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Linalool
 
 
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Linalool is a naturally-occurring terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
 alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 chemical found in many flowers and spice
Spice

A spice is a dried seed, fruit, root, bark, leaf, or vegetable used in nutritionally insignificant quantities as a food additive for the purpose of flavor, color, or as a preservative that kills harmful bacteria or prevents their growth....
 plants with many commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness). It has other names such as ß-linalool, linalyl alcohol, linaloyl oxide, p-linalool, allo-ocimenol and 2,6-dimethyl-2,7-octadien-6-ol.

200 species of plants produce linalool, mainly from the families Lamiaceae (mints, scented herbs), Lauraceae (laurels, cinnamon, rosewood) and Rutaceae (citrus fruits), but also birch trees and other plants, from tropical to boreal climate zones.






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Encyclopedia


Linalool is a naturally-occurring terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
 alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 chemical found in many flowers and spice
Spice

A spice is a dried seed, fruit, root, bark, leaf, or vegetable used in nutritionally insignificant quantities as a food additive for the purpose of flavor, color, or as a preservative that kills harmful bacteria or prevents their growth....
 plants with many commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness). It has other names such as ß-linalool, linalyl alcohol, linaloyl oxide, p-linalool, allo-ocimenol and 2,6-dimethyl-2,7-octadien-6-ol.

In nature

Over 200 species of plants produce linalool, mainly from the families Lamiaceae (mints, scented herbs), Lauraceae (laurels, cinnamon, rosewood) and Rutaceae (citrus fruits), but also birch trees and other plants, from tropical to boreal climate zones. It was also found in some fungi.

Enantiomers

Linalool has a chiral center at C3 and therefore two stereoisomers: licareol is (R)-(+)-linalool with CAS No. 126–90–9 (PubChem 67179) and coriandrol is (S)-(–)-linalool with CAS No. 126–91–0 (PubChem 13562).

Both enantiomeric forms are found in nature: S-linalool is found, for example, as a major constituent of the essential oils of coriander (Coriandrum sativum L. family Apiaceae
Apiaceae

The Apiaceae or Umbelliferae is a family of usually aromatic plants with hollow stems, commonly known as umbellifers. It includes cumin, parsley, carrot, coriander/cilantro, dill, caraway, fennel, parsnip, celery, Queen anne's lace and other relatives....
) seed, palmarosa [Cymbopogon martinii var martinii (Roxb.) Wats., family Poaceae
Poaceae

Poaceae or Gramineae is a family in the Class Liliopsida of the Magnoliophyta. Plants of this family are usually called grasses; the shrub- or tree-like plants in this family are called bamboo ....
], and sweet orange (Citrus sinensis Osbeck, family Rutaceae
Rutaceae

Rutaceae, commonly known as the Rue or Citrus family, is a family of plants, usually placed in the order Sapindales.Species of the family generally have flowers that divide into four or five parts, usually with strong scents....
) flowers. R-linalool is present in lavender (Lavandula officinalis Chaix, family Lamiaceae
Lamiaceae

Lamiaceae or Labiatae, also known as the mint family, is a family of plants comprising about 210 genera and some 3,500 species. It has been considered closely related to Verbenaceae but several recent phylogenetic studies have shown that numererous genera classified in Verbenaceae belong instead in Lamiaceae, whereas the core genera of...
), laurel (Laurus nobilis, family Lauraceae
Lauraceae

The Lauraceae or Laurel family comprises a group of flowering plants included in the order Laurales. The family contains about 55 genera and over 2000 species world-wide, mostly from warm or tropical regions, especially Southeast Asia and Brazil....
), and sweet basil (Ocimum basilicum, family Lamiaceae
Lamiaceae

Lamiaceae or Labiatae, also known as the mint family, is a family of plants comprising about 210 genera and some 3,500 species. It has been considered closely related to Verbenaceae but several recent phylogenetic studies have shown that numererous genera classified in Verbenaceae belong instead in Lamiaceae, whereas the core genera of...
), among others.

Each enantiomer evokes different neural responses in humans, and therefore are anthropophilically classified as possessing distinct scents. 3S-(+)-linalool is perceived as sweet, floral, petitgrain-like (odour threshold 7.4 ppb) and the 3R-form as more woody and lavender-like (odour threshold 0.8 ppb)

Biosynthesis

In higher plants linalool as other monoterpenoids is produced from isopentenyl pyrophosphate via the universal isoprenoid intermediate geranyl pyrophosphate, through a class of membrane-bound enzymes named monoterpene synthases. One of these, linalool synthase (LIS), has been reported to produce (S)-linalool in several floral tissues.

Uses

In addition to its use as a scent in domestic products such as soap, detergent, shampoo, and lotion, linalool is also used as a chemical intermediate
Reagent

A reagent or reactant is a substance or compound consumed during a chemical reaction. Solvents and catalysts, although they are involved in the reaction, are usually not referred to as reactants....
. One common downstream product of linalool is Vitamin E
Vitamin E

Vitamin E is the collective name for a set of 8 related a-, ?-, ?-, and d-tocopherols and the corresponding four tocotrienols, which are fat-soluble vitamins with antioxidant properties....
. Linalool, is also used by pest professionals as a flea, and cockroach insecticide

Safety information

Linalool should be avoided by people with perfume allergy.

General references

  • Casabianca H, Graff JB, Faugier V, Fleig F, Grenier C (1997) Enantiomeric distribution studies of linalool and linalyl acetate. A powerful tool for authenticity control of essential oils. HRC J High Res Chrom 21:107-112


  • Lewinshon E, Schalechet F, Wilkinson J, Matsui K, Tadmor Y, Nam K, Amar O, Lastochkin E, Larkov O, Ravid U, Hiatt W, Gepstein S, Pichersky E (2001) Enhanced levels of the aroma and flavor compound S-linalool by metabolic engineering of the terpenoid pathway in tomato fruits. Plant Physiol 127:1256–1265


  • Pengelly, Andrew. The Constituents of Medicinal Plants. 2nd Ed. 2004. CABI Publishing, U.S.A. and UK.


  • Raguso RA, Pichersky E (1999) A day in the life of a linalool molecule: chemical communication in a plant-pollinator system. Part 1: linalool biosynthesis in flowering plants. Plant Species Biol 14:95-120


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