Each enantiomer evokes distinct neural responses in humans, so each is classified as possessing distinctscents. (S)-(+)-Linalool is perceived as sweet, floral,petitgrain-like (odor threshold 7.4 ppb) and the (R)-form as more woody andlavender-like (odor threshold 0.8 ppb).
Linalool is produced commercially from several terpenes and terpenoid precursors, which are often components ofterpentine. 2-Pinanol, derived frompinene, giveslinalool upon pyrolysis.[13]
Inhigher plants linalool is formed by rearrangement ofgeranyl pyrophosphate (GPP).[14] With the aid oflinalool synthase (LIS), water attacks to form the chiral center.[15][14] LIS appears to show alimonene 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" suggestingstereoselectivity and the reasoning behind why some plants have varying levels of each enantiomer.[16][17]
Linalool has complex odor and flavor properties. Its odor is similar to floral, spicy wood, somewhat resemblingFrench lavender plants,bergamot oil orlily of the valley.[1] It has a light, citrus-like flavor, sweet with a spicy tropical accent.[1] Linalool is used as a scent inperfumed hygiene products and cleaning agents, includingsoaps,detergents,shampoos, and lotions.[1][3] It exhibits antimicrobial and antifungal properties.[1][18]
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 givesgeraniol andnerol.[2]
Linalool can be absorbed by inhalation of itsaerosol and by oral intake or skin absorption, potentially causing irritation, pain andallergic reactions.[3][19] Some 7% of people undergoingpatch testing in Europe were found to be allergic to theoxidized form of linalool.[20]
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.[21]
^Letizia, C.S; Cocchiara, J.; Lalko, J.; Api, A.M (2003). "Fragrance material review on linalool".Food and Chemical Toxicology.41 (7):943–964.doi:10.1016/S0278-6915(03)00015-2.PMID12804650.
^Kasper S, Gastpar M, Müller WE, Volz HP, Möller HJ, Dienel A, Schläfke S (September 2010). "Silexan, an orally administered Lavandula oil preparation, is effective in the treatment of 'subsyndromal' anxiety disorder: a randomized, double-blind, placebo controlled trial".International Clinical Psychopharmacology.25 (5):277–87.doi:10.1097/YIC.0b013e32833b3242.PMID20512042.S2CID46290020.
^Ibrahim EA, Wang M, Radwan MM, Wanas AS, Majumdar CG, Avula B, et al. (March 2019). "Analysis of Terpenes in Cannabis sativa L. Using GC/MS: Method Development, Validation, and Application".Planta Medica.85 (5):431–438.Bibcode:2019PlMed..85..431I.doi:10.1055/a-0828-8387.PMID30646402.S2CID58668648.
^Klimankova E, Holadová K, Hajšlová J, Čajka T, Poustka J, Koudela M (2008). "Aroma profiles of five basil (Ocimum basilicum L.) cultivars grown under conventional and organic conditions".Food Chemistry.107 (1):464–472.doi:10.1016/j.foodchem.2007.07.062.
^Hussain, Abdullah Ijaz; Anwar, Farooq; Hussain Sherazi, Syed Tufail; Przybylski, Roman (2008). "Chemical composition, antioxidant and antimicrobial activities of basil (Ocimum basilicum) essential oils depends on seasonal variations".Food Chemistry.108 (3):986–995.doi:10.1016/j.foodchem.2007.12.010.PMID26065762.
^"Linalool". Toxnet, National Library of Medicine, US National Institutes of Health. 14 January 2016. Archived fromthe original on 28 February 2019. Retrieved21 May 2019.
^Ung CY, White JM, White IR, Banerjee P, McFadden JP (March 2018). "Patch testing with the European baseline series fragrance markers: a 2016 update".The British Journal of Dermatology.178 (3):776–780.doi:10.1111/bjd.15949.PMID28960261.S2CID4434234.
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