Fenkoni Sisällysluettelo Ominaisuudet ja esiintyminen luonnossa | Valmistus ja käyttö | Lähteet | Aiheesta muualla | NavigointivalikkoInfobox OKVirheellinen NIMI-arvoFenchone – Substance summaryTeoksen verkkoversioRoyal Society of Chemistry, ChemSpider : FenchoneDr. Duke's Phytochemical and Ethnobotanical Databases: FenchonePherobase: Floral Compound - fenchonePherobase: Semiochemical - fenchone

KetonitTerpeenit


terpeeneihinorgaaninen yhdistehajusteissakamferinisomeerituoksuissasemiokemikaalinaetanoliindietyylieetteriinoptisesti aktiivinenominaiskiertokykyeteerisissä öljyissäfenkolissatupsulaventelissaenantiomeeriakanadantuijassapineenistäkarboksyylihappojenhydrolysoidaanfenkyylialkoholiksi



























Fenkoni
Fenchon Enantiomers Structural Formulae.png
Tunnisteet
CAS-numero
1195-79-5
IUPAC-nimi
2,2,4-trimetyylibisyklo[2.2.1]heptan-3-oni
SMILES
CC1(C2CCC(C2)(C1=O)C)C[1]
Ominaisuudet
Kemiallinen kaava
C10H16O
Moolimassa
152,228 g/mol
Tiheys
0,947[2] g/cm³
Sulamispiste
6 °C[2]
Kiehumispiste
193,5 °C[2]
Liukoisuus
Ei liukene veteen

Infobox OKVirheellinen NIMI-arvo

Fenkoni (C10H16O) on terpeeneihin kuuluva orgaaninen yhdiste. Yhdistettä voidaan käyttää hajusteissa ja aromiaineena. Fenkoni on kamferin isomeeri. Yhdistettä esiintyy kukkien tuoksuissa ja semiokemikaalina eliöiden viestinnässä.




Sisällysluettelo





  • 1 Ominaisuudet ja esiintyminen luonnossa


  • 2 Valmistus ja käyttö


  • 3 Lähteet


  • 4 Aiheesta muualla




Ominaisuudet ja esiintyminen luonnossa |


Huoneenlämpötilassa fenkoni on väritöntä ja öljymäistä, hieman viskoosia, nestettä. Sen haju on samankaltainen kamferin kanssa. Yhdiste on käytännöllisesti katsoen veteen liukenematonta, mutta liukenee useisiin orgaanisiin liuottimiin kuten etanoliin ja dietyylieetteriin. Fenkoni on optisesti aktiivinen yhdiste ja sen (+)-isomeerin ominaiskiertokyky on +66,8 ja (-)-isomeerin ominaiskiertokyky on -66,8.[2][3][4][5][6]


Fenkonia esiintyy useiden kasvien eteerisissä öljyissä. (+)-isomeeria esiintyy erityisesti fenkolissa (Foeniculum vulgare) ja tupsulaventelissa (Lavandula stoechas). Toista enantiomeeria esiintyy havupuissa esimerkiksi kanadantuijassa (Thuja occidentalis)[5][7]



Valmistus ja käyttö |


Fenkonia valmistetaan lähtemällä pineenistä. Pineeni reagoi karboksyylihappojen kanssa muodostaen fenkyyliestereitä, jotka hydrolysoidaan fenkyylialkoholiksi. Fenkyylialkoholi voidaan tämän jälkeen hapettaa fenkoniksi.[3][4]


Fenkonia käytetään hajusteissa tuomaan tuotteeseen fenkolin tai männyn kaltaista tuoksua. Sitä voidaan myös lisätä elintarvikkeisiin aromiaineeksi. Yhdistettä voidaan käyttää myös eräiden vinyylihartsien liuottimena.[2][3][4][5][6]



Lähteet |



  1. ↑ Fenchone – Substance summary PubChem. NCBI. Viitattu 20.6.2016.


  2. ↑ abcde Alén, Raimo: Kokoelma orgaanisia yhdisteitä: Ominaisuudet ja käyttökohteet, s. 293. Helsinki: Consalen Consulting, 2009. ISBN 978-952-92-5627-3.


  3. ↑ abc Charles S. Sell: Terpenoids, Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2006. Viitattu 20.6.2016


  4. ↑ abc Johannes Panten & Horst Surburg: Flavors and Fragrances, 2. Aliphatic Compounds, Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2015. Viitattu 20.6.2016


  5. ↑ abc Susan Budavari (päätoim.): Merck Index, s. 673. 12th Edition. Merck & Co., 1996. ISBN 0911910-12-3. (englanniksi)


  6. ↑ ab Thomas Scott, Mary Eagleson: Concise encyclopedia chemistry, s. 402. Walter de Gruyter, 1994. ISBN 978-3110114515. (englanniksi)


  7. ↑ K. Husnu Can Baser,Gerhard Buchbauer: Handbook of Essential Oils, s. 262. CRC Press, 2015. ISBN 9781466590472. Teoksen verkkoversio (viitattu 20.6.2016). (englanniksi)



Aiheesta muualla |



  • Royal Society of Chemistry, ChemSpider : Fenchone (englanniksi)


  • Dr. Duke's Phytochemical and Ethnobotanical Databases: Fenchone (englanniksi)


  • Pherobase: Floral Compound - fenchone (englanniksi)


  • Pherobase: Semiochemical - fenchone (englanniksi)


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