Cas no 67526-95-8 (Thapsigargin)

Thapsigargin is a potent, cell-permeable sesquiterpene lactone that acts as a highly selective inhibitor of the sarco/endoplasmic reticulum Ca2?-ATPase (SERCA) pump. By disrupting calcium homeostasis, it induces endoplasmic reticulum stress and apoptosis, making it a valuable tool for studying cellular stress responses, autophagy, and programmed cell death pathways. Thapsigargin is widely utilized in biomedical research to investigate mechanisms of calcium signaling, cancer biology, and neurodegenerative diseases. Its ability to trigger unfolded protein response (UPR) pathways further enhances its utility in probing ER stress-related phenomena. The compound is known for its high specificity and efficacy, ensuring reliable experimental outcomes in both in vitro and in vivo studies.
Thapsigargin structure
Thapsigargin structure
Product Name:Thapsigargin
CAS No:67526-95-8
MF:C34H50O12
MW:650.75
MDL:MFCD00083511
CID:505196
PubChem ID:24278762
Update Time:2025-10-29

Thapsigargin Chemical and Physical Properties

Names and Identifiers

    • Thapsigargin
    • THAPSIGARGIN(RG)
    • Thapsigargin,(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-
    • Pamoic acid disodium salt
    • rcrawastenumberu217
    • sesquiterpene lactone
    • sesquiterpene lactone tetraester
    • Thallium mononitrate
    • THALLIUM NITRATE
    • thallous
    • THALLOUS NITRATE
    • thallous nitrate TlNO3,orthorhombic
    • Thapsigargin,(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-yloctanoate
    • CHEBI:9516
    • CHEMBL96926
    • UNII-Z96BQ26RZD
    • Z96BQ26RZD
    • [(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
    • Azuleno[4,5-b]furan octanoic acid deriv.
    • (-)-Thapsigargin
    • MFCD00083511
    • HY-13433
    • SCHEMBL82423
    • NCGC00162381-06
    • SR-01000076181
    • AKOS024456410
    • s7895
    • NCGC00261947-01
    • 123269-03-4
    • OCTANOIC ACID [3S-[3ALPHA, 3ABETA, 4ALPHA, 6BETA, 6ABETA, 7BETA, 8ALPHA(Z),
    • (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
    • SDCCGSBI-0051229.P002
    • HMS1791L03
    • GTPL5351
    • HMS1989L03
    • C34H50O12
    • (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-Acetoxy-4-(butyryloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-(((Z)-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
    • EU-0101262
    • THAPSIGARGIN [MI]
    • HMS3402L03
    • n-7-yl ester (9CI)
    • (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-7-yl octanoate
    • 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-(-oxobutoxy)azuleno[4,5-b]furan
    • AC-32567
    • 67526-95-8
    • CS-0006886
    • Q3981006
    • CHEBI:93212
    • HB1118
    • C09561
    • BDBM50035612
    • 9BALPHA]]-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)OX
    • NCGC00016060-08
    • BSPBio_001501
    • Thapsigargin, >=98% (HPLC), solid film
    • SR-01000076181-5
    • Octanoic Acid [3s-[3alpha, 3abeta, 4alpha, 6beta,6abeta, 7beta, 8alpha(Z), 9balpha]]-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
    • HMS3263N06
    • MLS006010944
    • IDI1_033971
    • 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-[3alpha,3abeta,4
    • AS-56389
    • (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-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
    • NCGC00162381-05
    • BRD-K69023402-001-02-5
    • Azuleno[4,5-b]furan, octanoic acid deriv.
    • -7-yl ester
    • octanoic acid {3S-[3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]}-6-(acetoxy)-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
    • LP01262
    • HMS1361L03
    • (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
    • 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]fura
    • 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-(3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha))-
    • TG1
    • SMR001456557
    • LMPR0103410001
    • Y]-2-OXO-4-(1-OXOBUTOXY)-AZULENO[4,5-B]FURAN-7-YL ESTER
    • (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]f uran-7-yl ester
    • Tox21_501262
    • 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
    • T 9033
    • Lopac0_001262
    • CCG-205336
    • SR-01000076181-1
    • OCTANOIC ACID [3S-[3ALPHA, 3ABETA, 4ALPHA, 6BETA, 6ABETA, 7BETA, 8ALPHA(Z), 9BALPHA]]-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)OX Y]-2-OXO-4-(1-OXOBUTOXY)-AZULENO[4,5-B]FURAN-7-YL ESTER
    • alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]]-
    • thapsigargine
    • Tg
    • 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-(3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha))-6-(acetoxy)-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,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-8-(((2Z)-2-methylbut-2-enoyl)oxy)-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno(4,5-b)furan-7-yl octanoate
    • Octanoic acid (3S-(3I+-,3abeta,4I+-,6I2,6abeta,7I2,8I+-(Z),9balpha))-6-(acetoxy)-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
    • Octanoic acid (3S-(3a,3abeta,4a,6b,6abeta,7b,8a(Z),9balpha))-6-(acetoxy)-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,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3,3a-dihydroxy-3,6,9-trimethyl-8-((Z)-2-methylbut-2-enoyl)oxy-2-oxo-4,5,6a,7,8,9b-hexahydroazuleno(4,5-b)furan-7-yl) octanoate
    • (3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-(acetyloxy)-4-(butanoyloxy)-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
    • Octanoate {3S-[3a,3abeta,4a,6b,6abeta,7b,8a(Z),9balpha]}-6-(acetoxy)-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
    • AT23806
    • NCGC00016060-04
    • Octanoate {3S-[3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha]}-6-(acetoxy)-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
    • Octanoate {3S-[3I+-,3abeta,4I+-,6I2,6abeta,7I2,8I+-(Z),9balpha]}-6-(acetoxy)-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
    • DA-68135
    • Octanoic acid {3S-[3a,3abeta,4a,6b,6abeta,7b,8a(Z),9balpha]}-6-(acetoxy)-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
    • IXFPJGBNCFXKPI-FSIHEZPISA-N
    • Octanoate (3S-(3I+-,3abeta,4I+-,6I2,6abeta,7I2,8I+-(Z),9balpha))-6-(acetoxy)-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
    • Octanoate (3S-(3a,3abeta,4a,6b,6abeta,7b,8a(Z),9balpha))-6-(acetoxy)-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
    • Octanoate (3S-(3alpha,3abeta,4alpha,6beta,6abeta,7beta,8alpha(Z),9balpha))-6-(acetoxy)-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
    • DTXCID3020621
    • Octanoic acid {3S-[3I+-,3abeta,4I+-,6I2,6abeta,7I2,8I+-(Z),9balpha]}-6-(acetoxy)-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
    • MDL： MFCD00083511
    • 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： IXFPJGBNCFXKPI-FSIHEZPISA-N
    • SMILES： C(C(=O)O[C@H]1[C@]2([H])[C@@](OC(C)=O)(C[C@@H]([C@@]3([C@](C)(O)C(=O)O[C@]3(C2=C(C)[C@@H]1OC(=O)/C(/C)=C\C)[H])O)OC(CCC)=O)C)CCCCCC

