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).
Inhigher 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 oilorlily 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]
^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. 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.
^Vila R, Mundina M, Tomi F, Furlán R, Zacchino S, Casanova J, Cañigueral S (February 2002). "Composition and antifungal activity of the essential oil of Solidago chilensis". Planta Medica. 68 (2): 164–7. doi:10.1055/s-2002-20253. PMID11859470. S2CID260283973.
^Albert Eschenmoser: "Leopold Ruzicka - From the Isoprene Rule to the Question of Life's Origin" CHIMIA 44 (1990)
^"Linalool". Toxnet, National Library of Medicine, US National Institutes of Health. 14 January 2016. Archived from the original on 28 February 2019. Retrieved 21 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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