Structure of Linalool
CAS No.: 78-70-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Linalool, a natural product isolated and purified from the leaves of Cinnamomum camphora, has been shown to have antinociceptive, antimicrobial, and anti-inflammatory properties.
Synonyms: dl-Linalool; Phantol; AI3-00942
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Pokajewicz, Katarzyna ; Biernat, Tomasz ; Wieczorek, Piotr P ;
Abstract: Linalyl anthranilate (LNA) has been identified in a number of plant extracts and essential oils by various authors using gas chromatography−mass spectrometry (GC-MS). However, the reported retention behavior of LNA in these studies is inconsistent with the retention data provided in the NIST database. Therefore, the objective of this study was to determine whether the reports of LNA were the result of misidentifications in GC-MS analyses or if the linear NIST retention index was inaccurate. To accomplish this, linalyl anthranilate was synthesized in a two-step procedure, and the resulting product was authenticated using nuclear magnetic resonance (NMR) and GC-MS analyses. This is a new synthetic route to linalyl anthranilate. Subsequently, retention indices for linalyl anthranilate were determined on three commonly used GC phases: polydimethylsiloxane, 5% diphenyl−95% polydimethylsiloxane, and polyethylene glycol. The study confirmed the accuracy of the NIST retention data, establishing the linear retention index data for LNA on a semi-nonpolar GC column as 2051. However, LNA reported in the literature by various authors exhibited a retention index in the elution window of approximately 1000−1400, strongly suggesting that these reports were the result of GC-MS misidentifications. A review of all reported occurrences of LNA in natural samples found no credible evidence of its presence. In many cases, it appears to be a misidentification of linalyl acetate caused by the occurrence of an erroneous spectrum in the older versions of the NIST mass spectra database.
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| CAS No. : | 78-70-6 |
| Formula : | C10H18O |
| M.W : | 154.25 |
| SMILES Code : | CC(C)=CCCC(C)(O)C=C |
| Synonyms : |
dl-Linalool; Phantol; AI3-00942
|
| MDL No. : | MFCD00008906 |
| InChI Key : | CDOSHBSSFJOMGT-UHFFFAOYSA-N |
| Pubchem ID : | 6549 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H227-H303-H315-H317-H319-H402 |
| Precautionary Statements: | P210-P261-P264-P272-P273-P280-P302+P352-P305+P351+P338-P312-P333+P313-P337+P313-P370+P378-P403+P235-P501 |
In Vitro:
|
Cell Line
|
Concentration | Treated Time | Description | References |
| SH-SY5Y cells | 0.54 µg/mL | 24 hours | Linalool reduced IL-6 secretion and decreased α-synuclein mRNA expression. | Antioxidants (Basel). 2024 Jul 29;13(8):917 |
| human dermal microvascular endothelial cells (HDMECs) | 0.25-2 mM | 24 hours | Inhibited HDMEC proliferation, migration, tube formation and spheroid sprouting | Angiogenesis. 2021 Aug;24(3):613-630 |
| Saprolegnia parasitica CQT2 spores | 0.025% (vol/vol, 0.216 mg/ml) | 24 hours | Linalool exhibited strong anti-oomycete activity, inhibiting spore growth. | Elife. 2025 Apr 4;13:RP100393 |
| Saprolegnia parasitica CQT2 mycelium | 0.05% (vol/vol, 0.432 mg/ml) | 60 hours | Linalool disrupted the mycelium cell membrane, causing intracellular component leakage, and inhibited ribosome function to suppress protein synthesis, ultimately affecting mycelium growth. | Elife. 2025 Apr 4;13:RP100393 |
