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
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, 1,1,6-trimethyl-1,2-dihydronaphthalene 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]

1,1,6-Trimethyl-1,2-dihydronaphthalene is believed to be a degradation product of

β-carotene and lutein.[4] 1,1,6-Trimethyl-1,2-dihydronaphthalene 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 and Dan Johnson (2012). "Aged Riesling and the development of TDN" (PDF). The Australian Wine Research Institute.{{cite web}}: CS1 maint: multiple names: authors list (link)
  6. .