Linalool

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Linalool
Skeletal formula
Ball-and-stick model
IUPAC ime
Identifikacija
CAS registarski broj 78-70-6 YesY, 126-91-0 (R) YesY, 126-90-9 (S) YesY
PubChem[1][2] 6549
443158 (R), 
67179 (S)
ChemSpider[3] 13849981 YesY
UNII D81QY6I88E YesY
ChEBI 17580
ChEMBL[4] CHEMBL25306 YesY
Jmol-3D slike Slika 1
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
NFPA 704.svg
2
1
0
 
Tačka paljenja 55 °C

 YesY (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[уреди]

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[уреди]

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[уреди]

  • 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[уреди]

  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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