| human embryonic kidney 293 cells (HEK293) | 117 μM (EC50) | To evaluate the activation of TRPA1 and TRPV1 channels by linalool. Results showed that linalool activated TRPA1 channels but not TRPV1 channels. | Br J Pharmacol. 2009 Aug;157(8):1398-409 | |
| dorsal root ganglia neurons | 500 μM | 5 seconds | To evaluate the activation of TRPA1 and TRPV1 channels by linalool. Results showed that linalool activated TRPA1 channels but not TRPV1 channels. | Br J Pharmacol. 2009 Aug;157(8):1398-409 |
| HeyA8 cells | 0.3 mM | 24 h, 48 h, 72 h | To evaluate the cytotoxicity and pro-apoptotic effects of LN-NE-DOX-liposomes. Results showed that LN-NE-DOX-liposomes significantly increased apoptosis in HeyA8 cells (significant increase at 72 h, *p < 0.001) and exhibited higher cytotoxicity than DOX alone or DOX-liposomes (IC50: 0.25 μM vs 1.18 μM and 2.81 μM). | Int J Nanomedicine. 2020 Oct 29;15:8427-8436 |
| HEK293 cells | 6.7 ± 2.0 μM | To test the agonistic effect of Linalool on mTRPM8, results showed that Linalool is a weak TRPM8 agonist. | Br J Pharmacol. 2004 Feb;141(4):737-45 | |
| Caco-2 cells | 0.5 mM | 3 hours | To investigate the bioavailability of linalool, results showed that linalool exhibited moderate permeability in Caco-2 cells. | J Lipid Res. 2014 Jun;55(6):1098-110 |
| HepG2 cells | 1 mM | 24 hours | To study the effect of linalool on intracellular triglyceride concentrations, results showed that linalool significantly reduced intracellular triglyceride accumulation. | J Lipid Res. 2014 Jun;55(6):1098-110 |
| Primary cortical neurons | 0.1, 1, 10 nM | 24 hours | Linalool upregulated protein expression of SirT1, GABA A-α1, and GABA B in MPP+-treated primary cortical neurons. | Int J Mol Sci. 2024 Feb 21;25(5):2514 |
| Primary mesencephalic neurons | 0.1, 1, 10 nM | 24 hours | Linalool enhanced the expressions of TH, SirT1, and parkin in MPP+-treated primary mesencephalic neurons. | Int J Mol Sci. 2024 Feb 21;25(5):2514 |
| SH-SY5Y cells | 1 pM–1 µM | 24 hours | Linalool increased cell viability in MPP+-treated SH-SY5Y cells, reduced neurite retraction, enhanced antioxidant defense by downregulating apoptosis signaling (Bcl-2, cleaved caspase-3, and PARP) and phagocyte NADPH oxidase (gp91phox), and upregulated neurotrophic signaling (BDNF and NGF) and the Nrf2/HO-1 pathway. | Int J Mol Sci. 2024 Feb 21;25(5):2514 |
In Vivo:
|
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
| BALB/c mice | Matrigel plug model | Subcutaneous injection | 2 mM | Single dose, lasted for 7 days | Evaluated the effect of Linalool on in vivo angiogenesis, showing a significant reduction in microvessel density | Angiogenesis. 2021 Aug;24(3):613-630 |
| Grass carp (Ctenopharyngodon idella) | Saprolegnia parasitica infection model | Immersion | 0.00039% | Daily immersion for 7 days | Linalool enhanced the complement and coagulation system to activate host immune defense and lyse S. parasitica cells, promoted wound healing and tissue repair, modulated gut microbiota to increase beneficial Actinobacteriota abundance, and stimulated inflammatory cytokine and chemokine production. | Elife. 2025 Apr 4;13:RP100393 |
