Farnesol

Colorless liquid

Liquid

0.89 g · cm -3

155-157 ° C ( 16 hPa)

• Insoluble in water
• Soluble in diethyl ether and THF

6000 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Farnesol is an acyclic sesquiterpene alcohol with a flowery, reminiscent of lily of the valley odor. The name comes from the acacia Acacia farnesiana. Farnesol is an insect hormone and insect pheromone.

Occurrence

Farnesol is common in the oil of musk seeds, lime blossom and occurs in other essential oils such as anise oil, jasmine oil and rose oil.

Production and representation

It may be prepared by acidic isomerization of nerolidol, which can be synthesized in several steps from Linalool:

Use

It is used as a fragrance and antibacterial agent in cosmetics.

Biological Significance

Farnesol is as diphosphate (also farnesyl pyrophosphate, FPP, called ) is an important intermediate product of metabolism. It plays in the prenylation of proteins in the biosynthesis of cholesterol, ubiquinone and other terpenes a central role and is even from geranyl diphosphate (GPP, see also geraniol ) was formed. In the dimorphic fungus Candida albicans farnesol inhibits hyphal growth and is referred to in this context as quorum sensing molecule.

Medical Application

Farnesol inhibits the formation of staphylococcal and streptococcal biofilms. Even degrades the enzymes farnesyl farnesol and fatty acid synthase, and therefore it could be used in cancer therapy.