25312-34-9Relevant articles and documents
The new halolactones and hydroxylactone with trimethylcyclohexene ring obtained through combined chemical and microbial processes
Grabarczyk, Malgorzata,Maczka, Wanda,Winska, Katarzyna,Zarowska, Barbara,Aniol, Miroslaw
, p. 195 - 203 (2014)
The commercially available racemic (±) α-ionone was used as a substrate for the four-step chemical synthesis of three new γ- halolactones. During these processes known α-ionol and new compounds: γ,δ-unsaturated ester ((6E)-5-(2,6,6-trimethylcyclohex-2-en-1-yl) oct-6-en-3-one) (3) and γ,δ-unsaturated acid ((6E)-3-(2,6,6- trimethylcyclohex-2-en-1-yl)hex-4-enoic acid) (4), were obtained as intermediates. γ,δ-Unsaturated acid was used as a substrate for obtaining also new compounds: 5-(1-chloroethyl)-4-(2,6,6-trimethylcyclohex-2-en- 1-yl)dihydrofuran-2(3H)-one (5), 5-(1-bromo)-4-(2,6,6-trimethylcyclohex-2-en-1- yl)dihydrofuran-2(3H)-one (6) and 5-(1-iodo)-4-(2,6,6-trimethylcyclohex-2-en-1- yl)dihydrofuran-2(3H)-one (7). At the last step these halolactones were converted into the hydroxylactone by microorganisms. Several fungal strains (Fusarium species, Syncephalastrum racemosum, Botrytis cinerea) were tested. Most of the selected microorganisms transformed these lactones by hydrolytic dehalogenation into a new 5-(1-hydroxyethyl)-4-(2,6,6-trimethylcyclohex-2-en-1- yl)dihydrofuran-2(3H)-one (8), mainly the (+) stereoisomer. The hydroxylactone obtained during biotransformation has been examined for its antimicrobial activity against bacteria, yeasts and fungi. It was found that this compound exhibits growth inhibition against some tested microorganisms. The structure of all the substrates and products was established on the basis of their spectral data.
Fungi-mediated biotransformation of the isomeric forms of the apocarotenoids ionone, damascone and theaspirane
Serra, Stefano,De Simeis, Davide
, (2019/01/16)
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.
PRO-FRAGRANCE COMPOUNDS
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Page/Page column 22, (2014/12/09)
A compound of Formula (I) wherein R1 represents a C3 to C20 hydrocarbon group derived from a fragrant alcohol of formula R1OH or from a fragrant aryl aldehyde or ketone of Formula (II), wherein: R2 is, independently, hydrogen atom, hydroxyl group, acetoxy group, -O(C=O)CH(CH3), optionally substituted C1-C6 alkyl group or C1-C6 alkoxy group, wherein any two of R2 may form an optionally substituted 5 or 6 membered ring, and R1 represents a radical derived from a fragrant alcohol of formula R1OH or from a fragrant aldehyde or from a fragrant aryl aldehyde or ketone of formula (II). The compounds are useful for example as a precursor for the prolonged delivery or release of fragrant compounds such as fragrant alcohols or aldehydes.
