Names | |
---|---|
Preferred IUPAC name
3,7-Dimethylocta-1,6-dien-3-ol | |
Other names
3,7-Dimethyl-1,6-octadien-3-ol, β-linalool, linalyl alcohol, linaloyl oxide, allo-ocimenol, coriandrol, Licareol
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
3DMet | |
ChEBI |
|
ChEMBL |
|
ChemSpider | |
ECHA InfoCard | 100.001.032 |
KEGG | |
PubChem
CID
|
|
UNII |
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C10H18O | |
Molar mass | 154.253 g·mol−1 |
Appearance | Colorless oil |
Density | 0.858 to 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) |
1.589 g/l | |
Hazards | |
NFPA 704 (fire diamond) | |
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).
|
Linalool ( /lɪˈnæloʊɒl, laɪ-, -loʊoʊl, -ˈluːl/) refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. [1] Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness). [2] [3] A colorless oil, linalool is classified as an acyclic monoterpenoid. [1] In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. [1] Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. [1] Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate. [4]
The word linalool is based on linaloe (a type of wood) and the suffix -ol. [5] In food manufacturing, it may be called coriandrol. [1]
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.), cymbopogon ( Cymbopogon martini var. martinii), and sweet orange ( Citrus sinensis) flowers. (R)-linalool is present in lavender ( Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others.
Each enantiomer evokes distinct neural responses in humans, so each is 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).
Over 200 species of plants produce linalool, notably 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 was first synthesized in the laboratory of Leopold Ružička in 1919. [11]
In higher plants linalool is formed by rearrangement of geranyl pyrophosphate (GPP). [12] With the aid of linalool synthase (LIS), water attacks to form the chiral center. [13] [12] LIS appears to show a limonene synthase-type catalysis through a simplified "metal-cofactor-binding domain [where the majority] of the residues involved in substrate...binding [are] in the C-terminal part of the protein" suggesting stereoselectivity and the reasoning behind why some plants have varying levels of each enantiomer. [14] [15]
Linalool has complex odor and flavor properties. Its odor is similar to floral, spicy wood, somewhat resembling French lavender plants, bergamot oil or lily of the valley. [1] It has a light, citrus-like flavor, sweet with a spicy tropical accent. [1] Linalool is used as a scent in perfumed hygiene products and cleaning agents, including soaps, detergents, shampoos, and lotions. [1] [2] It exhibits antimicrobial and antifungal properties. [1] [16]
Linalool is hydrogenated to give dihydro- and tetrahydrolinalool, which are fragrances that are more resilient toward oxidants, as might be found in household cleaning products. Linalyl acetate, a popular scent, is produced by esterification of linalool (as well as occurring naturally). Isomerization of linalool gives geraniol and nerol. [17]
Linalool can be absorbed by inhalation of its aerosol and by oral intake or skin absorption, potentially causing irritation, pain and allergic reactions. [2] [18] Some 7% of people undergoing patch testing in Europe were found to be allergic to the oxidized form of linalool. [19]
The US Food and Drug Administration (FDA) lists linalool in the Code of Federal Regulations under substances generally recognized as safe, synthetic flavoring substances and adjuvants. [20]
Names | |
---|---|
Preferred IUPAC name
3,7-Dimethylocta-1,6-dien-3-ol | |
Other names
3,7-Dimethyl-1,6-octadien-3-ol, β-linalool, linalyl alcohol, linaloyl oxide, allo-ocimenol, coriandrol, Licareol
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
3DMet | |
ChEBI |
|
ChEMBL |
|
ChemSpider | |
ECHA InfoCard | 100.001.032 |
KEGG | |
PubChem
CID
|
|
UNII |
|
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C10H18O | |
Molar mass | 154.253 g·mol−1 |
Appearance | Colorless oil |
Density | 0.858 to 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) |
1.589 g/l | |
Hazards | |
NFPA 704 (fire diamond) | |
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).
|
Linalool ( /lɪˈnæloʊɒl, laɪ-, -loʊoʊl, -ˈluːl/) refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. [1] Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness). [2] [3] A colorless oil, linalool is classified as an acyclic monoterpenoid. [1] In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. [1] Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. [1] Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate. [4]
The word linalool is based on linaloe (a type of wood) and the suffix -ol. [5] In food manufacturing, it may be called coriandrol. [1]
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.), cymbopogon ( Cymbopogon martini var. martinii), and sweet orange ( Citrus sinensis) flowers. (R)-linalool is present in lavender ( Lavandula officinalis), bay laurel (Laurus nobilis), and sweet basil (Ocimum basilicum), among others.
Each enantiomer evokes distinct neural responses in humans, so each is 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).
Over 200 species of plants produce linalool, notably 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 was first synthesized in the laboratory of Leopold Ružička in 1919. [11]
In higher plants linalool is formed by rearrangement of geranyl pyrophosphate (GPP). [12] With the aid of linalool synthase (LIS), water attacks to form the chiral center. [13] [12] LIS appears to show a limonene synthase-type catalysis through a simplified "metal-cofactor-binding domain [where the majority] of the residues involved in substrate...binding [are] in the C-terminal part of the protein" suggesting stereoselectivity and the reasoning behind why some plants have varying levels of each enantiomer. [14] [15]
Linalool has complex odor and flavor properties. Its odor is similar to floral, spicy wood, somewhat resembling French lavender plants, bergamot oil or lily of the valley. [1] It has a light, citrus-like flavor, sweet with a spicy tropical accent. [1] Linalool is used as a scent in perfumed hygiene products and cleaning agents, including soaps, detergents, shampoos, and lotions. [1] [2] It exhibits antimicrobial and antifungal properties. [1] [16]
Linalool is hydrogenated to give dihydro- and tetrahydrolinalool, which are fragrances that are more resilient toward oxidants, as might be found in household cleaning products. Linalyl acetate, a popular scent, is produced by esterification of linalool (as well as occurring naturally). Isomerization of linalool gives geraniol and nerol. [17]
Linalool can be absorbed by inhalation of its aerosol and by oral intake or skin absorption, potentially causing irritation, pain and allergic reactions. [2] [18] Some 7% of people undergoing patch testing in Europe were found to be allergic to the oxidized form of linalool. [19]
The US Food and Drug Administration (FDA) lists linalool in the Code of Federal Regulations under substances generally recognized as safe, synthetic flavoring substances and adjuvants. [20]