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Chemical Compound Review

L-Linalool     (3R)-3,7-dimethylocta-1,6- dien-3-ol

Synonyms: CHEBI:28, CPD-8997, AG-D-56329, BSPBio_002785, KBioGR_002294, ...
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Disease relevance of C11389


Psychiatry related information on C11389

  • A blend of active cuticular compounds with linalool elicited both attraction and copulation behavior in patrolling males [6].

High impact information on C11389

  • Green fluorescent protein localization experiments suggest that a change in subcellular localization led to the FaNES1 enzyme encountering both GPP and FPP, allowing it to produce linalool and nerolidol [7].
  • The utility of these cyclization reactions was illustrated with the synthesis of a key tetrahydrofuran building block for the synthesis of linalool oxide and rotundisine [8].
  • The partial pressure rises also in compounds with a low H, but more than 1,000-fold higher liquid phase concentrations of linalool and 1,8-cineole are necessary to increase intercellular partial pressure high enough to balance stomatal closure [9].
  • The local lymph node assay (LLNA) was used to investigate the sensitizing potential of pure linalool, two samples of air-exposed linalool, and oxidation products of linalool (an alpha,beta-unsaturated aldehyde, a mixture of two hydroperoxides, and an alcohol) [10].
  • Cytochrome P-450lin catalyzes the 8-methyl hydroxylation of linalool as the first committed step of its utilization by Pseudomonas incognita as the sole carbon source [11].

Chemical compound and disease context of C11389


Biological context of C11389

  • In the case of linalool, the lag times for PL with 5 and 10% levels of enhancer were 7.0- and 5.2-fold less compared with 1% level [16].
  • (E)-Nerolidol, a minor component of the hydrodistillate, as well as linalool, were shown to have a more potent and selective effect on the trypanosomes [IC50 = 1.7 and 2.5 microg/mL (7.6 and 16.3 microM) with SI = 35.7 and > 40, respectively] [17].
  • In addition, OTFP also reduced the amplitude of the EAG response to linalool, a monoterpenic alcohol, but not its kinetics [18].
  • Thus, it was concluded that scent of lavender oil and its active component, linalool, affects autonomic neurotransmission and reduces blood pressure through the central histaminergic nervous system and the SCN [3].
  • Biotransformation of (R)-(-)-linalool with the same strain yielded almost pure trans-furanoid and trans-pyranoid linalool oxide (ee > 95) [19].

