Linalool

Linalool
Skeletal formula
Ball-and-stick model
Names
IUPAC name
3,7-dimethylocta-1,6-dien-3-ol
Identifiers
78-70-6 YesY
126-91-0 (R) N
126-90-9 (S) N
3D model (Jmol) Interactive image
ChEBI CHEBI:17580 YesY
ChEMBL ChEMBL25306 YesY
ChemSpider 13849981 YesY
ECHA InfoCard 100.001.032
2469
PubChem 6549
443158 (R)
67179 (S)
UNII D81QY6I88E YesY
Properties
C10H18O
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)
1.589 g/l
Hazards
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
2
1
0
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).
N verify (what is YesYN ?)
Infobox references

Linalool (/lᵻˈnæloʊˌɒl, liː-, -loʊˌɔːl, -ləˌwɒl, -ləˌwoʊl/ or /ˌlɪnəˈluːl/[1][2]) 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.

Nature

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.[3]

Enantiomers

Linalool has a stereogenic center at C3 and therefore there are two stereoisomers: (R)-(–)-linalool is also known as licareol and (S)-(+)-linalool is also known as coriandrol.

(S)-(+)-linalool (left) and (R)-(–)-linalool (right)

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).

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

Linalool is used as a scent in 60–80% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions.[4]

It is also used as a chemical intermediate. One common downstream product of linalool is vitamin E.

In addition, linalool is used by pest professionals as a flea, fruit fly and cockroach insecticide.

Linalool is used in some mosquito-repellent products;[5] 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."[6]

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,[7] 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.[8]

Safety

Patch test

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.[4]

References

  1. ↑ "Linalool". Dictionary.com Unabridged. Random House. Retrieved 2016-01-22.
  2. ↑ "Linalool". Merriam-Webster Dictionary. Retrieved 2016-01-22.
  3. ↑ "Strain Family Gallery: Jack Herer Hybrids". High Times. Retrieved 29 July 2015.
  4. 1 2 "Widely Used Fragrance Ingredients In Shampoos And Conditioners Are Frequent Causes Of Eczema |date March 28, 2009".
  5. ↑ "What to look for when you're buying mosquito repellent". South China Morning Post. September 6, 2015. Retrieved December 30, 2015.
  6. ↑ EPA Linalool Summary Document Registration Review: Initial Docket (PDF) April 2007
  7. ↑ Nakamura, Akio; Fujiwara, S; Matsumoto, I; Abe, K; et al. (20 May 2009). "Stress Repression in Restrained Rats by (R)-(−)-Linalool Inhalation and Gene Expression Profiling of Their Whole Blood Cells". Journal of Agricultural and Food Chemistry. American Chemical Society. 57 (12): 5480–5485. doi:10.1021/jf900420g. PMID 19456160. Retrieved 22 January 2010.
  8. ↑ "Stop and Smell the Flowers – The Scent Can Really Soothe Stress". July 22, 2009.</ref>

    Plants that contain linalool

    • Lavandula<ref>{{cite journal | last = Kasper | first = S. | title = Silexan, an orally administered Lavandula oil preparation, is effective in the treament of 'sybsyndromal' anxiety disorder: a randomized, double-blind, placebo controlled trail | journal = International clinical psychopharmacology | volume = 25 | issue = 5 | pages = 277-87 | year = 2010 | doi = 10.1097/YIC.0b013e32833b3242 | last2 = Gastpar | first2 = M. | last3 = Muller | first3 = W. E. | last4 = Volz | first4 = H. P. | last5 = Moller | first5 = H. J. | last6 = Dienel | first6 = A. Hüsnü|display-authors=etal}}</ref>
    • Cinnamomum tamala<ref name=eocs>{{cite journal | last = Ahmed | first = Aftab | title = Essential oil constituents of the spice ''Cinnamomum tamala'' (Ham.) Nees & Eberm. | journal = Flavour and Fragrance Journal | volume = 15 | issue = 6 | pages = 388–390 | year = 2000 | doi = 10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F | last2 = Choudhary | first2 = M. Iqbal | last3 = Farooq | first3 = Afgan | last4 = Demirci | first4 = Betül | last5 = Demirci | first5 = Fatih | last6 = Can Başer | first6 = K. Hüsnü|display-authors=etal}}</ref>
    • Cannabis sativa
    • Cannabis indica
    • Ocimum basilicum<ref name=apfb>{{cite journal | last = Klimánková | first = Eva | title = Aroma profiles of five basil (Ocimum basilicum L.) cultivars grown under conventional and organic conditions | journal = Food Chemistry | volume = 107 | issue = 1 | pages = 464–472 | year = 2008 | doi = 10.1016/j.foodchem.2007.07.062 | last2 = Holadová | first2 = Kateřina | last3 = Hajšlová | first3 = Jana | last4 = Čajka | first4 = Tomáš | last5 = Poustka | first5 = Jan | last6 = Koudela | first6 = Martin|display-authors=etal}}</ref>
    • Solidago Meyen, Solidago chilensis<ref>Vila, R.; Mundina, M.; Tomi, F. L.; Furlán, R.; Zacchino, S.; Casanova, J.; Cañigueral, S. (2002). "Composition and Antifungal Activity of the Essential Oil of Solidago chilensis". Planta Medica. 68 (2): 164–167. doi:10.1055/s-2002-20253. PMID 11859470.

Further reading

See also

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