| BALB/c nude mice | HeyA8 EOC tumor model | Intravenous injection | 100 mg/kg | LN: twice a week, DOX: once a week, for 3-4 weeks | To evaluate the antitumor efficacy and biochemical toxicity of LN-NE-DOX-liposomes. Results showed that LN-NE-DOX-liposomes significantly inhibited HeyA8 EOC tumor growth (75% reduction, ***p < 0.001), reduced the number of tumor nodules (***p < 0.01), and did not cause significant biochemical toxicity (AST, ALT, BUN levels were not significantly different from the control group). | Int J Nanomedicine. 2020 Oct 29;15:8427-8436 |
| C57BL/6J mice | Western-diet-induced hypertriglyceridemia model | Oral | 100 mg/kg body weight/day | Once daily for 3 weeks | To investigate the effect of linalool on plasma triglyceride concentrations, results showed that linalool significantly reduced plasma triglyceride levels. | J Lipid Res. 2014 Jun;55(6):1098-110 |
| C57BL/6 mice | MPTP-induced Parkinson's disease model | Oral | 12.5 and 25 mg/kg | Once daily for 7 days | Linalool attenuated the loss of dopamine neurons in SNpc and improved motor and nonmotor behavioral deficits and muscle strength in MPTP-induced PD-like mice. | Int J Mol Sci. 2024 Feb 21;25(5):2514 |
| Mice | Anxiety-like behavior model | Inhalation | 0.08% | 2 hours per day for 7 consecutive days | Linalool reduces anxiety-like behaviors and increases dentate granule cell activity in mice by activating hippocampal endocannabinoid signaling. | Int J Mol Sci. 2024 Oct 4;25(19):10699 |
Clinical Trial:
| NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
| NCT03369132 | Sore Throat | Not Applicable | Recruiting | September 30, 2018 | Czechia ... More >> MUDr. Lenka Dybova Recruiting Brno, Czechia, 602 00 Contact: Lenka Dybova, M. D. MUDr. Libor Hemzsky Recruiting Choltice, Czechia, 533 61 Contact: Libor Hemzsky, M. D. NEFROMED s.r.o. Recruiting Dejvice, Czechia, 160 00 Contact: Krisitina Sadilkova, M. D. MEDIGATE care s.r.o Recruiting Hradec Králové, Czechia, 500 09 Contact: Ivana Skardova, M. D. Sub-Investigator: Jan Skarda, M. D. MUDr. Petra Hoskova Recruiting Hradec Králové, Czechia, 500 09 Contact: Petra Hoskova, M. D. MUDr. Jana Dvorakova s.r.o. Recruiting Hradec Králové, Czechia, 500 11 Contact: Jana Dvorakova, M. D. MUDr. Danuse Mikeschova Recruiting Karlovy Vary, Czechia, 360 17 Contact: David Macharacek, M. D. Azita s.r.o. Recruiting Malšice, Czechia, 108 00 Contact: Azita Gebauerova, M. D. Fortmedica s.r.o. Recruiting Praha 4, Czechia, 143 00 Contact: Tomas Fort, M. D. Sub-Investigator: Daniel Groh, M. D. GM ordinace s.r.o Recruiting Praha 4, Czechia, 148 00 Contact: David Macharacek, M. D. MUDr Sylva Kohoutova Recruiting Praha 6, Czechia, 160 00 Contact: Sylva Kohoutova, M. D. Ordinace Optima s.r.o Recruiting Praha 6, Czechia, 161 00 Contact: Radka Majerova, M. D. MUDr. Lenka Fejfarova Recruiting Praha 6, Czechia, 164 00 Contact: Lenka Fejfarova, M. D. Saniga s.r.o. Recruiting Sokolov, Czechia, 356 01 Contact: Zdenek Vlasak, M. D. MUDr. Jan Bartusek Recruiting Teplice, Czechia, 415 01 Contact: Jan Bartusek, M. D. A-MEDICOS s.r.o. Recruiting Zlín, Czechia, 760 01 Contact: Alena Malikova, M. D. Less << |
| NCT03445130 | Anxiety | Not Applicable | Not yet recruiting | March 2020 | - |
Tags: Linalool | iGluR | Apoptosis | Endogenous Metabolite | Ionotropic glutamate receptors | 78-70-6 |
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