Anatomical context of C11389


Associations of C11389 with other chemical compounds


Gene context of C11389


Analytical, diagnostic and therapeutic context of C11389


  1. Protein components of a cytochrome P-450 linalool 8-methyl hydroxylase. Ullah, A.J., Murray, R.I., Bhattacharyya, P.K., Wagner, G.C., Gunsalus, I.C. J. Biol. Chem. (1990) [Pubmed]
  2. Olfactory stimulation with scent of lavender oil affects autonomic nerves, lipolysis and appetite in rats. Shen, J., Niijima, A., Tanida, M., Horii, Y., Maeda, K., Nagai, K. Neurosci. Lett. (2005) [Pubmed]
  3. Olfactory stimulation with scent of lavender oil affects autonomic neurotransmission and blood pressure in rats. Tanida, M., Niijima, A., Shen, J., Nakamura, T., Nagai, K. Neurosci. Lett. (2006) [Pubmed]
  4. Thauera linaloolentis sp. nov. and Thauera terpenica sp. nov., isolated on oxygen-containing monoterpenes (linalool, menthol, and eucalyptol) nitrate. Foss, S., Harder, J. Syst. Appl. Microbiol. (1998) [Pubmed]
  5. Toxic effects of lemon peel constituents on Ceratitis capitata. Salvatore, A., Borkosky, S., Willink, E., Bardón, A. J. Chem. Ecol. (2004) [Pubmed]
  6. Cuticular hydrocarbons as sex pheromone of the bee Colletes cunicularius and the key to its mimicry by the sexually deceptive orchid, Ophrys exaltata. Mant, J., Brändli, C., Vereecken, N.J., Schulz, C.M., Francke, W., Schiestl, F.P. J. Chem. Ecol. (2005) [Pubmed]
  7. Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species. Aharoni, A., Giri, A.P., Verstappen, F.W., Bertea, C.M., Sevenier, R., Sun, Z., Jongsma, M.A., Schwab, W., Bouwmeester, H.J. Plant Cell (2004) [Pubmed]
  8. Oxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic Acid. Liu, B., Duan, S., Sutterer, A.C., Moeller, K.D. J. Am. Chem. Soc. (2002) [Pubmed]
  9. Stomatal constraints may affect emission of oxygenated monoterpenoids from the foliage of Pinus pinea. Niinemets, U., Reichstein, M., Staudt, M., Seufert, G., Tenhunen, J.D. Plant Physiol. (2002) [Pubmed]
  10. Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization. Sköld, M., Börje, A., Harambasic, E., Karlberg, A.T. Chem. Res. Toxicol. (2004) [Pubmed]
  11. Cloning and expression of a member of a new cytochrome P-450 family: cytochrome P-450lin (CYP111) from Pseudomonas incognita. Ropp, J.D., Gunsalus, I.C., Sligar, S.G. J. Bacteriol. (1993) [Pubmed]
  12. Hepatic peroxisomal and microsomal enzyme induction by citral and linalool in rats. Roffey, S.J., Walker, R., Gibson, G.G. Food Chem. Toxicol. (1990) [Pubmed]
  13. Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae). Jang, Y.S., Yang, Y.C., Choi, D.S., Ahn, Y.J. J. Agric. Food Chem. (2005) [Pubmed]
  14. Skin diseases in workers at a perfume factory. Schubert, H.J. Contact Derm. (2006) [Pubmed]
  15. Facial psoriasis caused by contact allergy to linalool and hydroxycitronellal in an after-shave. de Groot, A.C., Liem, D.H. Contact Derm. (1983) [Pubmed]
  16. Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin. Kunta, J.R., Goskonda, V.R., Brotherton, H.O., Khan, M.A., Reddy, I.K. Journal of pharmaceutical sciences. (1997) [Pubmed]
  17. Antitrypanosomal compounds from the leaf essential oil of Strychnos spinosa. Hoet, S., Stévigny, C., Hérent, M.F., Quetin-Leclercq, J. Planta Med. (2006) [Pubmed]
  18. Effects of trifluoromethyl ketones and related compounds on the EAG and behavioural responses to pheromones in male moths. Renou, M., Lucas, P., Malo, E., Quero, C., Guerrero, A. Chem. Senses (1997) [Pubmed]
  19. Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger. Demyttenaere, J.C., Willemen, H.M. Phytochemistry (1998) [Pubmed]
  20. Discrimination between Enantiomers of Linalool by Olfactory Receptor Neurons in the Cabbage Moth Mamestra brassicae (L.). Ulland, S., Ian, E., Borg-Karlson, A.K., Mustaparta, H. Chem. Senses (2006) [Pubmed]
  21. Age-related decline of intranasal trigeminal sensitivity: is it a peripheral event? Frasnelli, J., Hummel, T. Brain Res. (2003) [Pubmed]
  22. Linalool suppresses voltage-gated currents in sensory neurons and cerebellar Purkinje cells. Narusuye, K., Kawai, F., Matsuzaki, K., Miyachi, E. Journal of neural transmission (Vienna, Austria : 1996) (2005) [Pubmed]
  23. Effects of Linalool on glutamatergic system in the rat cerebral cortex. Elisabetsky, E., Marschner, J., Souza, D.O. Neurochem. Res. (1995) [Pubmed]
  24. Chromatographic study of terpene derivatives on porous graphitic carbon stationary phase with beta-cyclodextrin as mobile phase modifier. Clarot, I., Clédat, D., Battu, S., Cardot, P.J. Journal of chromatography. A. (2000) [Pubmed]
  25. Racemate and enantiomers of ketoprofen: phase diagram, thermodynamic studies, skin permeability, and use of chiral permeation enhancers. Kommuru, T.R., Khan, M.A., Reddy, I.K. Journal of pharmaceutical sciences. (1998) [Pubmed]
  26. Associative learning of plant odorants activating the same or different receptor neurones in the moth Heliothis virescens. Skiri, H.T., Stranden, M., Sandoz, J.C., Menzel, R., Mustaparta, H. J. Exp. Biol. (2005) [Pubmed]
  27. Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, Fourier transform infrared spectroscopy, and differential scanning calorimetry. Vaddi, H.K., Ho, P.C., Chan, S.Y. Journal of pharmaceutical sciences. (2002) [Pubmed]
  28. Ovicidal and adulticidal activities of Cinnamomum zeylanicum bark essential oil compounds and related compounds against Pediculus humanus capitis (Anoplura: Pediculicidae). Yang, Y.C., Lee, H.S., Lee, S.H., Clark, J.M., Ahn, Y.J. Int. J. Parasitol. (2005) [Pubmed]
  29. Comparison of cultivars of ornamental crop Gerbera jamesonii on production of spider mite-induced volatiles, and their attractiveness to the predator Phytoseiulus persimilis. Krips, O.E., Willems, P.E., Gols, R., Posthumus, M.A., Gort, G., Dicke, M. J. Chem. Ecol. (2001) [Pubmed]
  30. Effects of intraperitoneally administered lipoic acid, vitamin E, and linalool on the level of total lipid and fatty acids in guinea pig brain with oxidative stress induced by H2O2. Celik, S., Ozkaya, A. J. Biochem. Mol. Biol. (2002) [Pubmed]
  31. Effects of linalool on [(3)H]MK801 and [(3)H] muscimol binding in mouse cortical membranes. Brum, L.F., Elisabetsky, E., Souza, D. Phytotherapy research : PTR. (2001) [Pubmed]
  32. Molecular cloning and characterization of a new linalool synthase. Crowell, A.L., Williams, D.C., Davis, E.M., Wildung, M.R., Croteau, R. Arch. Biochem. Biophys. (2002) [Pubmed]
  33. Terpenes in ethanol: haloperidol permeation and partition through human skin and stratum corneum changes. Vaddi, H.K., Ho, P.C., Chan, Y.W., Chan, S.Y. Journal of controlled release : official journal of the Controlled Release Society. (2002) [Pubmed]
  34. Metabolism of geraniol and linalool in the rat and effects on liver and lung microsomal enzymes. Chadha, A., Madyastha, K.M. Xenobiotica (1984) [Pubmed]
  35. Antimicrobial activity of Croton cajucara Benth linalool-rich essential oil on artificial biofilms and planktonic microorganisms. Alviano, W.S., Mendonça-Filho, R.R., Alviano, D.S., Bizzo, H.R., Souto-Padrón, T., Rodrigues, M.L., Bolognese, A.M., Alviano, C.S., Souza, M.M. Oral Microbiol. Immunol. (2005) [Pubmed]
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