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74856 Fluka

(−)-Linalool

analytical standard

Synonym: (R)-(−)-3,7-Dimethyl-1,6-octadien-3-ol

  • CAS Number 126-91-0

  • Linear Formula (CH3)2C=CHCH2CH2C(CH3)(OH)CH=CH2

  • Molecular Weight 154.25

  •  Beilstein Registry Number 1721487

  •  EC Number 204-811-2

  •  MDL number MFCD00135469

  •  PubChem Substance ID 24886737

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Properties

Related Categories Alcohols, Aliphatic, All Alphabetically Sorted, Alphabetical Index of Analytical Standards, Analytical Standards,
grade   analytical standard
assay   ≥98.0% (sum of enantiomers, GC)
optical activity   [α]20/D −20±2°, neat
shelf life   limited shelf life, expiry date on the label
refractive index   n20/D 1.4615(lit.)
  n20/D 1.462
bp   198 °C(lit.)
density   0.862 g/mL at 20 °C(lit.)

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/37
RIDADR 
NA 1993 / PGIII
WGK Germany 
3
RTECS 
RG5800000
Flash Point(F) 
168.8 °F
Flash Point(C) 
76 °C

Protocols & Articles

Related Content

Flavor and Fragrance Analysis

It’s all about your workflow. Sample preparation, separation, detection and analysis. Speed and resolution is key in determining purity or verifying composition.
Keywords: Calorimetry, Gas chromatography, Mass spectrometry, Sample preparations, Separation

Reliable Identification of F&F Components by GC/MS and Linear Retention Indices and Multidimensional Chromatography [VIDEO]

In this on-demand webinar by Prof. Luigi Mondello of the University of Messina, Italy, highlights the shortcomings of GC/MS analysis in the identification of F&F compounds when using a straightforwar...
Keywords: Chromatography, Gas chromatography, High performance liquid chromatography, Mass spectrometry

Peer-Reviewed Papers

References

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A toxicologic and dermatologic assessment of linalool and related esters when used as fragrance ingredients. Bickers D, Calow P, Greim H, et al. Food Chem. Toxicol. 41(7), 919-42, (2003)

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Species-specific effects of herbivory on the oviposition behavior of the moth Manduca sexta. Reisenman CE, Riffell JA, Duffy K, et al. J. Chem. Ecol. 39(1), 76-89, (2013)

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Specific herbivore-induced volatiles defend plants and determine insect community composition in the field. Xiao Y, Wang Q, Erb M, et al. Ecol. Lett. 15(10), 1130-9, (2012)

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Aroma profiles and preferences of Jasminum sambac L. flowers grown in Thailand. Kanlayavattanakul M, Kitsiripaisarn S, and Lourith N J. Cosmet. Sci. 64(6), 483-93, (2013)

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β-Cyclodextrin-complexed (-)-linalool produces antinociceptive effect superior to that of (-)-linalool in experimental pain protocols. Quintans-Júnior LJ, Barreto RS, Menezes PP, et al. Basic Clin Pharmacol Toxicol. 113(3), 167-72, (2013)

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Assessment of the acaricidal activity of carvacrol, (E)-cinnamaldehyde, trans-anethole, and linalool on larvae of Rhipicephalus microplus and Dermacentor nitens (Acari: Ixodidae). de Oliveira Souza Senra T, Zeringóta V, de Oliveira Monteiro CM, et al. Parasitol. Res. 112(4), 1461-6, (2013)

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[Study on the chemical components, antimicrobial and antitumor activities of the essential oil from the leaves of Zanthoxylum avicennae]. Zhang DS, Zhong QX, Song XM, et al. Zhong Yao Cai 35(8), 1263-7, (2012)

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Air-oxidized linalool: a frequent cause of fragrance contact allergy. Bråred Christensson J, Andersen KE, Bruze M, et al. Contact Dermatitis 67(5), 247-59, (2012)

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Toxicology of selected pesticides, drugs, and chemicals. D-limonene, linalool, and crude citrus oil extracts. Hooser SB Vet. Clin. North Am. Small Anim. Pract. 20(2), 383-5, (1990)

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The early bee catches the flower - circadian rhythmicity influences learning performance in honey bees, Apis mellifera Marina Lehmann et al Behav. Ecol. Sociobiol. 65, 205-215, (2010)

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Potential source of S-(+)-linalool from Cinnamomum osmophloeum ct. linalool leaf: essential oil profile and enantiomeric purity. Cheng BH, Lin CY, Yeh TF, et al. J. Agric. Food Chem. 60(31), 7623-8, (2012)

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Functional genomics reveals that a compact terpene synthase gene family can account for terpene volatile production in apple. Nieuwenhuizen NJ, Green SA, Chen X, et al. Plant Physiol. 161(2), 787-804, (2013)

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Fragrance material review on linalool. Letizia CS, Cocchiara J, Lalko J, et al. Food Chem. Toxicol. 41(7), 943-64, (2003)

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Effect of linalool as a component of Humulus lupulus on doxorubicin-induced antitumor activity. Miyashita M and Sadzuka Y Food Chem. Toxicol. 53, 174-9, (2013)

