6287-90-7

Usage

Uses

Used in Chemical Synthesis:
METHYL 11-BROMOUNDECANOATE is used as a reactant for synthesizing a variety of chemical compounds, including:
1. Methyl 11-(2,5-dibromophenoxy)undecanoate: METHYL 11-BROMOUNDECANOATE is employed as a precursor to prepare acetylenic cyclophanes, which are complex organic molecules with potential applications in materials science and pharmaceutical chemistry.
2. Methyl 11-[(1-phenyl-1H-tetrazol-5-yl)thio]undecanoate: This key intermediate is used in the synthesis of emmyguyacins side chain, which is a component of certain natural products with potential biological activities.
3. Betain derivatives of 11-bromoundecanoic acid: These compounds are explored as potential microbial agents, indicating their possible use in the development of new antimicrobial agents or biocides.

InChI:InChI=1/C12H23BrO2/c1-15-12(14)10-8-6-4-2-3-5-7-9-11-13/h2-11H2,1H3

Upstream product

• 111-81-9 Methyl 10-undecenoate 
• 2834-05-1 11-bromoundecanoic acid 
• 186581-53-3 diazomethane 
• 24724-07-0 methyl 11-hydroxyundecanoate 
• 15949-84-5 11-bromoundecanoyl chloride 
• 112-38-9 10-undecenoic acid 
• 57467-59-1 2E,5E,10-undecatrien-1-oic acid methyl ester 
• 74198-06-4 methyl 11-hydroxyundeca-2E,5E-dienoate 
• 2041-15-8 1,3,5-cyclohexanetriol 
• 67-56-1 methanol 

Downstream Products

• 134701-89-6 11-(3,4,5-Triphenyl-pyrazol-1-yl)-undecanoic acid methyl ester 
• 78277-45-9 methyl 2-phenylselenenyl-11-bromoundecanoate 
• 121942-38-9 12,12-Bis-benzenesulfonyl-dodecanoic acid methyl ester 
• 86560-34-1 12-Isocyano-12-(toluene-4-sulfonyl)-triacontanoic acid methyl ester 
• 1731-86-8 methyl undecanoate 
• 111-81-9 Methyl 10-undecenoate 
• 37973-85-6 methyl (E) 9-undecenoate 
• 344875-96-3 11-(2-Formylphenoxy)undecansaeure-methylester 
• 165590-31-8 methyl 11-(4-chloro-phenylthio)-undecanoate 
• 254966-03-5 methyl 3,5-bis(10-methoxycarbonyldecyloxy)-4-methylbenzoate 
• 412301-54-3 11-[3-(3-trifluoromethyl-3H-diazirin-3-yl)-phenoxy]-undecanoic acid methyl ester 
• 613257-46-8 4-(10-(methoxycarbonyl)decyloxy)benzaldehyde 
• 773877-25-1 11-(bis-benzyloxy-phosphoryl)-undecanoic acid methyl ester 
• 869376-48-7 11-(4-hexyl-3-hydroxyphenoxy)undecanoic acid methyl ester 

Relevant academic research and scientific papers

Design and synthesis of a novel corrosion inhibitor embedded with quaternary ammonium, amide and amine motifs for protection of carbon steel in 1 M HCl

