76835-64-8

Usage

Uses

Used in Organic Synthesis:
Methyl 3-oxododecanoate is used as a synthetic intermediate for the preparation of various organic compounds. Its reactivity and functional groups make it a valuable precursor in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in the Tethered Biginelli Reaction:
In the field of organic chemistry, methyl 3-oxododecanoate is specifically used in the tethered Biginelli reaction for the enantioselective synthesis of batzelladine alkaloids. Batzelladine alkaloids are a class of natural products with diverse biological activities, including anticancer, antiviral, and anti-inflammatory properties. The tethered Biginelli reaction is a multicomponent reaction that allows for the efficient and selective synthesis of these complex molecules, leveraging the unique reactivity of methyl 3-oxododecanoate as a key intermediate.

InChI:InChI=1/C13H24O3/c1-3-4-5-6-7-8-9-10-12(14)11-13(15)16-2/h3-11H2,1-2H3

Upstream product

• 13195-93-2 Ethyl decanoylacetoacetate 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 61058-75-1 3-oxo-dodecanoic acid 
• 112-12-9 methyl nonyl ketone 
• 616-38-6 carbonic acid dimethyl ester 
• 112-31-2 caprinaldehyde 
• 6832-16-2 methyl diazoacetate 
• 111-83-1 1-bromo-octane 
• 105-45-3 acetoacetic acid methyl ester 
• 429675-23-0 5-(1-hydroxydecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 334-48-5 1-decanoic acid 
• 38330-80-2 monomethyl monopotassium malonate 

Downstream Products

• 66997-68-0 (S)-methyl 3-hydroxydodecanoate 
• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 
• 78303-19-2 3-ketododecanoyl-S-CoA 
• 68353-24-2 1-methyl-2-nonyl-4(1H)-quinolone 
• 1391732-33-4 C₂₀H₃₁NO₄ 
• 1391732-32-3 C₂₁H₃₃NO₄ 
• 1391732-31-2 C₂₀H₃₀INO₃ 
• 1391732-30-1 C₂₁H₃₃NO₄ 
• 663884-03-5 N-(3-hydroxyphenyl)-3-oxododecanamide 
• 1391732-24-3 N-(4-methoxyphenyl)-3-oxododecanamide 
• 1391732-23-2 N-(3-iodophenyl)-3-oxododecanamide 
• 1391732-22-1 N-(3-methoxyphenyl)-3-oxododecanamide 
• 1255649-57-0 methyl (Z)-3-(p-toluenesulfonyloxy)-2-dodecenoate 

Relevant academic research and scientific papers

Profiling structural diversity and activity of 2-alkyl-4(1H)-quinoloneN-oxides ofPseudomonasandBurkholderia

We synthesized all major saturated and unsaturated 2-alkyl-4(1H)-quinoloneN-oxides ofPseudomonasandBurkholderia, quantified their native production levels and characterized their antibiotic activities against competingStaphylococcus aureus. We demonstrate that quinolone core methylation and position of unsaturation in the alkyl-chain dictate antibiotic potency which supports the proposed mechanism of action.

COMPOUND FOR USE AGAINST PATHOGENIC NEISSERIA AND HAEMOPHILUS SPECIES AND MORAXELLA CATARRHALIS

The present invention relates to a compound, which can be used in the prevention and treatment of infections with pathogenic Neisseria species, in particular N. gonorrhoeae and N. meningitidis (the gonococcus and the meningococcus, respectively), and other pathogenic bacteria (e.g. Haemophilus species or Moraxella catarrhalis ), and which can be used for disinfecting a substrate from said bacteria. Moreover, the present invention relates to a corresponding pharmaceutical composition comprising said compound.

Quinolones modulate ghrelin receptor signaling: Potential for a novel small molecule scaffold in the treatment of cachexia

Cachexia is a metabolic wasting disorder characterized by progressive weight loss, muscle atrophy, fatigue, weakness, and appetite loss. Cachexia is associated with almost all major chronic illnesses including cancer, heart failure, obstructive pulmonary disease, and kidney disease and significantly impedes treatment outcome and therapy tolerance, reducing physical function and increasing mortality. Current cachexia treatments are limited and new pharmacological strategies are needed. Agonists for the growth hormone secretagogue (GHS-R1a), or ghrelin receptor, prospectively regulate the central regulation of appetite and growth hormone secretion, and therefore have tremendous potential as cachexia therapeutics. Non-peptide GHS-R1a agonists are of particular interest, especially given the high gastrointestinal degradation of peptide-based structures, including that of the endogenous ligand, ghrelin, which has a half-life of only 30 min. However, few compounds have been reported in the literature as non-peptide GHS-R1a agonists. In this paper, we investigate the in vitro potential of quinolone compounds to modulate the GHS-R1a in both transfected human cells and mouse hypothalamic cells. These chemically synthesized compounds demonstrate a promising potential as GHS-R1a agonists, shown by an increased intracellular calcium influx. Further studies are now warranted to substantiate and exploit the potential of these novel quinolone-based compounds as orexigenic therapeutics in conditions of cachexia and other metabolic and eating disorders.

