Słodki oral

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Słodki oral
From Wikipedia, the free encyclopedia
Chemical compound with a floral aroma
3,7-Dimethyl-1,6-octadien-3-ol, β-linalool, linalyl alcohol, linaloyl oxide, allo-ocimenol
Compounds (±)-linalool ( R ) : (−)-linalool ( S ) : (+)-linalool
78-70-6 Y ( R ): 126-91-0 Y ( S ): 126-90-9 Y
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3 Y
Key: CDOSHBSSFJOMGT-UHFFFAOYSA-N Y
InChI=1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

^ Jump up to: a b c d e f g h i "Linalool" . PubChem, US National Library of Medicine. 16 October 2021 . Retrieved 17 October 2021 .

^ Jump up to: a b c Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi : 10.1002/14356007.a26_205 .

^ 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 . PMID 12804650 .

^ "Linalool" . Merriam-Webster Dictionary . : "International Scientific Vocabulary, from Mexican Spanish lináloe"

^ 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 . PMID 20512042 . S2CID 46290020 .

^ Ahmed A, Choudhary MI, Farooq A, Demirci B, Demirci F, Can Başer KH (2000). "Essential oil constituents of the spice Cinnamomum tamala (Ham.) Nees & Eberm". Flavour and Fragrance Journal . 15 (6): 388–390. doi : 10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F .

^ 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 . PMID 30646402 . S2CID 58668648 .

^ 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 . PMID 11859470 .

^ Albert Eschenmoser: "Leopold Ruzicka - From the Isoprene Rule to the Question of Life's Origin" CHIMIA 44 (1990)

^ Jump up to: a b Woronuk G, Demissie Z, Rheault M, Mahmoud S (January 2011). "Biosynthesis and therapeutic properties of Lavandula essential oil constituents" . Planta Medica . 77 (1): 7–15. doi : 10.1055/s-0030-1250136 . PMID 20665367 .

^ Dewick PM (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). John Wiley & Sons. ISBN 978-0-470-74168-9 .

^ Cseke L, Dudareva N, Pichersky E (November 1998). "Structure and evolution of linalool synthase" . Molecular Biology and Evolution . 15 (11): 1491–8. doi : 10.1093/oxfordjournals.molbev.a025876 . PMID 12572612 .

^ Iijima Y, Davidovich-Rikanati R, Fridman E, Gang DR, Bar E, Lewinsohn E, Pichersky E (November 2004). "The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil" . Plant Physiology . 136 (3): 3724–36. doi : 10.1104/pp.104.051318 . PMC 527170 . PMID 15516500 .

^ 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 . PMID 26065762 .

^ Yang Z, Bengtsson M, Witzgall P (March 2004). "Host plant volatiles synergize response to sex pheromone in codling moth, Cydia pomonella". Journal of Chemical Ecology . 30 (3): 619–29. doi : 10.1023/b:joec.0000018633.94002.af . PMID 15139312 . S2CID 23472335 .

^ "What to look for when you're buying mosquito repellent" . South China Morning Post . September 6, 2015 . Retrieved December 30, 2015 .

^ "EPA Linalool Summary Document Registration Review: Initial Docket" (PDF) . U.S. Environmental Protection Agency. April 2007.

^ "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 . PMID 28960261 . S2CID 4434234 .

^ "eCFR :: 21 CFR 182.60 -- Synthetic flavoring substances and adjuvants" . eCFR . 2021-10-27 . Retrieved 2021-10-29 .


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Linalool ( / l ɪ ˈ n æ l oʊ ɒ l , l aɪ -, - l oʊ oʊ l , - ˈ l uː l / ) 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]

The word linalool is based on linaloe (a type of wood) and the suffix -ol . [4] 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 different neural responses in humans, so 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 ).

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 was first synthesized in the laboratory of Leopold Ružička in 1919. [10]

The biosynthesis of linalool in higher plants starts at the condensation of dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) to form geranyl pyrophosphate (GPP). [11] With the aid of linalool synthase (LIS), water attacks to form the chiral center. [12] [11] 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. [13] [14]

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 60% to 80% of perfumed hygiene products and cleaning agents, including soaps , detergents , shampoos , and lotions. [1] [2] It exhibits antimicrobial and antifungal properties. [1] [15]

In addition, linalool is used as an insecticide against flea , fruit fly , and cockroach . It can also be used as a method of pest control for codling moths . Linalool creates a synergistic effect with the codling moth's pheromone called codlemone, which increases attraction of males. [16] Linalool is used in some mosquito -repellent products; [17] however, the U.S. 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." [18]

Linalool can be absorbed by inhalation of its aerosol and by oral intake or skin absorption, potentially causing irritation, pain and allergic reactions. [2] [19] Some 7% of people undergoing patch testing in Europe were found to be allergic to the oxidized 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]

198 to 199 °C (388 to 390 °F; 471 to 472 K)


Masovian State University in Plock · Faculty of Health Science
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