CAS 67526-95-8

(-)-Thapsigargin

Description:

(-)-Thapsigargin is a natural product derived from the plant Thapsia garganica, belonging to the Apiaceae family. It is a potent inhibitor of the sarco/endoplasmic reticulum Ca²⁺-ATPase (SERCA), which plays a crucial role in calcium homeostasis within cells. This compound is characterized by its ability to induce apoptosis in various cancer cell lines by disrupting calcium signaling pathways. (-)-Thapsigargin is a colorless, crystalline solid that is soluble in organic solvents but has limited solubility in water. Its molecular structure features a complex arrangement of rings and functional groups, contributing to its biological activity. Due to its mechanism of action, (-)-Thapsigargin has been studied for potential therapeutic applications in cancer treatment and other diseases associated with calcium dysregulation. However, its use is limited by its toxicity and the need for careful dosing in experimental settings. Overall, (-)-Thapsigargin serves as an important tool in pharmacological research, particularly in the study of calcium signaling and its implications in disease.

Formula: C₃₄H₅₀O₁₂

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/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1

InChI key: InChIKey=IXFPJGBNCFXKPI-FSIHEZPISA-N

SMILES: O(C(CCCCCCC)=O)[C@H]1[C@]2(C([C@]3([C@](O)([C@@H](OC(CCC)=O)C[C@@]2(OC(C)=O)C)[C@](C)(O)C(=O)O3)[H])=C(C)[C@@H]1OC(/C(=C\C)/C)=O)[H]

Synonyms:

• (-)-Thapsigargin
• (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methyl-2-butenoyl]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,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-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
• Azuleno[4,5-b]furan, octanoic acid deriv.
• 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]furan-7-yl ester
• 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, 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, [3S-[3α,3aβ,4α,6β,6aβ,7β,8α(Z),9bα]]-

Thapsigargin, 95%

CAS: 67526-95-8

Thapsigargin- induces down regulation of the EGF receptor is independent of protein kinase C activation. It is also used as an inducer of stored Ca2+ release. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label informa

Formula: C₃₄H₅₀O₁₂

Purity: 95%

Color and Shape: Wax/film, lyophilized

Molecular weight: 650.76

Ref: 02-J62866

Thapsigargin

CAS: 67526-95-8

Thapsigargin

Formula: C₃₄H₅₀O₁₂

Purity: By hplc: 98.95% (Typical Value in Batch COA)

Color and Shape: white powder

Molecular weight: 650.75g/mol

Ref: 54-BIT4520

Thapsigargin

CAS: 67526-95-8

Thapsigargin

Purity: ≥98%

Molecular weight: 650.75g/mol

Ref: 54-BUP16384

Thapsigargin

CAS: 67526-95-8

Formula: C₃₄H₅₀O₁₂

Purity: (HPLC) ≥ 98.0%

Color and Shape: Colourless film

Molecular weight: 650.75

Ref: 7W-GL5516

Thapsigargin

CAS: 67526-95-8

Thapsigargin is a natural product, an inhibitor of sarcoplasmic/endoplasmic reticulum Ca2+ ATPase (SERCA) and an endoplasmic reticulum stress inducer.

Formula: C₃₄H₅₀O₁₂

Purity: 99.07% - 99.3%

Color and Shape: Colourless Film

Molecular weight: 650.75

Ref: TM-TQ0302

Thapsigargin

Controlled Product

CAS: 67526-95-8

Applications 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.
References Treiman, M. et al.: Trends Pharmacol. Sci., 19, 131 (1998); Korge, P. et al.: Eur. J. Biochem., 265, 273 (1999); Tsukamoto, A. Cell Biol. Int., 17, 969 (1993); Kutinova C.N. et al.: Cell Biol. Toxicol., 23, 337 (2007);

Formula: C₃₄H₅₀O₁₂

Color and Shape: Neat

Molecular weight: 650.75

Ref: TR-T339250

Thapsigargin

CAS: 67526-95-8

Potent inhibitor of SERCA ATPase

Formula: C₃₄H₅₀O₁₂

Purity: Min. 95%

Color and Shape: Colourless Solid

Molecular weight: 650.75 g/mol

Ref: 3D-FT45561