Linalool

Linalool
	3,7-dimetilokta-1,6-dien-3-ol
Identifikacija
CAS registarski broj	78-70-6 , 126-91-0 (R) , 126-90-9 (S)
PubChem	6549, ; 443158 (R), ; 67179 (S)
ChemSpider	13849981
UNII	D81QY6I88E
ChEBI	17580
ChEMBL	CHEMBL25306
Jmol-3D slike	Slika 1
SMILES
	CC(O)(C=C)CCC=C(C)C
InChI
	InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3 ; Kod: CDOSHBSSFJOMGT-UHFFFAOYSA-N InChI=1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3; Kod: CDOSHBSSFJOMGT-UHFFFAOYAV
Svojstva
Molekulska formula	C10H18O
Molarna masa	154,25 g/mol
Gustina	0,858 – 0,868 g/cm3
Tačka topljenja	< −20 °C
Tačka ključanja	198–199 °C
Rastvorljivost u vodi	1,589 g/l
Opasnost
NFPA 704	2 1 0
Tačka paljenja	55 °C
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Linalool je prirodni terpenski alkohol koji je prisutan u mnogim cvetajućim i začinskim biljkama. On ima mnoštvo komercijalnih primena, većina kojih se bazira na prijatnom mirisu. Njegova druga imena su: β-linalool, linalil alkohol, linaloil oksid, p-linalool, alo-ocimenol, i 2,6-dimetil-2,7-oktadien-6-ol.

Priroda

Preko 200 biljnih vrsta proizvodi linalool. One su uglavnom iz porodica Lamiaceae (menta, mirišljave trave), Lauraceae (lavor, cimet, palisandrovo drvo), i Rutaceae (citrusno voće).

Enantiomeri

Linalool ima stereogeni centar na C₃ i stoga postoje dva stereoizomera: (R)-(–)-linalool je takođe poznat kao likareol i (S)-(+)-linalool ili koriandrol.

(S)-(+)-linalool (levo) i (R)-(–)-linalool (desno)

Literatura

Casabianca H, Graff JB, Faugier V, Fleig F, Grenier C (1998) Enantiomeric distribution studies of linalool and linalyl acetate. A powerful tool for authenticity control of essential oils. HRC J High Res Chrom 21:107-112
Lewinshon E, Schalechet F, Wilkinson J, Matsui K, Tadmor Y, Nam K, Amar O, Lastochkin E, Larkov O, Ravid U, Hiatt W, Gepstein S, Pichersky E (2001) Enhanced levels of the aroma and flavor compound S-linalool by metabolic engineering of the terpenoid pathway in tomato fruits. Plant Physiol 127:1256–1265
Pengelly, Andrew. The Constituents of Medicinal Plants. 2nd Ed. 2004. CABI Publishing, U.S.A. and UK.
Raguso RA, Pichersky E (1999) A day in the life of a linalool molecule: chemical communication in a plant-pollinator system. Part 1: linalool biosynthesis in flowering plants. Plant Species Biol 14:95-120
Akio Nakamura, Satoshi Fujiwara, Ichiro Matsumoto and Keiko Abe. Stress Repression in Restrained Rats by (R)-(−)-Linalool Inhalation and Gene Expression Profiling of Their Whole Blood Cells. J. Agric. Food Chem., 2009, 57 (12), pp 5480–5485.

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Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

Povezano

Spoljašnje veze

Portal Hemija

Comprehensive data sheet Arhivirano 2013-10-07 na Wayback Machine-u
Record in the Household Products Database of NLM

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

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