Tyrosol
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| Allgemeines | ||||||||||||||||||||||
| Name | Tyrosol | |||||||||||||||||||||
| Summenformel | C8H10O2 | |||||||||||||||||||||
| Kurzbeschreibung |
weißes bis gelbliches Pulver[1] | |||||||||||||||||||||
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| Eigenschaften | ||||||||||||||||||||||
| Molare Masse | 138,16 g·mol−1 | |||||||||||||||||||||
| Aggregatzustand |
fest[1] | |||||||||||||||||||||
| Schmelzpunkt | ||||||||||||||||||||||
| Siedepunkt |
310 °C[1] | |||||||||||||||||||||
| Löslichkeit |
löslich in Wasser, Methanol, Benzol, Aceton, Chloroform und Ethanol[1] | |||||||||||||||||||||
| Sicherheitshinweise | ||||||||||||||||||||||
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| Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa). | ||||||||||||||||||||||
Tyrosol ist ein phenolischer Naturstoff.
Vorkommen
Tyrosol kommt beispielsweise in Olivenöl[2][3][4] und Wein vor.[3][4] Es ist außerdem in den Wurzeln des Rosenwurz enthalten.[5] Im menschlichen Metabolismus wird aus Tyramin gebildet.[3] Es kommt auch als Nebenprodukt in Gärungsprozessen durch Hefen vor.[6] Bei Candida albicans dient die Verbindung dem Quorum Sensing.[7]
Biosynthese
Die Biosynthese durch Saccharomyces cerevisiae geht von Tyrosin aus.[6]
Eigenschaften
In verschiedenen Studien konnten antioxidative und entzündungshemmende Eigenschaften festgestellt werden.[4][8]
Verwendung
Tyrosol wird als Aromastoff verwendet und ist in der EU unter der FL-Nummer 02.166 für Lebensmittel allgemein zugelassen.[9]
Einzelnachweise
- ↑ a b c d e f g Eintrag zu 2-(4-Hydroxyphenyl)ethanol, >98.0% bei TCI Europe, abgerufen am 22. Oktober 2023.
- ↑ Concepción Romero, Manuel Brenes: Analysis of Total Contents of Hydroxytyrosol and Tyrosol in Olive Oils. In: Journal of Agricultural and Food Chemistry. Band 60, Nr. 36, 12. September 2012, S. 9017–9022, doi:10.1021/jf3026666.
- ↑ a b c Jose Rodríguez-Morató, Anna Boronat, Aristotelis Kotronoulas, Mitona Pujadas, Antoni Pastor, Eulalia Olesti, Clara Pérez-Mañá, Olha Khymenets, Montserrat Fitó, Magí Farré, Rafael de la Torre: Metabolic disposition and biological significance of simple phenols of dietary origin: hydroxytyrosol and tyrosol. In: Drug Metabolism Reviews. Band 48, Nr. 2, 2. April 2016, S. 218–236, doi:10.1080/03602532.2016.1179754.
- ↑ a b c Ioanna C. Vlachogianni, Elizabeth Fragopoulou, Ioannis K. Kostakis, Smaragdi Antonopoulou: In vitro assessment of antioxidant activity of tyrosol, resveratrol and their acetylated derivatives. In: Food Chemistry. Band 177, Juni 2015, S. 165–173, doi:10.1016/j.foodchem.2014.12.092.
- ↑ Pham Tuan Linh, Young Ho Kim, Seon Pyo Hong, Jiang Ji Jian, Jong Seong Kang: Quantitative determination of salidroside and tyrosol from the underground part of Rhodiola rosea by high performance liquid chromatography. In: Archives of Pharmacal Research. Band 23, Nr. 4, August 2000, S. 349–352, doi:10.1007/BF02975446.
- ↑ a b S. Sentheshanmuganathan, S. R. Elsden: The mechanism of the formation of tyrosol by Saccharomyces cerevisiae. In: Biochemical Journal. Band 69, Nr. 2, 1. Juni 1958, S. 210–218, doi:10.1042/bj0690210.
- ↑ Mohammed A. S. Alem, Mohammed D. Y. Oteef, T. Hugh Flowers, L. Julia Douglas: Production of Tyrosol by Candida albicans Biofilms and Its Role in Quorum Sensing and Biofilm Development. In: Eukaryotic Cell. Band 5, Nr. 10, Oktober 2006, S. 1770–1779, doi:10.1128/EC.00219-06, PMID 16980403, PMC 1595342 (freier Volltext).
- ↑ Mark B. Plotnikov, Tatiana M. Plotnikova: Tyrosol as a Neuroprotector: Strong Effects of a “Weak” Antioxidant. In: Current Neuropharmacology. Band 19, Nr. 4, April 2021, S. 434–448, doi:10.2174/1570159X18666200507082311, PMID 32379590, PMC 8206466 (freier Volltext).
- ↑ Food and Feed Information Portal Database | FIP. Abgerufen am 22. Oktober 2023.
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