Description
Farnesol has a characteristic flowery odor.
Chemical Properties
Farnesol is a component of
many blossom oils. It is a colorless liquid with a linden blossom odor, which
becomes more intense when evaporated.
Of the four possible isomers (due to the double bonds in the 2- and 6-positions),
the (2E,6E)-isomer is the most common in nature and occurs, forexample, in ambrette seed oil.(2Z,6E)-Farnesol [3790-71-4] has been
identified in petitgrain oil bigarade.
Synthetic farnesol is a mixture of isomers obtained by isomerization of nerolidol.
Farnesol is particularly suited for use in flower compositions and is valued for
its fixative and deodorizing properties.
Chemical Properties
Farnesol has a characteristic fowery odor The physical constants vary slightly, depending on the source and the method of preparation.
Chemical Properties
colourless liquid with a floral odour
Occurrence
The presence of this terpene alcohol in nature has been reported in more than 30 essential oils; the levels are generally low (0.5 to 1.0%) with the exception of cabreuva, which contains up to 2 5% farensol, and the distillate from fowers of Oxystigma buccholtzii Harms which contains up to 18% farnesol Among the essential oils containing farnesol are lemongrass, Ceylon citronella, cananga, ambrette seeds, ylang-ylang, Acacia farnesiana, Peru balsam, palmarosa, tuberose, and others Reported found in apricot, citrus peel oils, grapefruit juice, strawberry jam, ginger, clove bud, hop oil, cardamom, ginger, thyme, beer, whiskey, basil, papaya, anise seed, German chamomile and Cympogon citratus oils
Uses
It can be used to induce apoptosis in cell cultures. It is also used as an antimicrobial agent. It is used in perfumes and as a flavoring agent.
Uses
antineoplastic, antibacterial
Uses
farnesol is described as a substance of high biological potential, capable of acting in the skin as a true bioactivator. A biological precursor and fatty alcohol, farnesol is one component of vitamin K. It is said to help smooth wrinkles, normalize sebum secretion, and increase the skin’s elasticity, tissue tension, and moisture-binding capability. It is able to penetrate the epidermis. In humans, farnesol is found in the skin and is involved in sterol biosynthesis. It is also used for its deodorant, odor-masking, and skin-soothing properties. In clinical studies, farnesol has demonstrated anti-microbial activity, though it is unclear if this remains the case once incorporated into a cosmetic formulation. It is widely present in vegetables and found in many essential oils (for example, acacia, lilac, lily of the valley, rose, orange blossom, oak moss, and sandalwood).
Definition
ChEBI: A farnesane sesquiterpenoid that is dodeca-2,6,10-triene substituted by methyl groups at positions 3, 7 and 11 and a hydroxy group at position 1.
Preparation
One method uses cabreuva as the starting material (Swiss Patent 261,120-Givaudan and Co ), while a second method starts from ambrette seeds (German Patent 149, 603-Haarmann and Reimer).
Aroma threshold values
Detection: 1 ppm; aroma characteristics at 1.0%: foral rose, sweet, fruity linalool with a fusel alcoholic, green lavender and haylike nuances.
Taste threshold values
aste characteristics at 10 ppm: sweet foral, fruity apricot and peachlike, green with woody tea and grape nuances.
General Description
Colorless liquid with a delicate floral odor.
Reactivity Profile
Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Contact allergens
Farnesol is one of the most frequent contact allergens
in perfumes. It is contained in small amounts in
Myroxylon pereirae and poplar buds. It is a blend of
four diastereosiomers trans/cis. As a fragrance allergen,
farnesol has to be mentioned by name in cosmetics
within the EU.
Biochem/physiol Actions
Taste at 10 ppm
Anticancer Research
A pharmacogenomic approach was used for the farnesol. Tests on many genesinvolved in apoptosis, regulation of transcription, and genes like INE1, CTRL,MRS2, NEB, LMO7, C9orf3, and EHBP1 are not conferred resistance to farnesol.The effects of farnesol on genes not related to the resistance to anticancer drugs mayspeculate the design of new drugs against tumor-resistant line (Manjamalai andGrace 2012a, 2012b; Ji et al. 2014).
Purification Methods
The main impurity is the cis-trans isomer. Purify it by gas chromatography using a 4ft x 0.125in 3%OV-1 column at 150o. [Corey et al. J Am Chem Soc 92 6637 1970, Popjak et al. J Biol Chem 237 56 1962.] It has also been fractionated through a 14-in Podbielniak column (p 11) at 11o/0.35mm. Alternatively it has been purified by gas chromatography using SF96 silicone on Fluoropak columns or Carbowax 20M on Fluoropak or base-washed 30:60 firebrick (to avoid decomposition, prepared by treating the firebrick with 5N NaOH in MeOH and washed with MeOH to pH 8) at 210o with Helium carrier gas at 60 mL/min flow rate. The diphenylcarbamoyl derivative has m 61-63o (from MeOH) and has an IR band at 3500 cm-1. [Bates et al. J Org Chem 28 1086 1963, Beilstein 1 IV 2335.]
