Cafestol

Cafestol

Names
IUPAC name (3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b,11,12-Dodecahydro-7-hydroxy-10b-methyl-5a,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
Identifiers
CAS Number	469-83-0
3D model (Jmol)	Interactive image
ChemSpider	10289419
KEGG	C09066
PubChem CID	108052
UNII	AC465T6Q6W
InChI InChI=1/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13?,15-,17+,18-,19+,20+/m1/s1 Key: DNJVYWXIDISQRD-GTATUSGQBK
SMILES OC[C@@]5(O)C[C@@]31C[C@@H]5CC[C@H]1[C@]4(C)CCc2occc2[C@H]4CC3
Properties
Chemical formula	C20H28O3
Molar mass	316.44 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).
Infobox references

Cafestol is a diterpene molecule present in coffee.

A typical bean of Coffea arabica contains about 0.4-0.7% cafestol by weight. Cafestol is present in highest quantity in unfiltered coffee drinks such as French press coffee or Turkish coffee/Greek coffee. In filtered coffee drinks such as drip brewed coffee, it is present in only negligible amounts.

Studies have shown that regular consumption of boiled coffee increases serum cholesterol by 8% in men and 10% in women. For those drinking filter coffee, the effect was only significant for women.

Cafestol has also shown anticarcinogenic properties in rats. Cafestol may act as an agonist ligand for the nuclear receptor farnesoid X receptor and pregnane X receptor, blocking cholesterol homeostasis. Cafestol also has neuroprotective effects in a Drosophila fruit fly model of Parkinson's disease.