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1 article(s) from Stepanyuk, Alexey

Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase

Alexey Stepanyuk and
Andreas Kirschning

Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252

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Graphical Abstract

Figure 1: Terpene constituents 1–9 found in geranium and bergamot oils and specified odours of individual com...

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Figure 2: Other selected mono- and sesquiterpenes (10–26) as fragrance materials [6].

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Figure 3: Main constituents of natural iris oil: irone (27).

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Scheme 1: First synthesis of ionone (30) [11].

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Scheme 2: First synthesis of Ambrelux (32) [14].

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Scheme 3: Industrial synthesis of myrcene (1) by pyrolysis of β-pinene (8).

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Scheme 4: First synthesis of Iso E Super^® (33), Iso E Super Plus^® (34) and Georgywood^® (35) as a mixture of i...

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Figure 4: Iso E Super^® region of GC spectra of Molecule 01 (left, 75 €–100 € per 100 mL; march 2019), a low-p...

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Scheme 5: First synthetic route to (−)-Georgywood^® (35) by Corey and Hong [33].

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Scheme 6: First synthetic route to the odour-active (+)-enantiomer of Iso E Super Plus^® (+)-34 [33].

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Scheme 7: Analysis of the isomerisation process and formation of products. Most importantly, Iso E Super^® (33...

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Scheme 8: Isomerisation using additives such as alcohols or carboxylic acids. The product with the γ-position...

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Scheme 9: Iso E Super Plus^® (34) can undergo a third cyclisation to tetrahydrofuran 59 through compound rac-53...

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Figure 5: (Adapted from ref. [8]) Ionone (30, 1893, odour threshold: 0.8 ng L⁻¹), koavone (1982, odour threshold...

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Figure 6: Branched, terpene-like cyclohexene derivatives, that are synthetic fragrance components: 60: Iso da...

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Scheme 10: New unnatural terpenoid 70 from unnatural farnesyl pyrophosphate derivative 69 and comparison with ...

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Review

Published 31 Oct 2019

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Synthetic terpenoids in the world of fragrances: Iso E Super® is the showcase

Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase