2027-47-6

Usage

Definition

ChEBI: An octadecenoic acid with a double bond at C-9.

InChI:InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)

Upstream product

• 60-29-7 diethyl ether 
• 67-66-3 chloroform 
• 56554-80-4 1-chloro-heptadec-8-ene 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 506-24-1 Stearolic acid 
• 57-11-4 stearic acid 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 110-46-3 isopentyl nitrite 
• 112-91-4 cis-9-octadecenenitrile 
• 122-32-7 trioleoylglycerol 
• 143-28-2 oleoyl alcohol 
• 2423-10-1 Oleic aldehyde 

Downstream Products

• 67081-61-2 oleic acid-(2-phenoxy-ethyl ester) 
• 120-87-6 threo-9,10-dihydroxyoctadecanoic acid 
• 6512-99-8 ethyl oleate 
• 2410-28-8 1-Stearoyl-2,3-dioleoylglycerin 
• 42877-26-9 9,10-dithiocyanato-octadecanoic acid 
• 3839-44-9 17-(3,4-dimethyl-phenyl)-octadecanoic acid 
• 2017-84-7 17-(2-chloro-5-methyl-phenyl)-octadecanoic acid 
• 2017-85-8 17-(4-chloro-3-methyl-phenyl)-octadecanoic acid 
• 124136-57-8 1-(2,4-dichloro-phenoxy)-2-oleoyloxy-ethane 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 31494-22-1 cis-octadec-9-enethiol 
• 120-87-6 erythro-9,10-dihydroxystearic acid 
• 5829-48-1 9,10-dichlorooctadecanoic acid 
• 5829-48-1 (+/-)-9,10-dichlorooctadecanoic acid 

Relevant academic research and scientific papers

Antiparasitic Ovalicin Derivatives from Pseudallescheria boydii, a Mutualistic Fungus of French Guiana Termites

Social insects are in mutualism with microorganisms, contributing to their resistance against infectious diseases. The fungus Pseudallescheria boydii SNB-CN85 isolated from termites produces ovalicin derivatives resulting from the esterification of the less hindered site of the ovalicin epoxide by long-chain fatty acids. Their structures were elucidated using spectroscopic analysis and semisynthesis from ovalicin. For ovalicin, these compounds displayed antiprotozoal activities against Plasmodium falciparum and Trypanosoma brucei, with IC50 values of 19.8 and 1.1 μM, respectively, for the most active compound, i.e., ovalicin linoleate. In parallel, metabolomic profiling of a collection of P. boydii strains associated with termites made it possible to highlight this class of compounds together with tyroscherin derivatives in all strains. Finally, the complete genome of P. boydii strains was obtained by sequencing, and the cluster of potential ovalicin and ovalicin biosynthesis genes was annotated. Through these metabolomic and genomic analyses, a new ovalicin derivative named boyden C, in which the 6-membered ring of ovalicin was opened by oxidative cleavage, was isolated and structurally characterized.

Lipase mimetic cyclodextrins

Glycerophospholipids (GPLs) perform numerous essential functions in biology, including forming key structural components of cellular membranes and acting as secondary messengers in signaling pathways. Developing biomimetic molecular devices that can detect specific GPLs would enable modulation of GPL-related processes. However, the compositional diversity of GPLs, combined with their hydrophobic nature, has made it challenging to develop synthetic scaffolds that can react with specific lipid species. By taking advantage of the host-guest chemistry of cyclodextrins, we have engineered a molecular device that can selectively hydrolyze GPLs under physiologically relevant conditions. A chemically modified α-cyclodextrin bearing amine functional groups was shown to hydrolyze lyso-GPLs, generating free fatty acids. Lyso-GPLs are preferentially hydrolyzed when part of a mixture of GPL lipid species, and reaction efficiency was dependent on lyso-GPL chemical structure. These findings lay the groundwork for the development of molecular devices capable of specifically manipulating lipid-related processes in living systems.

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer

The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.

Biochemical and biophysical characterisation of a small purified lipase from Rhizopus oryzae ZAC3

The characteristics of a purified lipase from Rhizopus oryzae ZAC3 (RoL-ZAC3) were investigated. RoL-ZAC3, a 15.8 kDa protein, which was optimally active at pH 8 and 55 °C had a half-life of 126 min at 60 °C. The kinetic parameters using p-nitrophenylbuty

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.

Homogeneous catalytic hydrogenation of lipids in aqueous dispersions and bacterial cell membranes with an efficient water-soluble Pd(II)-sulfosalan catalyst, Na2[Pd(HSS)]

The recently synthesized water-soluble Na2[Pd(HSS)] (Na2HSS = hydrogenated sulfonated salen) was shown to be a non-toxic, active catalyst for modification of model and biomembranes by homogeneous catalytic hydrogenation. Hydrogenation of the unsaturated fatty acyl residues in soy-bean lecithin liposomes and in biomembranes of intact Pseudomonas putida F1 cells was accompanied by substantial cis-trans isomerization around the C[dbnd]C double bonds. The hydrogenations could be run in aqueous media under mild conditions (25 °C, 1 bar H2). Partial saturation (up to 10% conversion) of the membrane lipids of P. putida F1 did not damage the cells.

