Kahweol

Rod-shaped crystals

Fixed

88-90 ° C

Soluble in acetone

Template: Infobox chemical / molecular formula search available

Kahweol, 1,2- Dehydrocafestol, is a chemical compound from the group of diterpenes, which occurs naturally in the fruit of the coffee plant. Coffea arabica - varieties contain at approximately 3 g / kg in the dry matter, Coffea robusta beans in some cases only traces, maximum 2 g / kg.Das terpene lies in the fruits as esters with fatty acids before, mostly as palmitate or behenic acid. Kahweol is additionally formed during roasting from the cafestol contained in higher amounts, partly decomposed, and is also found in coffee infusion.

Structure and Properties

The chemical structure of the kahweol can be described as having a fused furan ring as a derivative of Kauran, a Tetracyclophytan. Kahweol is a strong oxidizing agent, which can release the heat of carbon monoxide and carbon dioxide. It is extremely sensitive to acids.

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 on activation of glutathione -S-transferase zurückgeführt.Analog related to cafestol inhibits kahweol very likely also the enzymes cholesterol 7- hydroxylase and the sterol 27- hydroxylase in the hepatocytes that required for the reduction of cholesterol to bile acids are, and thus indirectly increases the cholesterol level.