Cafestol

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Cafestol
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
PubChem 108052
ChemSpider 10289419
UNII AC465T6Q6W
KEGG C09066
Jmol-3D images {{#if:OC[C@@]5(O)C[C@@]31C[C@@H]5CC[C@H]1[C@]4(C)CCc2occc2[C@H]4CC3|Image 1
Properties
Molecular formula C20H28O3
Molar mass 316.43 g mol−1
Melting point 158 to 162 °C; 316 to 324 °F; 431 to 435 K
Except where noted otherwise, 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 0.6% 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.[1]

Potential biological activity

Cafestol has also shown anticarcinogenic properties in rats.[1] Cafestol may act as an agonist ligand for the nuclear receptor farnesoid X receptor and pregnane X receptor, blocking cholesterol homeostasis.[2] Cafestol also has neuroprotective effects in a Drosophila fruit fly model of Parkinson's disease.[3] Cafestol and kahweol from coffee extracts have been claimed as beneficial in the treatment of mesothelioma.[4]

See also

References

  1. ↑ 1.0 1.1 National Toxicology Program (NTP): Cafestol (CASRN 469-83-0) and Kahweol (CASRN 6894-43-5) - Review of Toxicological Literature. (PDF) October 1999
  2. ↑ Ricketts ML, Boekschoten MV, Kreeft AJ, Hooiveld GJ, Moen CJ, Müller M, Frants RR, Kasanmoentalib S, Post SM, Princen HM, Porter JG, Katan MB, Hofker MH, Moore DD (July 2007). "The cholesterol-raising factor from coffee beans, cafestol, as an agonist ligand for the farnesoid and pregnane X receptors". Mol. Endocrinol. 21 (7): 1603–16. doi:10.1210/me.2007-0133. PMID 17456796. 
  3. ↑ Trinh K, Andrews L, Krause J, Hanak T, Lee D, Gelb M, Pallanck L (April 2010). "Decaffeinated coffee and nicotine-free tobacco provide neuroprotection in Drosophila models of Parkinson's disease through an NRF2-dependent mechanism". J. Neurosci. 30 (16): 5525–32. doi:10.1523/JNEUROSCI.4777-09.2010. PMID 20410106. Lay summary – New Scientist. 
  4. ↑ Jeong Hyeon Sim, “Cafestol and kahweol from coffee extracts for treating malignant pleural mesothelioma”, KR Patent CN 2,013,119,032 (2013)
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