Cafestol

• Cafesterol
• Coffeol

• 469-83-0
• 81760-48-7 (acetate )

Colorless, crystalline solid

Fixed

160-162 ° C

• Slightly soluble in water and petroleum ether
• Soluble in diethyl ether, acetone and chloroform

Template: Infobox chemical / molecular formula search available

Cafestol is a chemical compound from the group of diterpenes, which occurs naturally in the fruit of the coffee plant. Coffea arabica - varieties contain at 2.7 to 6.7 g / kg of dry matter, Coffea robusta beans 1.5-3.7 g / kg. The terpene is present in the fruit as esters with fatty acids before, mostly as Cafestolpalmitat or behenic acid, and is partly released during roasting, partly decomposed to Dehydrocafestol and Cafestal. Although only slightly soluble in water, cafestol is also found in coffee infusion.

Structure and Properties

The chemical structure of the cafestol may be described as having a fused furan ring as a derivative of Kauran, a Tetracyclophytan. The first isolation of oily components of coffee in the 1930s cafestol was initially mistaken for a steroid and therefore referred to as Cafesterol. In the presence of acids, the terpene rapidly decomposed; the waxy to crystalline fatty acid esters of cafestol are acid sensitive and tend to spontaneous polymerization. Antimony (III ) chloride and phosphomolybdic acid, and the terpene esters thereof show a characteristic color reaction which can be used for detection.

One also found in coffee derivative of cafestol is the kahweol (1,2- Dehydrocafestol ).

Use and biological effect

Coffee bean oil, which contains cafestol and kahweol of 15%, was used as a sunscreen. Both compounds showed anti-inflammatory, and anticarcinogenic properties antigenotoxic; in rats in preventing the formation of mammary carcinomas, tumors in hamsters different by up to 40 % have been inhibited. The effect is attributed to the activation of glutathione-S- transferase. Cafestol inhibits the enzymes cholesterol 7- hydroxylase and the sterol 27- hydroxylase in the hepatocytes that are required for the reduction of cholesterol to bile acids and thus indirectly increases the level of cholesterol.

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