Large-ring lactones from plant oils

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Large-ring lactones from plant oils

Lactones are important intermediates in organic synthesis, and they are employed as monomers and used e.g. as fragrances. Smaller cycles, such as ε-caprolactone, are polymerised to polyesters for medical applications taking advantage of their biodegradability. These small cycles are readily accessible on industrial scales by Baeyer–Villiger oxidation of cyclohexanone. Amongst large-ring lactone...

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Lactones 41. Synthesis and microbial hydroxylation of unsaturated terpenoid lactones with p-menthane ring systems.

Racemic [(±)-4-isopropyl-1-methyl-7-oxa-cis-bicyclo[4.3.0]non-4-en-8-one] and optically active δ,ε-unsaturated lactones [(-)-(1R,6R)-4-isopropyl-1-methyl-7-oxabicyclo[4.3.0]non-4-en-8-one and (+)-(1S,6S)-4-isopropyl-1-methyl-7-oxabicyclo[4.3.0] non-4-en-8-one)] with the p-menthane system were obtained and their odoriferous properties were evaluated. Biotransformations of the racemic lactone wit...

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C-ring cannabinoid lactones: a novel cannabinergic chemotype.

As a part of our controlled-deactivation ligand development project, we recently disclosed a series of (-)-Δ(8)-tetrahydrocannabinols (THCs) with a metabolically labile ester group at the 2'-position of the side chain. Now, we have replaced the C-ring in the classical THC structure with a hydrolyzable seven-membered lactone. One of the synthesized analogues binds with high affinity to the CB1 r...

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Antimicrobial agents from plants: antibacterial activity of plant volatile oils.

The volatile oils of black pepper [Piper nigrum L. (Piperaceae)], clove [Syzygium aromaticum (L.) Merr. & Perry (Myrtaceae)], geranium [Pelargonium graveolens L'Herit (Geraniaceae)], nutmeg [Myristica fragrans Houtt. (Myristicaceae), oregano [Origanum vulgare ssp. hirtum (Link) Letsw. (Lamiaceae)] and thyme [Thymus vulgaris L. (Lamiaceae)] were assessed for antibacterial activity against 25 dif...

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Isolation and characterization of limonoate and nomilinoate A-ring lactones.

A method combining solid-phase extraction and reversed-phase high-performance liquid chromatography is described for the isolation of two key metabolites in the limonoid biosynthetic pathway critical to citrus quality. Potassium salts of limonoate A-ring lactone and nomilinoate A-ring lactone were isolated from young Chandler pummelo seedlings and characterized on the basis of proton and carbon...

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ژورنال

عنوان ژورنال: Green Chemistry

سال: 2013

ISSN: 1463-9262,1463-9270

DOI: 10.1039/c3gc40905h