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CAS NUMBER: 4602-84-0
EC NUMBER: 225-004-1
MOLECULAR FORMULA: (CH3)2C=CHCH2CH2C(CH3)=CHCH2CH2C(CH3)=CHCH2OH
MOLECULAR WEIGHT: 222.37
Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol.
Under standard conditions, Farnesol is a colorless liquid.
Farnesol is hydrophobic, and thus insoluble in water, but miscible with oils.
Farnesol is produced from 5-carbon isoprene compounds in both plants and animals. Phosphate-activated derivatives of farnesol are the building blocks of possibly all,l acyclic sesquiterpenoids.
These compounds are doubled to form 30-carbon squalene, which in turn is the precursors for steroids in plants, animals, and fungi.
As such, farnesol and its derivatives are important starting compounds for both natural and artificial organic synthesis
Farnesol is found in a flower extract with a long history of use in perfumery.
The pure substance farnesol was named (c. 1900–1905) after the Farnese acacia tree (Vachellia farnesiana), since the flowers from the tree were the commercial source of the floral essence in which the chemical was identified.
This particular acacia species, in turn, is named after Cardinal Odoardo Farnese (1573–1626) of the notable Italian Farnese family which (from 1550 though the 17th century) maintained some of the first private European botanical gardens in the Farnese Gardens in Rome.
The addition of the -ol ending results from Farnesol being chemically an alcohol.
The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.
Farnesol is used as a deodorant in cosmetic products.
Farnesol is subject to restrictions on its use in perfumery, as some people may become sensitised to it.
Farnesol is a colorless liquid with a delicate floral odor.
Farnesol is 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.
Farnesol has a role as a plant metabolite, a fungal metabolite and an antimicrobial agent.
Farnesol is a farnesane sesquiterpenoid, a primary alcohol and a polyprenol.
Farnesol is a nature identical deodorizing agent that has specific anti-bacterial activity against grampositive microbes responsible for body odor.
Farnesol Plus is a nature identical, synergistic complex of active ingredients with deodorising properties.
Farnesol Plus is composed of Farnesol, Phenoxyethanol, Glycerine monolaurate.
Farnesol is a flavor and perfume ingredient found in nature and also manufactured synthetically; associated with allergies and contact dermatitis.
Farnesol (C15H26O) is a sesquiterpene alcohol found in essential oils.
This substance is reported to have different pharmacological activities such as antimicrobial, antitumor and antioxidant effects, as well as actions in different body systems.
Farnesol, a natural sesquiterpene alcohol in essential oils, was found to have potential for alleviating massive inflammation, oxidative stress and lung injury.
However, effects of farnesol supplementation on allergic asthma remain unclear.
Farnesol was administered to OVA-sensitised and challenged mice for 5 weeks.
Three farnesol doses, namely 5, 25 and 100mg farnesol/kg BW/day, non-sensitised control, dietary control, and positive control (dexamethasone 3mg/kg BW by gavage) were included.
Sera and bronchoalveolar lavage fluids from the experimental mice were collected to measure farnesol concentrations, serum lipid profiles, antibody titres, differential cell counts or Th1/Th2 cytokines levels.
Farnesol is a natural sesquiterpene alcohol that is potent in treating antimetabolic disorders, anti-inflammation, showing antioxidant, and antibiotic effects.
Farnesol exhibits a relative Th1-inclination and anti-inflammatory property to immune cells in vitro.
Farnesol has potential for alleviating massive inflammation, oxidative stress and lung injury induced by intratracheal instillation of cigarette smoke extract in rats.
Farnesol also ameliorates 1,2-dimethylhydrazine induced oxidative stress, inflammation and apoptosis in the colon of Wistar rats.
Farnesol is a signaling molecule that is derived from farnesyl diphosphate, an intermediate in the isoprenoid/cholesterol biosynthetic pathway.
Farnesol is a 15 carbon isoprenoid alcohol is the corresponding dephosphorylated form of the isoprenoid farnesyl diphosphate.
