110567-68-5

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 61393-53-1 oleic acid-(4-bromo-phenacyl ester) 
• 112-79-8 Elaidic acid 
• 110551-46-7 trans-9-hydroperoxyoctadec-10-enoic acid 

Relevant academic research and scientific papers

Algicidal hydroxylated C18 unsaturated fatty acids from the red alga Tricleocarpa jejuensis: Identification, synthesis and biological activity

Bioassay-guided separation of a methanol extract of Tricleocarpa jejuensis by monitoring algicidal activity against the red tide phytoplankton Chattonella antiqua led to the isolation of an active fraction consisting of a mixture of four isomeric compounds. The active compounds were identified as (E)-9-hydroxyoctadec-10-enoic acid (1), (E)-10-hydroxyoctadec-8-enoic acid (2), (E)-11-hydroxyoctadec-12-enoic acid (3) and (E)-12-hydroxyoctadec-10-enoic acid (4) by NMR, IR and mass spectral data. The structures were confirmed by comparison of the NMR and MS data with those of authentic samples of 1–4 obtained by unambiguous syntheses. Synthesized hydroxy acids 1–4 and related compounds were assessed for algicidal activity against C. antiqua and it was found that all of 1–4 had high activity (>80% mortality at 24 h) at a concentration of 20 μg/mL. A structure–activity relationship study using 11 related compounds revealed that the presence of the hydroxyl group is important for the activity and the double bond may be replaced with a triple bond.

Oxygenation of monoenoic fatty acids by CYP175A1, an orphan cytochrome P450 from thermus thermophilus HB27

The catalytic activity of CYP175A1 toward monooxygenation of saturated and monounsaturated fatty acids of various chain lengths (C16-C24) has been investigated to assess the enzymatic properties of this orphan thermostable cytochrome P450 enzyme. The resu

Allylic Mono- and Di-hydroxylation of Isolated Double Bonds with Selenium Dioxide-tert-Butyl Hydroperoxide. NMR Characterization of Long-chain Enols, Allylic and Saturated 1,4-Diols, and Enones

Selenium dioxide with tert-butyl hydroperoxide as re-oxidant was used in the allylic hydroxylation of isolated double bonds in straight-chain hydrocarbons.This was shown for mono-unsaturated fatty acids, esters and alcohols.Either allylic position was hydroxylated individually or both positions reacted to give dihydroxy isomers, affording numerous novel hydroxy compounds.Yields of monohydroxy compounds in which the OH group is between the double bond and C-1 were usually higher than those in which the OH group is between the double bond and the methyl terminus.Monohydroxy products were used as starting material in subsequent allylic hydroxylation reactions to increase the yield of dihydroxy product, although this reaction is slow.Coinciding with the known mechanism, cis double bonds of starting materials isomerized nearly quantitatively to trans double bonds in the products while trans double bonds did not isomerize.Resonance differences of the olefinic carbons in 13C NMR of the unsaturated monohydroxy compounds show on which side of the double bond the hydroxy group is located.The magnitude of these differences depends on the nature of the group at C-1 and the distance of the double bond from C-1.Corresponding saturated hydroxy fatty acids were synthesized with the hydrazine-air system. 13C-NMR of the saturated compounds showed that the dihydroxy products were erythro/threo diastereoisomers.With this assignment, 1H NMR of the unsaturated allylic dihydroxy compounds may be used to distinguish these diastereoisomers.The olefinic protons of the erythro dihydroxy diastereoisomer resonate downfield from those of the threo form.The threo diastereoisomers are formed in higher yields than theirerythro counterparts.Compounds with allylic keto group (enones) analogous to the monohydroxy products arose as side products.The 13C NMR spectra of these enones are discussed.

Allylic Hydroperoxide Rearrangement: β-Scission or Concerted Pathway?

The rearrangements of the allylic hydroperoxides derived from oleic acid have been studied.Two hydroperoxides are formed by singlet-oxygen oxidation of oleic acid trans-9-hydroperoxyoctadec-10-enoic acid (5) and trans-10-hydroperoxyoctadec-8-enoic acid (6).These hydroperoxides can be separated by reverse-phase chromatography.Rearrangement of 18O-labeled hydroperoxides (5 or 6) under a 32O2 atmosphere led to no incorporation of 16O into the rearrangement products.Similarly, rearrangement of 16O-labeled hydroperoxides (5 or 6) under a 36O2 atmosphere led to no incorporation of 18O into the rearrangement products.The hydroperoxide 5 rearranges to a mixture of 5 and trans-11-hydroperoxyoctadec-9-enoic acid and alcohols and ketones resulting from Russell termination steps.The results are discussed in terms of a concerted rearrangement of allylic peroxyl radicals proceeding through a five-membered-ring transition state.