Farnesol
Structural formula | |||||||||||||||||||
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(2 E , 6 E ) form of farnesol | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Farnesol | ||||||||||||||||||
other names |
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Molecular formula | C 15 H 26 O | ||||||||||||||||||
Brief description |
colorless liquid |
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properties | |||||||||||||||||||
Molar mass | 222.37 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
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density |
0.89 g cm −3 |
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boiling point | |||||||||||||||||||
solubility |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Farnesol is an acyclic sesquiterpene alcohol with a floral odor reminiscent of lily of the valley . The name comes from the acacia species Acacia farnesiana . Farnesol is a juvenile hormone and insect pheromone .
Occurrence
Farnesol is common in the oil of musk grains , linden blossom and is found in other essential oils such as anise oil , jasmine oil, and rose oil .
Extraction and presentation
It can be made by acid isomerization of nerolidol , which can be synthesized from linalool through several steps :
use
It is used as a fragrance and antibacterial agent in cosmetics .
Biological importance
As a diphosphate (also known as farnesyl pyrophosphate , FPP), farnesol is an important intermediate product in metabolism. It plays a central role in the prenylation of proteins , in the biosynthesis of cholesterol , ubiquinone and other terpenes and is itself formed from geranyl diphosphate (GPP, see also geraniol ). Farnesol inhibits hyphae growth in the dimorphic fungus Candida albicans and is also referred to as a quorum sensing molecule in this context .
Medical application
Farnesol inhibits the formation of staphylococci - and streptococci - biofilms . Farnesol also degrades the enzymes farnesyl transferase and fatty acid synthase , which is why it could be used in cancer therapy.
Individual evidence
- ↑ a b entry on Farnesol. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
- ↑ a b c d Entry on Farnesol in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
- ↑ Entry on Farnesol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ↑ Juliane Daphi-Weber, Heike Raddatz, Rainer Müller: Investigation of Fragrances - Controlled Fragrances , pp. 94–95, in Volume V of the series HighChem hautnah - News from food chemistry (published by the Society of German Chemists ) 2010, ISBN 978- 3-936028-64-5 .
- ↑ Robin E. Duncan, Michael C. Archer: Farnesol decreases serum triglycerides in rats: identification of mechanisms including up-regulation of PPARalpha and down-regulation of fatty acid synthase in hepatocytes . In: Lipids . tape 43 , no. 7 , July 2008, p. 619-627 , doi : 10.1007 / s11745-008-3192-3 , PMID 18509688 .