Farnesol is a natural organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 which is an acyclic sesquiterpene

Terpene

Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium. They are often strong smelling and thus may have had a protective...

 alcohol found as a colorless liquid. It is insoluble in water, but miscible with oils. It is the building block of most, and possibly all, acyclic sesquiterpenoids and is an important starting compound for organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...

.

Uses

Farnesol is present in many essential oil

Essential oil

An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...

s such as citronella

Citronella oil

Citronella oil is one of the essential oils obtained from the leaves and stems of different species of Cymbopogon. The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol and geraniol...

, neroli

Neroli

Neroli oil is a plant oil produced from the blossom of the bitter orange tree . Its scent is sweet, honeyed and somewhat metallic, whereas bergamot, being rich in linalool , has more of an aromatic, soft, floralcy.- Production :The blossoms are gathered, usually by hand, in late April to...

, cyclamen

Cyclamen

Cyclamen is a genus of 23 species of perennials growing from tubers, valued for their flowers with upswept petals and variably patterned leaves...

, lemon grass, tuberose

Tuberose

The tuberose is a perennial plant related to the agaves, extracts of which are used as a middle note in perfumery. The common name derives from the Latin tuberosa, meaning swollen or tuberous in reference to its root system. It consists of about 12 species...

, rose

Rose

A rose is a woody perennial of the genus Rosa, within the family Rosaceae. There are over 100 species. They form a group of erect shrubs, and climbing or trailing plants, with stems that are often armed with sharp prickles. Flowers are large and showy, in colours ranging from white through yellows...

, musk

Musk

Musk is a class of aromatic substances commonly used as base notes in perfumery. They include glandular secretions from animals such as the musk deer, numerous plants emitting similar fragrances, and artificial substances with similar odors. Musk was a name originally given to a substance with a...

, balsam

Balsam

Balsam is a term used for various pleasantly scented plant products, and the plants which produce them. Balsams are oily or gummy oleoresins, usually containing benzoic acid or cinnamic acid, obtained from the exudates of various trees and shrubs and used as a base for some botanical medicines...

 and tolu

Tolu balsam

Tolu balsam or balsam of Tolu is the resinous secretion of Myroxylon balsamum.The resin is still used in certain cough syrup formulas. However its main use in the modern era is in perfumery, where it is valued for its warm, mellow yet somewhat spicy scent. It is also used as a natural remedy for...

. It is used in perfumery to emphasize the odors of sweet floral perfumes. Its method of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes.

Farnesol is a natural pesticide for mites

MITES

MITES, or Minority Introduction to Engineering and Science, is a highly selective six-week summer program for rising high school seniors held at the Massachusetts Institute of Technology. Its purpose is to expose students from minority, or otherwise disadvantaged backgrounds, to the fields of...

 and is a pheromone

Pheromone

A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

 for several other insects.

In a 1994 report released by five top cigarette companies, farnesol was listed as one of 599 additives to cigarettes. It is a flavoring ingredient.

History of the name

Farnesol is found in a flower extract with a long history of use in perfumery. The pure substance farnesol was named (ca. 1900-1905) after Farnese acacia tree (Vachellia farnesiana). The flowers from the tree were the commercial source of the floral essence. 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 it being chemically an alcohol

Alcohol

In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

. The plant itself was brought to the Farnese gardens from the Caribbean and Central America, where it originates.

Health effects

Farnesol has been suggested to function as a chemopreventative and anti-tumor agent. Farnesol is used as a deodorant in cosmetic products because of its anti-bacterial activity. Farnesol should be avoided by people with perfume allergy.

See also

• Farnesylation
• Farnesene
  Farnesene
  The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is...
  
  
• Farnesyl pyrophosphate
  Farnesyl pyrophosphate
  Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes, terpenoids, and sterols...
  
  
• Geranylgeraniol
  Geranylgeraniol
  Geranylgeraniol is a diterpene alcohol which plays a role a several important biological processes. It is an intermediate in the biosynthesis of other diterpenes and of vitamins E and K. It also used in the post-translational modification known as geranylgeranylation...
  
  
• Nerolidol
  Nerolidol
  Nerolidol, also known as peruviol, is a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers. There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. Nerolidol is present in neroli, ginger,...