Synthese der (3S,4R,3′S,4′R)‐ und (3S,4S,3′S,4′S)Crustaxanthine sowie weiterer Verbindungen mit 3,4‐Dihydroxy‐β‐Endgruppen

Buschor, Daniel Jacques; Eugster, C. H.

doi:10.1002/hlca.19900730426

Cited by 13 publications

(5 citation statements)

References 43 publications

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“…3,4-Diacetoxy-β-ionone ( 28 ) ( cis / trans mixture), was prepared from 3,4-dehydro-β-ionone according to the procedure described by Buschor [51]. The oxidation of 4-keto-β-ionone with IBDA in methanol [52] afforded 3-hydroxy-4-keto-β-ionone that was further oxidated using oxygen in presence of t BuOK [53] to give 3,4-diketo-β-ionone.…”

Section: Methodsmentioning

confidence: 99%

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Serra

Simeis

2018

Molecules

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In this work, we describe a study on the biotransformation of seven natural occurring apocarotenoids by means of eleven selected fungal species. The substrates, namely ionone (α-, β- and γ-isomers), 3,4-dehydroionone, damascone (α- and β-isomers) and theaspirane are relevant flavour and fragrances components. We found that most of the investigated biotransformation reactions afforded oxidized products such as hydroxy- keto- or epoxy-derivatives. On the contrary, the reduction of the keto groups or the reduction of the double bond functional groups were observed only for few substrates, where the reduced products are however formed in minor amount. When starting apocarotenoids are isomers of the same chemical compound (e.g., ionone isomers) their biotransformation can give products very different from each other, depending both on the starting substrate and on the fungal species used. Since the majority of the starting apocarotenoids are often available in natural form and the described products are natural compounds, identified in flavours or fragrances, our biotransformation procedures can be regarded as prospective processes for the preparation of high value olfactory active compounds.

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Section: Methodsmentioning

confidence: 99%

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Serra

Simeis

2018

Molecules

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“…If the C 10 bisphosphonate 708 is used instead of the phosphonium salt 704 , the resulting alkyne is hydrogenated to the cis isomer, and the sequence ends with the isomerization to the trans isomer (Scheme ). Violaxanthin ( 494 ), mimulaxanthin ( 709 ), crustaxanthin ( 710 ), and the nonsymmetrical neoxanthin ( 584 ) have been made with this tactic.…”

Section: Synthesis Of Carotenoidsmentioning

confidence: 99%

Functions, Therapeutic Applications, and Synthesis of Retinoids and Carotenoids

et al. 2013

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“…Dies hat zur Folge, dass bei 3'-Epilutein eine wesentlich starkere Uberlappung der 71 -0rbitale von der Doppelbindung im Ring mit denjenigen der Polyen-Seitenkette eintritt; vgl. [14][15][16][17]. Uberraschend ist, dass sich diese Interaktion vor allem im UV-Bereich auswirkt.…”

Section: *)unclassified

Eine weitere, diesmal erfolgreiche Suche nach 3′‐Epilutein in Pflanzen

Märki‐Fischer

Eugster

1990

Helvetica Chimica Acta

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The 3'-epilutein, an extremely rare carotenoid, found till now in only one plant, was detected in anthers of flowers of several roses and in those of peonies. Das 3'-Epilutein (1) ist im Pflanzenreich bisher erst in Bliiten von Caltha palustris (Sumpfdotterblume) entdeckt worden [2] [3]. Es wird dort begleitet von 3',0-Didehydrolutein (2) und Lutein (3) [4], was darauf hinweist, dass seine Bildung auf einen Dehydrierungs-und (nicht-stereospezifischen) Reduktionsprozess am allylischen OH-C(3) zuriickzufiihren ist. Im Tierreich ist 1 erstmals im Goldfisch (Carassius auratus) aufgefunden worden [5]. Neuere Untersuchungen haben gezeigt, dass 1 und weitere Stereoisomere in Tieren weitverbreitet vorkommen [6]. OH no HO 1 3 0 HO no 2 4

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Synthese der (3S,4R,3′S,4′R)‐ und (3S,4S,3′S,4′S)Crustaxanthine sowie weiterer Verbindungen mit 3,4‐Dihydroxy‐β‐Endgruppen

Cited by 13 publications

References 43 publications

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane

Functions, Therapeutic Applications, and Synthesis of Retinoids and Carotenoids

Eine weitere, diesmal erfolgreiche Suche nach 3′‐Epilutein in Pflanzen

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