Identification and α -Glucosidase Inhibitory Activity of Meroterpenoids from Hericium erinaceus

Hericium erinaceus is a very popular edible and medicinal mushroom used for the treatment of enervation and gastrointestinal diseases in Eastern Asia. Chemical investigation on the fruiting body of Hericium erinaceus led to the isolation of 4 new (1 - 4) and 10 known meroterpenoids (5 - 14). The structures of new compounds were determined via analysis of NMR and MS data in combination with chemical derivatization. The inhibitory activities of 1 - 14 against α -glucosidase were evaluated using p -nitrophenyl- α -D-glucopyranoside, sucrose, or maltose as substrate. Compounds 6, 9, 11 - 13 were demonstrated to show the α -glucosidase inhibitory activities. This work confirms the potential of H. erinaceus in the treatment of diabetes.

Alteration of Chain Length Selectivity of Candida antarctica Lipase A by Semi-Rational Design for the Enrichment of Erucic and Gondoic Fatty Acids

Biotechnological strategies using renewable materials as starting substrates are a promising alternative to traditional oleochemical processes for the isolation of different fatty acids. Among them, long chain mono-unsaturated fatty acids are especially interesting in industrial lipid modification, since they are precursors of several economically relevant products, including detergents, plastics and lubricants. Therefore, the aim of this study was to develop an enzymatic method in order to increase the percentage of long chain mono-unsaturated fatty acids from Camelina and Crambe oil ethyl ester derivatives, by using selective lipases. Specifically, the focus was on the enrichment of gondoic (C20:1 cisΔ11) and erucic acid (C22:1 cisΔ13) from Camelina and Crambe oil derivatives, respectively. The pursuit of this goal entailed several steps, including: (i) the choice of a suitable lipase scaffold to serve as a protein engineering template (Candida antarctica lipase A); (ii) the identification of potential amino acid targets to disrupt the binding tunnel at the adequate location; (iii) the design, creation and high-throughput screening of lipase mutant libraries; (iv) the study of the selectivity towards different chain length p-nitrophenyl fatty acid esters of the best hits found, as well as the analysis of the contribution of each amino acid change and the outcome of combining several of the aforementioned residue alterations and, finally, (v) the selection and application of the most promising candidates for the fatty acid enrichment biocatalysis. As a result, enrichment of C22:1 from Crambe ethyl esters was achieved either, in the free fatty acid fraction (wt, 78%) or in the esterified fraction (variants V1, 77%; V9, 78% and V19, 74%). Concerning the enrichment of C20:1 when Camelina oil ethyl esters were used as substrate, the best variant was the single mutant V290W, which doubled its content in the esterified fraction from approximately 15% to 34%. A moderately lower increase was achieved by V9 and its two derived triple mutant variants V19 and V20 (27%). (Figure presented.).

Light-Driven Enzymatic Decarboxylation of Fatty Acids

The photoenzymatic decarboxylation of fatty acids to alkanes is proposed as an alternative approach for the synthesis of biodiesel. By using a recently discovered photodecarboxylase from Chlorella variabilis NC64A (CvFAP) we demonstrate the irreversible preparation of alkanes from fatty acids and triglycerides. Several fatty acids and their triglycerides are converted by CvFAP in near-quantitative yield and exclusive selectivity upon illumination with blue light. Very promising turnover numbers of up to 8000 were achieved in this proof-of-concept study.

Revealing the Roles of Subdomains in the Catalytic Behavior of Lipases/Acyltransferases Homologous to CpLIP2 through Rational Design of Chimeric Enzymes

The lipases/acyltransferases homologous to CpLIP2 of Candida parapsilosis efficiently catalyze acyltransfer reactions in lipid/water media with high water activity (aW>0.9). Two new enzymes of this family, CduLAc from Candida dubliniensis and CalLAc8 from Candida albicans, were characterized. Despite 82 % sequence identity, the two enzymes have significant differences in their catalytic behaviors. In order to understand the roles played by the different subdomains of these proteins (main core, cap and C-terminal flap), chimeric enzymes were designed by rational exchange of cap and C-terminal flap, between CduLAc and CalLAc8. The results show that the cap region plays a significant role in substrate specificity; the main core was found to be the most important part of the protein for acyltransfer ability. Similar exchanges were made with CAL-A from Candida antarctica, but only the C-terminal exchange was successful. Yet, the role of this domain was not clearly elucidated, other than that it is essential for activity.