Cafestol
Chemical compound
From Wikipedia, the free encyclopedia
Cafestol is a diterpenoid molecule present in coffee beans. It is one of the compounds that may be responsible for proposed biological and pharmacological effects of coffee.[1]
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| Names | |
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| IUPAC name
3,18-(Epoxymetheno)-19-nor-5β,8α,9β,10α,13β,16β-kaur-3-ene-16α,17-diol | |
| Systematic IUPAC name
(3bS,5aS,7R,8R,10aR,10bS)-7-(Hydroxymethyl)-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-ol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H28O3 | |
| Molar mass | 316.441 g·mol−1 |
| Melting point | 158 to 162 °C (316 to 324 °F; 431 to 435 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sources
A typical bean of Coffea arabica contains about 0.4% to 0.7% cafestol by weight.[2] Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee, and Turkish coffee. In paper-filtered coffee drinks such as drip brewed coffee, it is present in only negligible amounts, as the paper filter in drip filtered coffee retains the diterpenes.[3]
Research into biological activity
Coffee consumption has been associated with a number of effects on health and cafestol has been proposed to produce these through a number of biological actions.[4] Studies have shown that regular consumption of boiled coffee increases serum cholesterol whereas filtered coffee does not.[5] Cafestol may act as an agonist ligand for the nuclear receptor farnesoid X receptor and pregnane X receptor, blocking cholesterol homeostasis. Thus cafestol can increase cholesterol synthesis.[6]
Cafestol has also shown anticarcinogenic properties in rats.[7]
Cafestol also has neuroprotective effects in a Drosophila fruit fly model of Parkinson's disease.[8][9]