Simple and cost-effective synthesis of 5,7,8-deuterium-labelled 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN-D3)

被引：0

作者：

Dobrydnev, Alexey, V ^{[1
,2
]}

Tarasov, Andrii ^{[3
]}

Popova, Maria, V ^{[1
,4
]}

Fritsch, Stefanie ^{[5
]}

Hausmann, Heike ^{[6
]}

Zorn, Holger ^{[7
]}

Volovenko, Yulian M. ^{[1
]}

Rauhut, Doris ^{[5
]}

Jung, Rainer ^{[3
]}

机构：

[1] Taras Shevchenko Natl Univ Kyiv, Lva Tolstoho St 12, UA-01033 Kiev, Ukraine

[2] Enamine Ltd, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[3] Hsch Geisenheim Univ, Dept Enol, Von Lade Str 1, D-65366 Geisenheim, Germany

[4] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany

[5] Hsch Geisenheim Univ, Dept Microbiol & Biochem, Von Lade Str 1, D-65366 Geisenheim, Germany

[6] Justus Liebig Univ Giessen, Inst Organ Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany

[7] Justus Liebig Univ Giessen, Inst Food Chem & Food Biotechnol, Heinrich Buff Ring 17, D-35392 Giessen, Germany

来源：

TETRAHEDRON LETTERS | 2023年 / 128卷

关键词：

Aroma compounds; C; 13-Norisoprenoid; Deuteration; TDN; Wine; BENZENE; DEUTERIUM; COMPLEXES; EXCHANGE; TDN;

D O I：

10.1016/j.tetlet.2023.154692

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an economical and readily scalable synthesis of 1,1,6-trimethyl-1,2-dihydronaphthalene-5,7,8-D-3 (TDN-D-3), a novel deuterium-labeled specimen for stable isotope dilution assay. TDN-D-3 was obtained in four simple steps with 25% overall yield and > 99% chemical purity, starting from commercially available and inexpensive reagents. The described method does not require additional purification procedures (e.g. HPLC or even column chromatography), and the complete synthesis can be performed in three part-time working days.

引用

页数：3

共 7 条

[1] Riesling acetal is a precursor to 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) in wine
Daniel, Merran A.
Capone, Dimitra L.
Sefton, Mark A.
Elsey, Gordon M.
AUSTRALIAN JOURNAL OF GRAPE AND WINE RESEARCH, 2009, 15 (01) : 93 - 96
[2] 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) Sensory Thresholds in Riesling Wine
Tarasov, Andrii
Giuliani, Nicolo
Dobrydnev, Alexey
Schuessler, Christoph
Volovenko, Yulian
Rauhut, Doris
Jung, Rainer
FOODS, 2020, 9 (05)
[3] Absorption of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) from wine by bottle closures
Andrii Tarasov
Nicolò Giuliani
Alexey Dobrydnev
Nikolaus Müller
Yulian Volovenko
Doris Rauhut
Rainer Jung
European Food Research and Technology, 2019, 245 : 2343 - 2351
[4] Absorption of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) from wine by bottle closures
Tarasov, Andrii
Giuliani, Nicolo
Dobrydnev, Alexey
Mueller, Nikolaus
Volovenko, Yulian
Rauhut, Doris
Jung, Rainer
EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2019, 245 (11) : 2343 - 2351
[5] An optimized method for synthesis and purification of 1,1,6-trimethyl-1,2- dihydronaphthalene (TDN)
Dobrydnev, Alexey
Tarasov, Andrii
Mueller, Nikolaus
Volovenko, Yulian
Rauhut, Doris
Jung, Rainer
METHODSX, 2020, 7 : 56 - 61
[6] Sensory Threshold of 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) and Concentrations in Young Riesling and Non-Riesling Wines
Sacks, Gavin L.
Gates, Matthew J.
Ferry, Francois X.
Lavin, Edward H.
Kurtz, Anne J.
Acree, Terry E.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (12) : 2998 - 3004
[7] Petrol Note in Riesling-1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) Selectively Activates Human Odorant Receptor OR8H1
Haag, Franziska
Frey, Tim
Ball, Lena
Hoffmann, Sandra
Krautwurst, Dietmar
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2024, 72 (09) : 4888 - 4896

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