1,1,6-Trimethyl-1,2-dihydronaphthalene
Names | |
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IUPAC name
1,1,6-Trimethyl-1,2-dihydronaphthalene
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Other names
1,2-Dihydro-1,1,6-trimethylnaphthalene
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Identifiers | |
3D model (
JSmol ) |
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Abbreviations | TDN |
ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.045.577 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) is 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
- ^ PMID 31908985.
- PMID 22397689.
- S2CID 237596110.
- ^ a b Waterhouse Lab (2016). "TDN, (1,1,6,-trimethyl-1,2-dihydronapthalene)". University of California, Davis.
- ^ Cory Black; Leigh Francis; Prue Henschke; Dimitra Capone; Samantha Anderson; Martin Day; Helen Holt; Wes Pearson; Markus Herderich; Dan Johnson (2012). "Aged Riesling and the development of TDN" (PDF). The Australian Wine Research Institute.
- ISBN 978-1-84549-079-9.