Computed Properties

  • Exact Mass: 650.33000
  • Monoisotopic Mass: 650.33022703g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 12
  • Heavy Atom Count: 46
  • Rotatable Bond Count: 17
  • Complexity: 1270
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: 3.6
  • Topological Polar Surface Area: 172

Experimental Properties

  • Color/Form: Liquid
  • Density: 1.23±0.1 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 597.77°C (rough estimate)
  • Refractive Index: 1.6390 (estimate)
  • Solubility: Insuluble (6.1E-3 g/L) (25 oC),
  • PSA: 171.96000
  • LogP: 3.92790
  • Sensitiveness: Light Sensitive
  • Color/Form: 10?mM in DMSO
  • Solubility: Not determined

Thapsigargin Security Information

  • Symbol: GHS07 GHS08
  • Signal Word：Danger
  • Hazard Statement： H315-H319-H334-H335
  • Warning Statement： P261-P305 + P351 + P338-P342 + P311
  • Hazardous Material transportation number：UN 2811 6.1/PG 2
  • WGK Germany：3
  • Hazard Category Code： 36/37/38-42
  • Safety Instruction： S26; S36/37/39
  • RTECS：RH0325700
  • Hazardous Material Identification： Xn T
  • Storage Condition：Powder -20°C 3 years In solvent -80°C 6 months ? -20°C 1 month
  • Risk Phrases：R36/37/38; R42

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(CAS:67526-95-8)Thapsigargin
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Thapsigargin Related Literature

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Additional information on Thapsigargin

Recent Advances in Thapsigargin (CAS 67526-95-8) Research: Mechanisms and Therapeutic Applications

Thapsigargin (CAS 67526-95-8), a sesquiterpene lactone isolated from the plant Thapsia garganica, has garnered significant attention in recent years due to its potent and selective inhibition of the sarco/endoplasmic reticulum Ca2+-ATPase (SERCA) pump. This compound has emerged as a valuable tool in studying calcium signaling pathways and as a potential therapeutic agent in oncology and other diseases. Recent studies have further elucidated its mechanisms of action and explored novel applications, making it a focal point in chemical biology and drug discovery.

A 2023 study published in *Nature Chemical Biology* demonstrated that Thapsigargin induces endoplasmic reticulum (ER) stress by disrupting calcium homeostasis, leading to the unfolded protein response (UPR) and apoptosis in cancer cells. The research highlighted its efficacy against drug-resistant tumors, particularly in combination with proteasome inhibitors. The study also identified specific biomarkers that predict sensitivity to Thapsigargin, paving the way for personalized cancer therapies.

In addition to its anticancer properties, Thapsigargin has shown promise in antiviral research. A 2024 preprint in *bioRxiv* revealed its broad-spectrum activity against enveloped viruses, including SARS-CoV-2 and influenza, by exploiting host ER stress pathways. This finding suggests potential repurposing opportunities for Thapsigargin in pandemic preparedness, though further clinical validation is required.

Recent structural-activity relationship (SAR) studies have focused on modifying Thapsigargin's scaffold to reduce toxicity while maintaining potency. A team at Scripps Research developed a prodrug version (G-202) that targets prostate-specific membrane antigen (PSMA), showing improved safety profiles in Phase II trials for metastatic castration-resistant prostate cancer. This innovation addresses one of the major limitations of Thapsigargin's clinical translation.

The compound's unique mechanism has also inspired new chemical probes. A 2023 *Journal of Medicinal Chemistry* paper reported fluorophore-conjugated Thapsigargin derivatives for real-time visualization of SERCA inhibition in live cells, offering new tools for studying calcium dynamics in neurodegenerative diseases.

Despite these advances, challenges remain in Thapsigargin's clinical development, particularly regarding its narrow therapeutic window. Ongoing research is exploring nanoparticle delivery systems and combination therapies to mitigate toxicity. The compound continues to serve as both a therapeutic lead and a fundamental research tool, with its full potential yet to be realized in chemical biology and medicine.

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Amadis Chemical Company Limited
(CAS:67526-95-8)Thapsigargin
A1204657
Purity:99%/99%/99%/99%
Quantity:10mg/25mg/50mg/100mg
Price ($):165.0/277.0/475.0/817.0
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