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2-alkyl-4-quinolone N-oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P. aeruginosa, and its structure is shown to be trans-Δ1-2-(non-1-enyl)-4-quinolone N-oxide. This compound is the most active agent against S. aureus, including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small-colony variants of S. aureus, reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P. aeruginosa to modulate competing bacterial species.

Exploiting interkingdom interactions for development of small-molecule inhibitors of candida albicans biofilm formation

A rapid decline in the development of new antimicrobial therapeutics has coincided with the emergence of new and more aggressive multidrug-resistant pathogens. Pathogens are protected from antibiotic activity by their ability to enter an aggregative biofilm state. Therefore, disrupting this process in pathogens is a key strategy for the development of next-generation antimicrobials. Here, we present a suite of compounds, based on the Pseudomonas aeruginosa 2-heptyl-4(1H)-quinolone (HHQ) core quinolone interkingdom signal structure, that exhibit noncytotoxic antibiofilm activity toward the fungal pathogen Candida albicans. In addition to providing new insights into what is a clinically important bacterium-fungus interaction, the capacity to modularize the functionality of the quinolone signals is an important advance in harnessing the therapeutic potential of signaling molecules in general. This provides a platform for the development of potent next-generation small-molecule therapeutics targeting clinically relevant fungal pathogens.

Preparation of the even-numbered 3-oxo fatty acid nicotinyl esters from C6:0 to C18:0

Here, we report a systematic comparison of different methods for the transesterification of 3-oxo fatty acid alkyl esters to the corresponding nicotinyl esters. A simple method producing the target esters in high yields and purity has been developed. Nicotinyl esters are of interest for mass spectrometry analysis of fatty acids. Also, the hydrophilic head group of nicotinyl esters can be used as the basis for the preparation of liposome-building molecules.

A structure activity-relationship study of the bacterial signal molecule HHQ reveals swarming motility inhibition in Bacillus atrophaeus

The sharp rise in antimicrobial resistance has been matched by a decline in the identification and clinical introduction of new classes of drugs to target microbial infections. Thus new approaches are being sought to counter the pending threat of a post-antibiotic era. In that context, the use of non-growth limiting small molecules, that target virulence behaviour in pathogens, has emerged as a solution with real clinical potential. We have previously shown that two signal molecules (HHQ and PQS) from the nosocomial pathogen Pseudomonas aeruginosa have modulatory activity towards other microorganisms. This current study involves the synthesis and evaluation of analogues of HHQ towards swarming and biofilm virulence behaviour in Bacillus atrophaeus, a soil bacterium and co-inhibitor with P. aeruginosa. Compounds with altered C6-C8 positions on the anthranilate-derived ring of HHQ, display a surprising degree of biological specificity, with certain candidates displaying complete motility inhibition. In contrast, anti-biofilm activity of the parent molecule was completely lost upon alteration at any position indicating a remarkable degree of specificity and delineation of phenotype.

Synthesis of β-ketoesters from renewable resources and Meldrum's acid

β-Ketoesters are valuable building blocks for the synthesis of compounds with different biological activities. In this study, a series of fatty β-ketoesters were obtained from fatty acids and Meldrum's acid using N,N-dicyclohexylcarbodiimide and dimethylaminopyridine. In addition, we demonstrate for the first time the synthesis of new fatty β-ketoesters from oleic (cis-C18:1), elaidic (trans-C18:1), ricinoleic (cis-C18:1, 12-OH), linoleic (cis,cis-C18:2), and linolenic (cis,cis,cis-C18:3) acids in good yields.

Unusual acetylation-elimination in the formation of tetronate antibiotics

The identity and reactivity of the intermediates in agglomerin biosynthesis were established and the respective roles of the acetyltransferase Agg4 and the eliminating enzyme Agg5 identified (see scheme). It is proposed that enzymes homologous to Agg4 and

Immunomodulation and the quorum sensing molecule 3-oxo-C 12-homoserine lactone: The importance of chemical scaffolding for probe development

As a guide for chemical probe design, focused analogue synthetic studies were undertaken upon the lactone ring of 3-oxo-C12-homoserine lactone. We have concluded that hydrolytic instability of the heterocyclic ring is pivotal for its ability to modulate immune signaling and probe preparation was aligned with these findings. The Royal Society of Chemistry 2013.