Farnesol has a potential role in controlling the degradation of 3-hydroxy-3-methylglutaryl coenzyme A (HMGCoA) reductase (EC 1.1.1.34, NADPH-hydroxymethylglutaryl-CoA reductase).
The enzyme is stabilized under conditions of cellular sterol depletion (e.g. statin-treated cells) and rapidly degraded in sterol-loaded cells.
Farnesol is dependent on the presence of both a sterol and a non-sterol derived from the isoprenoid pathway; farnesol, the dephosphorylated form of farnesyl diphosphate, can function as the non-sterol component.
Farnesol has been shown to activate the farnesoid receptor (FXR), a nuclear receptor that forms a functional heterodimer with RXR.
Thus, dephosphorylation of farnesyl diphosphate, an intermediate in the cholesterol synthetic pathway, might produce an active ligand for the FXR:RXR heterodimer.
The physiological ligand for FXR remains to be identified; farnesol, may simply mimic the unidentified natural ligand(s).
In addition, exogenous farnesol have an effect on several other physiological processes, including inhibition of phosphatidylcholine biosynthesis, induction of apoptosis, inhibition of cell cycle progression and actin cytoskeletal disorganization.
Farnesol cellular availability is an important determinant of vascular tone in animals and humans, and provides a basis for exploring farnesyl metabolism in humans with compromised vascular function as well as for using farnesyl analogues as regulators of arterial tone in vivo.
A possible metabolic fate for farnesol is its conversion to farnesoic acid, and then to farnesol-derived dicarboxylic acids (FDDCAs) which would then be excreted in the urine.
Farnesol can also be oxidized to a prenyl aldehyde, presumably by an alcohol dehydrogenase (ADH), and that this activity resides in the mitochondrial and peroxisomal.
Farnesols are able to phosphorylate farnesol to Farnesyl diphosphate in a Cytosine triphosphate dependent fashion.
Prenol is polymerized by dehydration reactions; when there are at least four isoprene units (n in the above formula is greater than or equal to four), the polymer is called a polyprenol.
Polyprenols can contain up to 100 isoprene units (n=100) linked end to end with the hydroxyl group (-OH) remaining at the end.
These isoprenoid alcohols are also called terpenols.
These isoprenoid alcohols are important in the acylation of proteins, carotenoids, and fat-soluble vitamins A, E and K.
They are also building blocks for plant oils such as farnesol and geraniol.
Prenol is also a building block of cholesterol (built from six isoprene units), and thus of all steroids.
Prenol has sedative properities, it is probably GABA receptor allosteric modulator.
When the isoprene unit attached to the alcohol is saturated, the compound is referred to as a dolichol.
Farnesols are important as glycosyl carriers in the synthesis of polysaccharides.
Very mild and delicate green floral odour with typical lily of the valley character and excellent fixative effect on many floral notes.
Farnesol is one of the classic perfumery ingredients and is present in many flowers and herbs from orange flowers to thyme.
Once reserved only for the most expensive fragrances it became more widely available in the 1960s when synthesis methods became more cost-effective.
Farnesol is an odorous molecule that is part of the list of 26 allergens regulated by Europe.
Farnesol is present in many essential oils such as linden or acacia flowers.
Farnesol is an acrylic sesquiterpene alcohol used as a deodorizing agent and anti-aging ingredient.
Farnesol has specific antimicrobial activity against gram-positive bacteria responsible for body odor.
Farnesols deodorizing/anti-aging ingredient and substantive on the skin, making it suitable for rinse-off applications like shower gel and shampoo.
Farnesol, an alcohol found in essential oils including ambrette seed and citronella, could be a beneficial component of facial masks, according to a study published June 27 in the Journal of Cosmetic Dermatology.
Researchers in Taiwan report facial masks containing 0.3 and 0.8 mM farnesol improved skin smoothness and enhanced collagen content and arrangement in a study of rats’ skin, when the mask was applied with and after UVB exposure.
