One‐Pot Synthesis of Substituted Styrenes from Vicinal Dibromoalkanes and Arylboronic Acids.

Тихонов, А. А.; Васильев, А. А.; Chirskaya, M. V.; Стручкова, Марина И.; Merkulova, N. L.; Zlotin, Sergei G.

doi:10.1002/chin.200744038

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“…29 The (E) configuration of compound 4 was thus confirmed. 27,28 GC−MS (EI, 70 eV): 111 (100), 41 (21), 55 (20), 125 (20), 98 (16), 68 (15), 56 (15), 85 (14), 57 (13), 83 (13), 168 (M • + , 2).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

Birk¹,

Fraatz²,

Esch³

et al. 2019

J. Agric. Food Chem.

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Fermentation broths of Ashbya gossypii from the industrial production of riboflavin emit an intense floral, fruity, and nutty smell. Typical Ehrlich pathway products, such as 2-phenylethan-1-ol and 2-/3-methylbutan-1-ol, were detected in large amounts as well as some intensely smelling saturated and unsaturated lactones, e.g., γ-decalactone and γ-(Z)-dodec-6-enlactone. An aroma extract dilution analysis identified 2-phenylethan-1-ol and γ-(Z)-dodec-6-enlactone as the main contributors to the overall aroma, with flavor dilution factors of 32 768. The position of the double bonds of unsaturated lactones was determined by the Paternò–Büchi reaction, and reference compounds that were not available commercially were synthesized to elucidate the structures of the uncommon lactones. The absolute configuration and enantiomeric excess values of the lactones were determined by converting the lactones to their corresponding Mosher’s esters. In addition, the odor impressions and odor thresholds in air were determined.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…γ-(E)-Dec-5-enlactone was synthesized according to the method of Miyakoshi and Tsukasa. 11 (E)-1-Bromohex-1-ene was synthesized according to Tarchini et al 13 and Tikhonov et al 14 The reaction mixture was subsequently purified and analyzed as described above.…”

Section: ■ Introductionmentioning

confidence: 99%

Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

Birk¹,

Fraatz²,

Esch³

et al. 2019

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

One‐Pot Synthesis of Substituted Styrenes from Vicinal Dibromoalkanes and Arylboronic Acids.

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Cited by 1 publication

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Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

Industrial Riboflavin Fermentation Broths Represent a Diverse Source of Natural Saturated and Unsaturated Lactones

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