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1,1,6-Trimethyl-1,2-dihydronaphthalene
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1,1,6-Trimethyl-1,2-dihydronaphthalene.svg 200px 1,1,6-Trimethyl-1,2-dihydronaphthalene 1,2-Dihydro-1,1,6-trimethylnaphthalene TDN 30364-38-6 correct CAS 89773 108567 250-150-8 121677 01HD1KNX99 1S/C13H16/c1-10-6-7-12-11(9-10)5-4-8-13(12,2)3/h4-7,9H,8H2,1-3H3 RTUMCNDCAVLXEP-UHFFFAOYSA-N CC1=CC2=C(C=C1)C(CC=C2)(C)C
13 16 115 at 18 Torr 10.1016/j.mex.2019.12.009 An optimized method for synthesis and purification of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2020 Dobrydnev Alexey Tarasov Andrii Müller Nikolaus Volovenko Yulian Rauhut Doris Jung Rainer MethodsX 7 56–61 100768 31908985 6938800
1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) is an aroma compound present in wine, particularly aged Rieslings. 10.1021/jf205203b Sensory Threshold of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) and Concentrations in Young Riesling and Non-Riesling Wines 2012 Sacks Gavin L. Gates Matthew J. Ferry Francois X. Lavin Edward H. Kurtz Anne J. Acree Terry E. Journal of Agricultural and Food Chemistry 60 12 2998–3004 22397689 2012JAFC...60.2998S 10.1021/acs.jafc.1c04196 Characterization of Odorants in a 10-Year-Old Riesling Wine 2021 Dein Melissa Kerley Trenton Munafo John P. Journal of Agricultural and Food Chemistry 69 38 11372–11381 34547201 2021JAFC...6911372D 237596110 Chemically, it is classified as a 13C-norisoprenoid, as it has thirteen carbon atoms, and is derived from an isoprenoid by the loss of methylene groups. https://waterhouse.ucdavis.edu/whats-in-wine/tdn-116-trimethyl-12-dihydronapthalene TDN, (1,1,6,-trimethyl-1,2-dihydronapthalene) Waterhouse Lab University of California, Davis 2016
In wines, TDN is generally considered to contribute to a desirable aroma in low concentrations, but an undesirable aroma in higher concentrations. https://www.awri.com.au/wp-content/uploads/Sept-Oct-2012-AWRI-Report.pdf Aged Riesling and the development of TDN Cory Black Leigh Francis Prue Henschke Dimitra Capone Samantha Anderson Martin Day Helen Holt Wes Pearson Markus Herderich Dan Johnson The Australian Wine Research Institute 2012 The aroma is commonly described as a petrol note or by the French term goût de pétrole. Owen Bird Rheingold - The German Wine Renaissance Arima Publishing 2005 90–97 978-1-84549-079-9
TDN is believed to be a degradation product of β-carotene and lutein. TDN can also by synthesized in the laboratory from either of the ionones, α-ionone or β-ionone.
References
Category:Flavors
Category:Terpenes and terpenoids
Category:Oenology
Category:Dialins