1679-53-4Relevant articles and documents
A convenient preparation of 10-hydroxydecanoic acid
Elliger, Carl A.,Diamond
, p. 278 - 278 (1972)
The alkaline cleavage of ricinoleates may be carried out in ethanol at temperatures of 190-200 C using two to three equivalents of NaOH to give yields up to 69% of pure 10-hydroxydecanoic acid. This method avoids the use of large excesses of alkali as well as the use of high boiling alcohols as reaction media.
Molecular cloning of CYP76B9, a cytochrome P450 from Petunia hybrida, catalyzing the ω-hydroxylation of capric acid and lauric acid
Imaishi, Hiromasa,Petkova-Andonova, Mariana
, p. 104 - 113 (2007)
A cDNA encoding a cytochrome P450 (CYP76B9) was isolated from Petunia hybrida. Northern blot analysis revealed preferential expression of the gene in flowers and leaves. The recombinant yeast microsomes expressing CYP76B9 was allowed to react with capric acid and lauric acid as substrates. One major metabolite was produced from each fatty acid after incubation with yeast microsomes expressing CYP76B9. The metabolites were identified by gas chromatography-mass spectrometry (GC-MS) as ω-hydroxy capric acid and ω-hydroxy lauric acid. The kinetic parameters of the reactions were K m = 9:4 μM and Vmax = 13:6 mol min-1 per mol of P450 for capric acid, and Km = 5:7 μM and Vmax = 19:1 mol min-1 per mol of P450 for lauric acid. We found that the ω-hydroxy metabolites of capric acid and lauric acid can affect the plant growth of Arabidopsis thaliana. Plants grown in the presence of ω-hydroxy fatty acids exhibited shorter root length than control plants with the corresponding non-hydroxylated fatty acids.
Novel insights into oxidation of fatty acids and fatty alcohols by cytochrome P450 monooxygenase CYP4B1
Thesseling, Florian A.,Hutter, Michael C.,Wiek, Constanze,Kowalski, John P.,Rettie, Allan E.,Girhard, Marco
, (2019/12/12)
CYP4B1 is an enigmatic mammalian cytochrome P450 monooxygenase acting at the interface between xenobiotic and endobiotic metabolism. A prominent CYP4B1 substrate is the furan pro-toxin 4-ipomeanol (IPO). Our recent investigation on metabolism of IPO related compounds that maintain the furan functionality of IPO while replacing its alcohol group with alkyl chains of varying structure and length revealed that, in addition to cytotoxic reactive metabolite formation (resulting from furan activation) non-cytotoxic ω-hydroxylation at the alkyl chain can also occur. We hypothesized that substrate reorientations may happen in the active site of CYP4B1. These findings prompted us to re-investigate oxidation of unsaturated fatty acids and fatty alcohols with C9–C16 carbon chain length by CYP4B1. Strikingly, we found that besides the previously reported ω- and ω-1-hydroxylations, CYP4B1 is also capable of α-, β-, γ-, and δ-fatty acid hydroxylation. In contrast, fatty alcohols of the same chain length are exclusively hydroxylated at ω, ω-1, and ω-2 positions. Docking results for the corresponding CYP4B1-substrate complexes revealed that fatty acids can adopt U-shaped bonding conformations, such that carbon atoms in both arms may approach the heme-iron. Quantum chemical estimates of activation energies of the hydrogen radical abstraction by the reactive compound 1 as well as electron densities of the substrate orbitals led to the conclusion that fatty acid and fatty alcohol oxidations by CYP4B1 are kinetically controlled reactions.
One-pot ozonolytic synthesis of acyclic α,ω-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol
Legostaeva,Botsman,Nazarov,Yakovleva,Garifullina,Khalikov,Ishmuratov
, p. 935 - 940 (2015/10/12)
Transformations of peroxy products formed by ozonolysis of undecylenic acid derivatives (methyl ester and hydride reduction product, 10-undecen-1-ol) in various protic and aprotic solvents (MeOH, Pr i OH, tetrahydrofuran, 1: 5 AcOH-CH2Cl2 mixture), occurring under the action of such reductants as hydroxylamine and semicarbazide hydrochlorides, were studied. These reductants exhibit high performance and in some cases high chemoselectivity, which allowed the development of a number of one-pot procedures for the synthesis of acyclic α,ω-bifunctional compounds, the majority of which are widely used in medicine, perfumery, cosmetics, engineering, and chemical industry, e.g., as block synthons in targeted organic synthesis.
