|3D model (Jmol)||Interactive image|
|Molar mass||154.25 g/mol|
|Density||0.858 – 0.868 g/cm3|
|Melting point||< −20 °C (−4 °F; 253 K)|
|Boiling point||198 to 199 °C (388 to 390 °F; 471 to 472 K)|
|Flash point||55 °C (131 °F; 328 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Linalool (/, , , , / or //) is two enantiomers naturally occurring terpene alcohol chemicals found in many flowers and spice 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 β-linalool, linalyl alcohol, linaloyl oxide, p-linalool, allo-ocimenol, and 3,7-dimethyl-1,6-octadien-3-ol.
Over 200 species of plants produce linalool, mainly from the families Lamiaceae (mint and other herbs), Lauraceae (laurels, cinnamon, rosewood), and Rutaceae (citrus fruits), but also birch trees and other plants, from tropical to boreal climate zones. It has also been found in some fungi and cannabis.
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) seed, palmarosa [Cymbopogon martinii var martinii (Roxb.) Wats., family Poaceae], and sweet orange (Citrus sinensis Osbeck, family Rutaceae) flowers. (R)-linalool is present in lavender (Lavandula officinalis Chaix, family Lamiaceae), bay laurel (Laurus nobilis, family Lauraceae), and sweet basil (Ocimum basilicum, family Lamiaceae), among others.
Each enantiomer evokes different neural responses in humans, and therefore are classified as possessing distinct scents. (S)-(+)-Linalool is perceived as sweet, floral, petitgrain-like (odor threshold 7.4 ppb) and the (R)-form as more woody and lavender-like (odor threshold 0.8 ppb).
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.
Linalool is used in some mosquito-repellent products; however, the EPA notes that "a preliminary screen of labels for products containing [l]inalool (as the sole active ingredient) indicates that efficacy data on file with the Agency may not support certain claims to repel mosquitos."
Stress relief in rodents
Akio Nakamura and colleagues from the University of Tokyo and T. Hasegawa Co., Ltd in Kawasaki, Japan, claim to have demonstrated that inhaling linalool can reduce stress in lab rats. In a study published in The Journal of Agriculture and Food Chemistry, they exposed the animals to stressful conditions and found that those inhaling linalool saw their stress-elevated levels of neutrophils and lymphocytes fall to near-normal levels compared with the controls. Inhaling linalool also reduced the activity of more than 100 genes that "go into overdrive" in stressful situations. The findings could form the basis of new blood tests for identifying fragrances that can soothe stress, the researchers claim.
Plants that contain linalool
- Cinnamomum tamala
- Cannabis sativa
- Cannabis indica
- Ocimum basilicum
- Solidago Meyen, Solidago chilensis
- Artemisia vulgaris (mugwort)
- Humulus lupulus
Linalool gradually breaks down when in contact with oxygen, forming an oxidized by-product that may cause allergic reactions such as eczema in susceptible individuals. Between 5 and 7% of patients undergoing patch testing in Sweden were found to be allergic to the oxidized form of linalool.
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