272122-72-2Relevant articles and documents
Synthesis of enantiomerically pure volatile compounds derived from (R)-3-hydroxynonanal
Kula, Jozef,Quang, Thuat Bui,Sikora, Magdalena
, p. 943 - 950 (2000)
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
Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid
Kula, Józef,Bonikowski, Radoslaw,Szewczyk, Malgorzata,Ciolak, Kornelia
, p. 137 - 141 (2014/07/08)
(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.
Deuterium NMR Used to Indicate a Common Mechanism for the Biosynthesis of Ricinoleic Acid by Ricinus communis and Claviceps purpurea
Billault, Isabelle,Mantle, Peter G.,Robins, Richard J.
, p. 3250 - 3256 (2007/10/03)
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.