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Antidepressant activity of Litsea glaucescens essential oil: identification of β-pinene and linalool as active principles. Guzmán-Gutiérrez SL, Gómez-Cansino R, García-Zebadúa JC, et al. J. Ethnopharmacol. 143(2), 673-9, (2012)

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Anti-inflammatory effects of linalool in RAW 264.7 macrophages and lipopolysaccharide-induced lung injury model. Huo M, Cui X, Xue J, et al. J. Surg. Res. 180(1), e47-54, (2013)

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Chemical composition, olfactory analysis and antibacterial activity of Thymus vulgaris chemotypes geraniol, 4-thujanol/terpinen-4-ol, thymol and linalool cultivated in southern France. Schmidt E, Wanner J, Hiiferl M, et al. Nat. Prod. Commun. 7(8), 1095-8, (2012)

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An investigation on the chemotactic responses of different entomopathogenic nematode strains to mechanically damaged maize root volatile compounds. Laznik Z and Trdan S Exp. Parasitol. 134(3), 349-55, (2013)

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In vitro neuropeptide Y mRNA expressing model for screening essences that may affect appetite using Rolf B1.T cells. Chen SW, Wu PJ, and Chiang BH J. Agric. Food Chem. 60(32), 7824-9, (2012)

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Isolation and biological activities of decanal, linalool, valencene, and octanal from sweet orange oil. Liu K, Chen Q, Liu Y, et al. J. Food Sci. 77(11), C1156-61, (2012)

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Season's variation impact on Citrus aurantium leaves essential oil: chemical composition and biological activities. Ellouze I, Abderrabba M, Sabaou N, et al. J. Food Sci. 77(9), T173-80, (2012)

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Chemical composition, antioxidant, and antimicrobial activities of essential oil from pine needle (Cedrus deodara). Zeng WC, Zhang Z, Gao H, et al. J. Food Sci. 77(7), C824-9, (2012)

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Volatiles from apple trees infested with light brown apple moth larvae attract the parasitoid Dolichogenidia tasmanica. Suckling DM, Twidle AM, Gibb AR, et al. J. Agric. Food Chem. 60(38), 9562-6, (2012)

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Monitoring of biotransformation of hop aroma compounds in an in vitro digestion model. Heinlein A and Buettner A Food Funct. 3(10), 1059-67, (2012)

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Addendum to Fragrance material review on linalool. Lapczynski A, Letizia CS, and Api AM Food Chem. Toxicol. 46 Suppl 11, S190-2, (2008)

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Fragrance material review on l-linalool. Lapczynski A, Bhatia SP, Letizia CS, et al. Food Chem. Toxicol. 46 Suppl 11, S195-6, (2008)

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Fragrance material review on d-linalool. Lapczynski A, Letizia CS, and Api AM Food Chem. Toxicol. 46 Suppl 11, S193-4, (2008)

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Environmental and seasonal influences on red raspberry flavour volatiles and identification of quantitative trait loci (QTL) and candidate genes. Paterson A, Kassim A, McCallum S, et al. Theor. Appl. Genet. 126(1), 33-48, (2013)

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Influence of yeast mannoproteins in the aroma improvement of white wines. Juega M, Nunez YP, Carrascosa AV, et al. J. Food Sci. 77(8), M499-504, (2012)

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Intraplantar injection of linalool reduces paclitaxel-induced acute pain in mice. Katsuyama S, Kuwahata H, Yagi T, et al. Biomed. Res. 33(3), 175-81, (2012)

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α-Linalool - a marker compound of forged/synthetic sweet basil (Ocimum basilicum L.) essential oils. Radulović NS, Blagojević PD, and Miltojević AB J. Sci. Food Agric. 93(13), 3292-303, (2013)

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Characterization of aroma compounds in Chinese bayberry (Myrica rubra Sieb. et Zucc.) by gas chromatography mass spectrometry (GC-MS) and olfactometry (GC-O). Kang W, Li Y, Xu Y, et al. J. Food Sci. 77(10), C1030-5, (2012)

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Myrtus communis L. infusions: the effect of infusion time on phytochemical composition, antioxidant, and antimicrobial activities. Messaoud C, Laabidi A, and Boussaid M J. Food Sci. 77(9), C941-7, (2012)

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Physical and psychologic effects of aromatherapy inhalation on pregnant women: a randomized controlled trial. Igarashi T J. Altern. Complement. Med. 19(10), 805-10, (2013)

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Relationship between mood change, odour and its physiological effects in humans while inhaling the fragrances of essential oils as well as linalool and its enantiomers. Sugawara Y, Shigetho A, Yoneda M, et al. Molecules 18(3), 3312-38, (2013)

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Cardiovascular effects induced by linalool in normotensive and hypertensive rats. Anjos PJ, Lima AO, Cunha PS, et al. Z. Naturforsch. C 68(5-6), 181-90, (2013)

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Synergistic antiproliferative and anticholesterogenic effects of linalool, 1,8-cineole, and simvastatin on human cell lines. Rodenak Kladniew B, Polo M, Montero Villegas S, et al. Chem. Biol. Interact. 214, 57-68, (2014)

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Beil. 1,IV,2270

Arctander, 1803 / FT-IR 1 (1), 148:C

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