1,1,6-Trimethyl-1,2-dihydronaphthalene

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1,1,6-Trimethyl-1,2-dihydronaphthalene
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
ECHA InfoCard
100.045.577 Edit this at Wikidata
EC Number
  • 250-150-8
UNII
  • InChI=1S/C13H16/c1-10-6-7-12-11(9-10)5-4-8-13(12,2)3/h4-7,9H,8H2,1-3H3
    Key: RTUMCNDCAVLXEP-UHFFFAOYSA-N
  • CC1=CC2=C(C=C1)C(CC=C2)(C)C
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).

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

  1. ^ .
  2. .
  3. .
  4. ^ a b Waterhouse Lab (2016). "TDN, (1,1,6,-trimethyl-1,2-dihydronapthalene)". University of California, Davis.
  5. ^ 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.
  6. .