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16-O-Methyl-cafestol.

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    A novel compound, (3bS,5aS,7R,8R,10aR,10bS)-7-meth-oxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodeca-hydro-5a,8-methano-5aH-cyclo-hepta-l[5,6]naph-tho[2,1-b]furan-7-methanol, was isolated from Coffea robusta beans. Its crystal structure reveals five fused rings and intermolecular hydrogen bonding.

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    Area of Science:

    • Natural Product Chemistry
    • Organic Chemistry
    • Crystallography

    Background:

    • Coffea robusta beans are a source of diverse chemical compounds.
    • Understanding the chemical constituents of coffee is important for various applications.

    Purpose of the Study:

    • To isolate and characterize a novel compound from Coffea robusta beans.
    • To elucidate the molecular structure and crystal packing of the isolated compound.

    Main Methods:

    • Isolation of the title compound from Coffea robusta bean extract.
    • Spectroscopic analysis for structural determination.
    • X-ray crystallography for crystal structure analysis.

    Main Results:

    • The novel compound (3bS,5aS,7R,8R,10aR,10bS)-7-meth-oxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodeca-hydro-5a,8-methano-5aH-cyclo-hepta-l[5,6]naph-tho[2,1-b]furan-7-methanol (C21H30O3) was successfully isolated.
    • The molecule features a complex structure with five fused rings, including a furan ring.
    • Crystal structure analysis revealed specific ring conformations and the presence of intermolecular O-H⋯O hydrogen bonding.

    Conclusions:

    • The study successfully identified and characterized a new chemical entity from Coffea robusta.
    • The detailed structural information provides insights into the stereochemistry and intermolecular interactions of this natural product.
    • This finding contributes to the chemical knowledge base of Coffea species.