Farnesol is a fungal quorum-sensing molecule and natural sesquiterpene produced by many organisms, according to the study.
Farnesol can be found in peaches, tomatoes, lemongrass and chamomile, the authors write.
A colorless liquid extracted from oils of plants such as citronella, neroli, cyclamen, and tuberose.
Farnesol is an intermediate step in the biological synthesis of cholesterol from mevalonic acid in vertebrates.
Farnesol is a natural sesquiterpenoid and an interesting quorum-sensing molecule.
Farnesols insolubility in water is the biggest obstacle to its application for bacterial biofilm treatments since Farnesol compromises the bioavailability.
Recently, an increasing interest in farnesol encapsulation or loading in polymeric materials may be noted due to the prolonged action of the active macromolecular systems.
In this short review, we present an overview of methods leading to improved interactions between farnesol and microbial biofilms.
Farnesol combines the distinctive lightness of Gemseal® 40 with the remarkable ability of SENSANOV™ WR to disperse the mattifying charge. Moreover, it contains PIXALIA®, an active for sebum control and pore size reduction.
Farnesol is a component of many blossom oils.
Farnesol 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 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 Farnesols fixative and deodorizing properties.
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.
Farnesol is said to help smooth wrinkles, normalize sebum secretion, and increase the skin’s elasticity, tissue tension, and moisture-binding capability.
Farnesol is able to penetrate the epidermis.
In humans, farnesol is found in the skin and is involved in sterol biosynthesis.
Farnesol is also used for Farnesols 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.
Farnesol 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).
Farnesol is produced from 5-carbon isoprene compounds in both plants and animals.
Phosphate-activated derivatives of farnesol are probably the building blocks of all acyclic sesquiterpenoids.
These compounds double to form 30-carbon squalene, which are precursors to steroids in plants, animals, and fungi.
Therefore, farnesol and its derivatives are important starting compounds for both natural and artificial organic synthesis.
Farnesol is found in many essential oils such as citronella, neroli, cyclamen, lemongrass, tuberose, rose, musk, balsam and tolu.
Farnesol is used in perfumery to accentuate the scents of sweet, floral perfumes.
Farnesol increases the fragrance of perfume by acting as a co-solvent regulating the volatility of fragrance substances.
Farnesol is especially used in lilac perfumes.
Farnesol has been suggested that Farnesol functions as a chemopreventive and anti-tumor agent.
Farnesol is used as a deodorant in cosmetic products due to Farnesols antibacterial effect.
Farnesol is subject to restrictions on its use in perfumery, as some people may be sensitized to it, but the evidence that farnesol can cause an allergic reaction in humans is controversial.
In one study, researchers found that in a tissue culture, Peru Balsam and farnesol were able to bind to CD1a molecules on the surface of Langerhans cells and activated T cells.
However, researcher de Jong said, "Our work shows how these chemicals can activate T cells in tissue culture, but we must be careful to claim that this certainly works in allergic patients.
The study paves the way for follow-up studies to confirm the mechanism in allergic patients and design inhibitors of the response."
Despite this caveat, some popular sciences have accepted the preliminary findings of this study as conclusive evidence that farnesol induces an immunological response through this mechanism.
Farnesol has an appearance of a colourless to yellowish, clear liquid used in deodorants.
In addition to the natural deodorant properties of Farnesol, it also acts as a natural Preservative booster allowing for the formulation of milder and more skin sensitive deodorants.
Farnesol selectively inhibits gram-positive bacteria responsible for the decomposition of sweat.
In addition Farnesol shows good activity against acne causing bacteria.
Farnesol has a low and pleasant odour, comes in easy to formulate liquid and has excellent biodegradability.
Farnesol deposits on human skin, even when used in a rinse off formulation and therefore has an active deodorising effect in Shower Gels and Body Wash products.
