- Synthesis of enantiomerically pure volatile compounds derived from (R)-3-hydroxynonanal
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Practical preparations of enantiomerically pure R-configured 3-hydroxynonanal dimethyl acetal, 3-acetoxynonanal dimethyl acetal, methyl 3-acetoxynonanoate, δ-undecalactone, 1,3-nonanediol and its esters, 1,4-decanediol and its esters and 2-hexyltetrahydro
- Kula, Jozef,Quang, Thuat Bui,Sikora, Magdalena
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- Chiral amide derivatives of ricinoleic acid and 3-hydroxynonanoic acid synthesis and cytotoxic activity
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A series of chiral ricinoleic and 3-hydroxynonanoic acid derivatives were synthesized in this study using various chemical and biochemical procedures. An effective method for preparation of methyl esters of 3-hydroxynonanoic acid from castor oil or methyl ricinoleate by ozonolysis and oxidation was developed. Simple, fast, and efficient procedures were applied to obtain different primary and secondary, cyclic and acyclic amides, including hydroxamic acids. Among 24 synthesized derivatives of ricinoleic and 3-hydroxynonanoic acids, i.e., methyl esters, amides, and hydroxamic acids, 16 compounds were obtained and described for the first time. The synthesized compounds showed activity against the tested cancer cells, but the best cytotoxic effect was observed for hydroxamic acid derived from 3-hydroxynonanoic acid (11) against HeLa cells. In general, most of the tested compounds were more toxic against HT29 than HeLa cancer cells. The results also showed that there was no significant difference between activities of (R)- and (S)-enantiomer of particular derivatives.
- Matysiak, Sylwia,Kula, Józef,B?aszczyk, Alina
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- Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid
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(R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products.
- Kula, Józef,Bonikowski, Radoslaw,Szewczyk, Malgorzata,Ciolak, Kornelia
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p. 137 - 141
(2014/07/08)
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- Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXVIII. Investigation of transformations of peroxide products of olefins ozonolysis treated with hydroxylamine hydrochloride
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Hydroxylamine hydrochloride efficiently reduces peroxide products of olefins ozonolysis into carbonyl compounds. Depending on the substrate character, solvent, and the treatment conditions the arising aldehydes transformed along the route aldehyde→aldoxime→nitrile→ester into individual compounds or their mixtures, or give the corresponding acetals.
- Ishmuratov,Shayakhmetova,Yakovleva,Legostaeva,Shitikova,Galkin,Tolstikov
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p. 1114 - 1119
(2008/03/11)
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- Deuterium NMR Used to Indicate a Common Mechanism for the Biosynthesis of Ricinoleic Acid by Ricinus communis and Claviceps purpurea
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Previous studies have shown that ricinoleic acid from castor bean oil of Ricinus communis is synthesized by the direct hydroxyl substitution of oleate, while it has been proposed that ricinoleate is formed by hydration of linoleate in the ergot fungus Claviceps purpurea. The mechanism of the enzymes specific to ricinoleate synthesis has not yet been established, but hydroxylation and desaturation of fatty acids in plants apparently involve closely related mechanisms. As mechanistic differences in the enzymes involved in the biosynthesis of natural products can lead to different isotopic distributions in the product, we could expect ricinoleate isolated from castor or ergot oil to show distinct 2H distribution patterns. To obtain information concerning the substrate and isotope effects that occur during the biosynthesis of ricinoleate, the site-specific natural deuterium distributions in methyl ricinoleate isolated from castor oil and in methyl ricinoleate and methyl linoleate isolated from ergot oils have been measured by quantitative 2H NMR. First, the deuterium profiles for methyl ricinoleate from the plant and fungus are equivalent. Second, the deuterium profile for methyl linoleate from ergot is incompatible with this chemical species being the precursor of methyl ricinoleate. Hence, it is apparent that 12-hydroxylation in C. purpurea is consistent with the biosynthetic mechanisms proposed for R. communis and is compatible with the general fundamental mechanistic similarities between hydroxylation and desaturation previously proposed for plant fatty acid biosynthesis.
- Billault, Isabelle,Mantle, Peter G.,Robins, Richard J.
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p. 3250 - 3256
(2007/10/03)
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