Trilobolide
[CAS# 50657-07-3]

Identification

• Name: Trilobolide
• Synonyms: [(3S,3Ar,4S,6S,6As,8R,9Bs)-6-Acetoxy-3,3A-Dihydroxy-3,6,9-Trimethyl-4-[(2S)-2-Methylbutanoyl]Oxy-2-Oxo-4,5,6A,7,8,9B-Hexahydroazuleno[4,5-B]Furan-8-Yl] (Z)-2-Methylbut-2-Enoate; (Z)-2-Methylbut-2-Enoic Acid [(3S,3Ar,4S,6S,6As,8R,9Bs)-6-Acetoxy-3,3A-Dihydroxy-3,6,9-Trimethyl-4-[(2S)-2-Methyl-1-Oxobutoxy]-2-Oxo-4,5,6A,7,8,9B-Hexahydroazuleno[4,5-B]Furan-8-Yl] Ester; (Z)-2-Methylbut-2-Enoic Acid [(3S,3Ar,4S,6S,6As,8R,9Bs)-6-Acetoxy-3,3A-Dihydroxy-2-Keto-3,6,9-Trimethyl-4-[(2S)-2-Methylbutanoyl]Oxy-4,5,6A,7,8,9B-Hexahydroazuleno[4,5-B]Furan-8-Yl] Ester
• Molecular Formula: C₂₇H₃₈O₁₀
• Molecular Weight: 522.59
• CAS Registry Number: 50657-07-3
• SMILES: [C@]13(O)[C@@H](OC(=O)[C@]1(O)C)C2=C([C@H](OC(=O)C(/C)=C\C)C[C@@H]2[C@@](OC(=O)C)(C[C@@H]3OC(=O)[C@H](CC)C)C)C
• InChI: 1S/C27H38O10/c1-9-13(3)22(29)34-18-11-17-20(15(18)5)21-27(33,26(8,32)24(31)36-21)19(35-23(30)14(4)10-2)12-25(17,7)37-16(6)28/h9,14,17-19,21,32-33H,10-12H2,1-8H3/b13-9-/t14-,17-,18+,19-,21-,25-,26+,27+/m0/s1
• InChIKey: FIAZIVNRHQWTPY-QAAPNFDWSA-N

Properties

• Density: 1.272g/cm³ (Cal.)
• Boiling point: 602.227°C at 760 mmHg (Cal.)
• Flash point: 190.24°C (Cal.)

References

• (1): Andrews Stephen P., Ball Matthew, Wierschem Frank, Cleator Ed, Oliver Steven, Högenauer Klemens, Simic Oliver, Antonello Alessandra, Hünger Udo, Smith Martin D., Ley Steven V.. Total Synthesis of Five Thapsigargins: Guaianolide Natural Products Exhibiting Sub-Nanomolar SERCA Inhibition, Chemistry - A European Journal, 2007