Farnesol

Structural formula
	(2 E , 6 E ) form of farnesol
General
Surname	Farnesol
other names	3,7,11-trimethyl-2,6,10-dodecatrien-1-ol; (2 E , 6 E ) -3,7,11-trimethyl-2,6,10-dodecatrien-1-ol;
Molecular formula	C 15 H 26 O
Brief description	colorless liquid
External identifiers / databases
EC number	225-004-1
ECHA InfoCard	100.022.731
PubChem	3327
DrugBank	DB02509
Wikidata	Q60194891
properties
Molar mass	222.37 g mol −1
Physical state	liquid
density	0.89 g cm −3
boiling point	155–157 ° C (16 h Pa )
solubility	almost insoluble in water * soluble in diethyl ether and THF ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-317-319
	P: ?
Toxicological data	6000 mg kg −1 ( LD 50 , rat , oral )
	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

Rose 'Rose de Meaux'.

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 .

It can be made by acid isomerization of nerolidol , which can be synthesized from linalool through several steps :

Isomerization of nerolidol to farnesol.

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

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 .

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.

↑ ^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 .