanoylthapsigargin (105662-35-9) → thiapsigargin (123269-03-4,67526-95-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 1.25h;

DOI:10.1021/ol062947x

Reference yield: 65.0%

Angelic acid (565-63-9) + Octanoic acid (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-4-butyryloxy-3,3a,8-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydro-azuleno[4,5-b]furan-7-yl ester (157160-53-7) → thiapsigargin (123269-03-4,67526-95-8)

Guidance literature:

Angelic acid; With benzoyl chloride; triethylamine; In toluene; at 40 ℃; for 2h; Inert atmosphere;

Octanoic acid (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-4-butyryloxy-3,3a,8-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydro-azuleno[4,5-b]furan-7-yl ester; In toluene; at 90 ℃; for 72h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.09.024

Reference yield:

(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride (137601-32-2) + Octanoic acid (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetoxy-4-butyryloxy-3,3a,8-trihydroxy-3,6,9-trimethyl-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydro-azuleno[4,5-b]furan-7-yl ester (157160-53-7) → thiapsigargin (123269-03-4,67526-95-8)

Guidance literature:

With sodium hydrogencarbonate; In toluene; at 90 ℃; for 45h; Inert atmosphere; Darkness;

DOI:10.1021/jacs.7b01734

upstream raw materials:

butanoic acid anhydride

O₈-Debutanoylthapsigargin

C₂₄H₄₀O₉Si

C₂₉H₄₆O₁₀Si

Refernces

• 1、 -. "SYNTHESIS OF THAPSIGARGIN, NORTRILOBOLIDE, AND ANALOGS THEREOF". . . Retrieved 2018/10/25.
• 2、 Crestey, Fran?ois,Toma, Maddalena,Christensen, S?ren Br?gger. "Concise synthesis of thapsigargin from nortrilobolide". supporting information. p. 5896 - 5898. Retrieved 2015/11/02.