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| Names | |
|---|---|
| IUPAC name (3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b-Decahydro-7-hydroxy-10b-methyl-5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| Properties | |
| C20H26O3 | |
| Molar mass | 314.425 g·mol−1 |
| Appearance | Colourless |
| Melting point | 143-143.5°C |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Kahweol is aditerpenoid molecule found in the beans ofCoffea arabica and is structurally related tocafestol.[1] It was named after theArabicقهوةqahwa meaning "coffee".[2]
Kahweol belongs to a group of organic compounds known as naphthofurans, containing bothnaphthalene andfuran moieties.[3] It is a colourless crystal at room temperature that oxidises readily and yellows within hours.[2]
Kahweol was first isolated and identified as a constituent of coffee bean oil in 1932.[2] The compound was isolated as its free "unsaponifiable" alcohol form. The solvent used greatly influences the crystal form, withacetone producing "large colorless trigonal or pentagonal dense plates,"methanol producing "massive colorless quadratic plates," and ether producing "very long, snow-white silky needles."[2]
While the presence ofesters of cafestol (ahydrogenated analogue of kahweol) were apparent since the 1960s, it was not until 1982 that kahweol was isolated as an ester of its own.[4] Following the development ofliquid chromatography-mass spectrometry in the late20th century, kahweol was isolated in other esteric forms, namelystearate,linoleate, andoleate, with minor amounts ofarachidate andbehenate.[5]
Kahweol, and its related diterpenoid cafestol, are found in all parts of the coffee plant. Transferred from the endosperm to the seedling during germination, it may have a role in defense against insects and pathogenic fungi.[6]
