Linalool

Linalool
Nazivi
	IUPAC naziv 3,7-dimetilokta-1,6-dien-3-ol
Identifikacija
CAS broj	78-70-6 ; 126-91-0 (R) ; 126-90-9 (S) ;
3D model (Jmol)	interaktivna slika;
ChEBI	CHEBI:17580 ;
ChemSpider	13849981 ;
ECHA InfoCard	100.001.032
PubChem C ID	6549; 443158 (R); 67179 (S);
UNII	D81QY6I88E ;
	SMILES CC(O)(C=C)CCC=C(C)C; ; ; ; ; ;
Svojstva
Hemijska 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
Opasnosti
NFPA 704	2 1 0
Tačka paljenja	55 °C
	Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje materijala (na 25 °C [77 °F], 100 kPa).
	verifikuj (šta je ?)
	Reference infokutije

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.

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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ 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.

Vidi još

Spoljašnje veze

Comprehensive data sheet
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. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[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.

[1]

[2]