Due to Farnesol depositing on the skin, Farnesol is effective when used in Face Washes designed to protect against acne causing Propionibacterium acnes and dermatophytes.
Farnesol is a naturally occurring sequiterpene alcohol found in various essential oils such as neroli, citronella or lemongrass.
The name comes from Acacia Farnesiana as Farnesol is a main constituent of the sweet-scented pretty flowers of this tree.
Farnesol has long been known for its remarkable purifying, anti-bacterial activity.
Derived from its centennial expertise in natural perfumery andchemistry, Farnesol is a pure nature-identical molecule that has been the product reference in the cosmetic industry for many years.
Combining high selectivity with outstanding deodorant efficacy Farnesol provides formulators with an efficient and reliable solution at very low use levels.
USES:
Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam, and tolu.
Farnesol is used in perfumery to emphasize the odors of sweet, floral perfumes.
Farnesol enhances perfume scent by acting as a co-solvent that regulates the volatility of the odorants.
Farnesol is especially used in lilac perfumes.
Farnesol is a natural pesticide for mites and is a pheromone for several other insects.
In a 1994 report released by five top cigarette companies, farnesol was listed as one of 599 additives to cigarettes.
Farnesol is a flavoring ingredient.
Farnesol contains at least 85 % of d,l-alpha-bisabolol, a monocyclic unsaturated sesquiterpene alcohol.
Ingredients of secondary importance are mainly farnesol isomers.
Farnesol has been shown to possess soothing properties for stressed and sensitive skin. Moreover, body odor control effectiveness has been demonstrated both for d,l-alpha-bisabolol and for Dragosantol®.
Farnesol is suitable for use in cosmetic products due to its stability and good compatibility to the skin.
The main areas of application for Farnesol are skin care cosmetic preparations, in particular lotions and creams for sensitive skin.
Unlike Azulen or camomile oil, Farnesol does not alter Farnesols color after long storage periods nor diffuse through plastic containers; therefore Farnesol can be used without problems.
-Flavoring effect
-flavor fixer
-skin cleaning
-softens and revitalizes skin
-disinfectant
SOURCES:
Farnesol is produced from isoprene compounds in both plants and animals.
When geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate, which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene.
Farnesol can then provide sesquiterpenoids such as farnesol.
PROPERTIES:
-Quality Level: 100
-assay: 95%
-refractive index: n20/D 1.489 (lit.)
-bp: 149 °C/4 mmHg (lit.)
-density: 0.886 g/mL at 20 °C (lit.)
-SMILES string: CC(C)=CCCC(C)=CCCC(C)=CCO
-InChI: 1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+
-InChI key: CRDAMVZIKSXKFV-YFVJMOTDSA-N
CHEMICAL PROPERTIES:
-Molecular Weight: 222.37
-Formula: C15H26O
-Density: 0.886 g/mL at 20 °C
-CAS No.: 4602-84-0
-Storage: 2 years -20°C(in the dark) liquid
-Smiles: CC(=CCCC(=CCCC(=CCO)C)C)C
FUNCTIONS:
-fragrance ingredient
-deodorant
-masking
-solvent
-soothing
SYNONYM:
(E,E)-Farnesol
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
trans-Farnesol
(2E,6E)-Farnesol
4602-84-0
2-trans,6-trans-Farnesol
All-trans-Farnesol
Farnesyl alcohol
3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
FCI 119a
Inhibitor A2
(E)-farnesol
HSDB 445
2,6-Di-trans-Farnesol
2,6,10-dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)-
(2-trans,6-trans)-farnesol
2E,6E-farnesol
Farnesol (mixture of isomers)
UNII-X23PI60R17
3,7,11-Trimethyl-2,6,10-dodecatrienol
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-
Farnesol, mixture of isomers
Floral Green
CHEBI:16619
3,7,11-trimethyldodeca-2,6,10-trien-1-ol
X23PI60R17
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-
ST072172
Farnesol 97+% FCC
(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
trans,trans-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
MFCD00002918
