Chemistry:1,1,6-Trimethyl-1,2-dihydronaphthalene

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1,1,6-Trimethyl-1,2-dihydronaphthalene
1,1,6-Trimethyl-1,2-dihydronaphthalene.svg
Names
IUPAC name
1,1,6-Trimethyl-1,2-dihydronaphthalene
Other names
1,2-Dihydro-1,1,6-trimethylnaphthalene
Identifiers
3D model (JSmol)
Abbreviations TDN
ChEBI
ChemSpider
EC Number
  • 250-150-8
UNII
Properties
C13H16
Molar mass 172.271 g·mol−1
Boiling point 115 °C (239 °F; 388 K)
at 18 Torr[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) is an aroma compound present in wine,[1] particularly aged Rieslings.[2][3] 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.[4]

In wines, TDN is generally considered to contribute to a desirable aroma in low concentrations, but an undesirable aroma in higher concentrations.[5] The aroma is commonly described as a petrol note or by the French term goût de pétrole.[6]

TDN is believed to be a degradation product of β-carotene and lutein.[4] TDN can also by synthesized in the laboratory from either of the ionones, α-ionone or β-ionone.[1]

References

  1. ↑ 1.0 1.1 1.2 Dobrydnev, Alexey; Tarasov, Andrii; Müller, Nikolaus; Volovenko, Yulian; Rauhut, Doris; Jung, Rainer (2020). "An optimized method for synthesis and purification of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN)". MethodsX 7: 56–61. doi:10.1016/j.mex.2019.12.009. PMID 31908985. 
  2. ↑ Sacks, Gavin L.; Gates, Matthew J.; Ferry, Francois X.; Lavin, Edward H.; Kurtz, Anne J.; Acree, Terry E. (2012). "Sensory Threshold of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) and Concentrations in Young Riesling and Non-Riesling Wines". Journal of Agricultural and Food Chemistry 60 (12): 2998–3004. doi:10.1021/jf205203b. PMID 22397689. 
  3. ↑ Dein, Melissa; Kerley, Trenton; Munafo, John P. (2021). "Characterization of Odorants in a 10-Year-Old Riesling Wine". Journal of Agricultural and Food Chemistry 69 (38): 11372–11381. doi:10.1021/acs.jafc.1c04196. PMID 34547201. 
  4. ↑ 4.0 4.1 Waterhouse Lab (2016). "TDN, (1,1,6,-trimethyl-1,2-dihydronapthalene)". University of California, Davis. https://waterhouse.ucdavis.edu/whats-in-wine/tdn-116-trimethyl-12-dihydronapthalene. 
  5. ↑ "Aged Riesling and the development of TDN". The Australian Wine Research Institute. 2012. https://www.awri.com.au/wp-content/uploads/Sept-Oct-2012-AWRI-Report.pdf. 
  6. ↑ Owen Bird (2005). Rheingold - The German Wine Renaissance. Arima Publishing. pp. 90–97. ISBN 978-1-84549-079-9. 



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