Linalool

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Linalool
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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
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3D model (JSmol)
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  • InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3 checkY
    Key: CDOSHBSSFJOMGT-UHFFFAOYSA-N checkY
  • InChI=1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
    Key: CDOSHBSSFJOMGT-UHFFFAOYAV
  • CC(O)(C=C)CCC=C(C)C
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
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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).

Template:Chembox Footer/trackingTemplate:Short description

Linalool (/lɪˈnæloʊɒl, laɪ-, -loʊoʊl, -ˈluːl/), also called linalol[1][2] refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants.[3] Together with geraniol, nerol, and citronellol, linalool is one of the rose alcohols.[4] Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness).[5][6]

A colorless oil, linalool is classified as an acyclic monoterpenoid.[3] In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound.[3] Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides.[3] Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate.[7]

The word linalool is based on linaloe (a type of wood) and the suffix -ol.[8] In food manufacturing, it may be called coriandrol.[3]

Occurrence

File:Linalool Enantiomers Structural Formulae.png
(S)-(+)-linalool (left) and (R)-(–)-linalool (right)

Both enantiomeric forms are found in nature: (S)-linalool (dextro-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 (laevo-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.[14]

Production

Linalool is produced commercially from several terpenes and terpenoid precursors, which are often components of terpentine. 2-Pinanol, derived from pinene, gives linalool upon pyrolysis.[15]

Biosynthesis

In higher plants linalool is formed by rearrangement of geranyl pyrophosphate (GPP).[16] With the aid of linalool synthase (LIS), water attacks to form the chiral center.[17][16] 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.[18][19]

File:Linalool Biosynthesis.png
Linalool biosynthesis pathway. Abbreviations used: geranyl diphosphate synthase (GDS), pyrophosphate ester (OPP), isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl pyrophosphate (GPP). Stereogenic centers are indicated by an asterisk.

Odor and flavor

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.[3] It has a light, citrus-like flavor, sweet with a spicy tropical accent.[3] The aroma of the racemic mixture is described as citrus, floral, sweet, bois de rose, woody, green, blueberry, orange, terpenic, waxy, and rose.[20] The aroma of the laevo enantiomer is described as fresh, floral, woody, natural, and lavender,[21] whilst the dextro enantiomer is described as sweet, floral, petitgrain, and lavender. [22]

Linalool is used as a scent in perfumed hygiene products and cleaning agents, including soaps, detergents, shampoos, and lotions.[3][5] It exhibits antimicrobial and antifungal properties.[3][23]

Chemical derivatives

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.[4]

Safety

Linalool can be absorbed by inhalation of its aerosol and by oral intake or skin absorption, potentially causing irritation, pain and allergic reactions.[5][24] Some 7% of people undergoing patch testing in Europe were found to be allergic to the oxidized form of linalool.[25]

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.[26]

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Linalool". Collins English Dictionary. Retrieved 2026-03-04.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Linalool Definition & Meaning". Dictionary.com. Retrieved 2026-03-04.
  3. ^ a b c d e f g h i Page Module:Citation/CS1/styles.css has no content."Linalool". PubChem, US National Library of Medicine. 16 October 2021. Retrieved 17 October 2021.
  4. ^ a b Page Module:Citation/CS1/styles.css has no content.Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  5. ^ a b c Script error: No such module "Template wrapper".
  6. ^ Page Module:Citation/CS1/styles.css has no content.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.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Croteau, R.; Satterwhite, D. M.; Cane, D. E.; Chang, C. C. (1988). "Biosynthesis of Monoterpenes. Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene". The Journal of Biological Chemistry. 263 (21): 10063–71. doi:10.1016/S0021-9258(19)81477-1. PMID 3392006.
  8. ^ Page Module:Citation/CS1/styles.css has no content."Linalool". Merriam-Webster.com Dictionary. Merriam-Webster. OCLC 1032680871.: "International Scientific Vocabulary, from Mexican Spanish lináloe"
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.
  11. ^ Page Module:Citation/CS1/styles.css has no content.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. PMID 30646402. S2CID 58668648.
  12. ^ Page Module:Citation/CS1/styles.css has no content.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.
  13. ^ Page Module:Citation/CS1/styles.css has no content.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. Bibcode:2002PlMed..68..164V. doi:10.1055/s-2002-20253. PMID 11859470. S2CID 260283973.
  14. ^ Albert Eschenmoser: "Leopold Ruzicka - From the Isoprene Rule to the Question of Life's Origin" CHIMIA 44 (1990)
  15. ^ Script error: No such module "Template wrapper".
  16. ^ a b Page Module:Citation/CS1/styles.css has no content.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. Bibcode:2011PlMed..77....7W. doi:10.1055/s-0030-1250136. PMID 20665367.
  17. ^ Page Module:Citation/CS1/styles.css has no content.Dewick PM (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). John Wiley & Sons. ISBN 978-0-470-74168-9.
  18. ^ Page Module:Citation/CS1/styles.css has no content.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.
  19. ^ Page Module:Citation/CS1/styles.css has no content.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.
  20. ^ Page Module:Citation/CS1/styles.css has no content."Linalool". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  21. ^ Page Module:Citation/CS1/styles.css has no content."laevo-linalool". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  22. ^ Page Module:Citation/CS1/styles.css has no content."dextro-linalool". Scents and Flavors. Scents and Flavors. Retrieved 26 March 2026.
  23. ^ Page Module:Citation/CS1/styles.css has no content.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.
  24. ^ Page Module:Citation/CS1/styles.css has no content."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.
  25. ^ Page Module:Citation/CS1/styles.css has no content.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.
  26. ^ Page Module:Citation/CS1/styles.css has no content."eCFR :: 21 CFR 182.60 -- Synthetic flavoring substances and adjuvants". eCFR. 2021-10-27. Retrieved 2021-10-29.

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