Cafestol

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of Cafestol
General
Surname Cafestol
other names
  • Cafesterol
  • Coffeol
  • (3b S , 5a S , 7 R , 8 R , 10a R , 10b S ) -3b, 4,5,6,7,8,9,10,10a, 10b, 11,12-dodecahydro-7-hydroxy- 10b-methyl-5a, 8-methano-5a H -cyclohepta [5,6] naphtho [2,1- b ] furan-7-methanol
Molecular formula C 20 H 28 O 3
Brief description

colorless, crystalline solid

External identifiers / databases
CAS number
PubChem 108052
Wikidata Q423829
properties
Molar mass 316.44 g mol −1
Physical state

firmly

Melting point

160-162 ° C

solubility
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cafestol is a chemical compound from the group of diterpenes .

Occurrence

Coffee bean oil is obtained from both unroasted and roasted coffee beans

Cafestol is found in the fruits of the coffee plant . Coffea arabica varieties contain 2.7–6.7 g / kg in the dry matter, Coffea robusta beans 1.5–3.7 g / kg. The terpene is present in the fruit as an ester with fatty acids , mostly as cafestol palmitate or behenic acid ester, and is partly released during roasting and partly broken down into dehydrocafestol and cafestal.

Although only slightly soluble in water, Cafestol is also found in coffee infusions .

Structure and properties

The main tetracyclophytanes

The chemical structure of cafestol can be described as a derivative of kauran , a tetracyclophytan , with a fused furan ring. When coffee was first isolated from oily components of coffee in the 1930s , cafestol was initially mistaken for a steroid and was therefore called cafesterol . In the presence of acids, the terpene decomposes rapidly; The waxy to crystalline fatty acid esters in Cafestol are also sensitive to acids and tend to polymerize spontaneously . With antimony (III) chloride and phosphomolybdic acid , the terpene and its esters show a characteristic color reaction that can be used for detection.

The kahweol or 1,2-dehydrocafestol

Another derivative of cafestol found in coffee is kahweol ( 1,2-dehydrocafestol ).

Use and biological effect

Coffee bean oil , which contains 15% cafestol and kahweol, was used as a sunscreen . Both substances showed anti-inflammatory, anti- genotoxic and anti- carcinogenic properties; in rats they prevented the formation of breast carcinomas , in golden hamsters various tumors were inhibited by up to 40%. The effect is attributed to an activation of glutathione-S-transferase .

Cafestol inhibits the enzymes cholesterol-7-hydroxylase and sterol-27-hydroxylase in the hepatocytes , which are necessary for the breakdown of cholesterol into bile acids and thus indirectly increases the cholesterol level , in particular of so-called LDL cholesterol , which is a risk factor for the cardiovascular system -Diseases applies. When consuming coffee, this effect can be minimized by using paper filters which, due to their fine-pored structure, hold back a large part of the cafestol.

Cafestol is commercially available, inter alia, in the form of cafestol acetate or 16- O -methylcafestol .

Individual evidence

  1. ↑ a b Shmuel Yannai: Dictionary of food compounds with CD-ROM: additives, flavors and ingredients. CRC Press, 2004, ISBN 978-1-58488-416-3 , p. 147.
  2. ↑ a b c Entry on Cafestol. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
  3. ↑ a b Science Online Lexica: Entry on Cafestol in the Lexicon of Nutrition. Retrieved November 5, 2009.
  4. ^ A b Richard E. McDonald, Magdi M. Mossoba: New techniques and applications in lipid analysis. The American Oil Chemists Society, 1997, ISBN 978-0-935315-80-6 , pp. 358-359.
  5. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  6. ^ A b Robert Hegnauer: Chemotaxonomy of plants: An overview of the distribution and the systematic importance of plant substances. Volume 21, Birkhäuser, 1973, ISBN 978-3-7643-0667-0 , p. 169.
  7. ↑ National Toxicology Program (NTP): Cafestol (CASRN 469-83-0) and Kahweol (CASRN 6894-43-5) - Review of Toxicological Literature. ( Memento from May 29, 2016 in the Internet Archive ) (PDF; 890 kB), October 1999.
  8. ^ Rob M. van Dam: Coffee Consumption and Coronary Heart Disease: Paradoxical Effects on Biological Risk Factors versus Disease Incidence . 2008, doi : 10.1373 / clinchem.2008.111542 .
  9. ↑ Data sheet 2,3-cafestol acetate from Sigma-Aldrich , accessed on September 27, 2013 ( PDF ).
  10. ↑ Data sheet 16-O-Methylcafestol from Sigma-Aldrich , accessed on September 27, 2013 ( PDF ).