Methyl 11-bromoundecanoate [Br (CH2)10CO2Me] (1) on treatment with tripropylamine gave quaternary salt [Pr3N+(CH2)10CO2Me]Br? (2) which on treatment with diethylenetriamine afforded [Pr3N+(CH2)10CONH(CH2)2NH(CH2)2NH2] Br? (3) containing inhibitive motifs of ammonium, amide and amine motifs embedded in a single frame. The precursor salt 2 and its derivative 3 were successfully synthesized in excellent yields and characterized using different spectroscopic techniques. For the first time, a detailed study on the corrosion inhibition behavior of corrosion inhibitors 2 and 3 for mild steel in 1 M HCl was carried out using electrochemical measurements and comprehensive computational analysis. Both the studied inhibitors showed excellent aqueous solubility. The high inhibition efficiency of 91percent and 93percent at a concentration of 200 mg L?1 was obtained for corrosion inhibitors 2 and 3, respectively. The adsorption of the corrosion inhibitors exhibited the Langmuir isotherm with a mixture of physical and chemical modes of adsorption. The impedance studies showed a rise in the polarization resistance with increasing concentration of the inhibitors. Polarization measurements demonstrated that the inhibitors displayed a mixed-mode of inhibition with primarily cathodic nature. Surface analytical studies supported the inhibitor adsorption and a protective film formation on the carbon steel surface, which improved the surface smoothness of the steel surface. The DFT based quantum chemical calculations supported the experimentally obtained results and showed that the inhibitor 3 displays superior inhibition in comparison to the inhibitor 2. The Monte Carlo simulations revealed higher adsorption energy for the inhibitor 3 compared to 2.

Synthesis, characterization, antimicrobial and biofilm inhibitory activities of new N-oxide esters

Novel N-oxide esters were synthesized from tertiary amine esters, which in turn were obtained from the reaction of 11-bromoundecanoic acid and different alkyl amines. The synthesized N-oxide esters were characterized by fourier transform infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, and mass spectral analysis. The synthetic route involved three steps; initially, 11-bromoundecanoic acid was converted into methyl 11-bromoundecanoate, which was further converted into tertiary amine (mono and di) esters by reacting with different aliphatic amines (hexyl, dodecyl, octadecyl, dioctyl, and dicyclohexyl amine). Finally, the obtained amine esters were converted into N-oxide esters by treating with m-chloroperbenzoic acid. The synthesized N-oxide esters (4a–e) were studied for their antimicrobial and anti-biofilm activities. Among all the synthesized N-oxide esters, compounds 4a and e showed good antimicrobial activity especially towards pathogenic gram-positive bacterial strains with minimum inhibitory concentration values in the range of 7.8–31.2 μg mL?1. The compounds which exhibited antimicrobial activity were also effective in anti-biofilm activity and it was found that the compound 4e exhibited promising biofilm inhibitory activity with IC50 value of 6.4 μg mL?1 against Bacillus subtilis MTCC 121. Further, compound 4e showed increased levels of intracellular reactive oxygen species accumulation, which may be contributing to the bactericidal activity in B. subtilis MTCC 121.

SYNTHESIS AND CONFORMATION OF A BILIRUBIN ANALOG WITH PROPIONIC ACID SIDE CHAINS EXTENDED TO UNDECANOIC ACID

A lipophilic analog of bilirubin with propionic acid groups replaced by undecanoic acid groups (1), was synthesized from 11-bromo-undecanoic acid.UV-visible and NMR spectroscopic analyses suggest reduced intramolecular H-bonding and a preference for a helical conformation.Molecular dynamics computations predict a global energy minimum for a helical porphyrin-like conformation with unusual distorted structures when H-bonding is invoked.Circular dichroism of the pigment complex with human serum albumin gives a bilirubin-like bisignate Cotton effect: Δεmax449 = + 33, Δεmax396 = 47.

BRANCHED CHAIN MONO-GLYCEROL ETHERS FROM A TAIWANESE MARINE SPONGE OF THE GENUS Aaptos

3-(13-Methylhexadecyloxy)-1,2-(S)-propanediol (6) and 3-(15-methyloctadecyloxy)-1,2-(S)-propanediol (7) were isolated from Aaptos species of marine sponge from Taiwanese waters and characterized by spectroscopic methods.Homolog 6 was independently synthesized.

Synthesis, characterization, antimicrobial and biofilm inhibitory studies of new esterquats

Novel esterquats (monoesterquats and diesterquats) were synthesized from 11-bromo undecanoic acid (11-BUA) and different alkyl amines. The prepared compounds were characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. 11-BUA was converted into methyl 11-bromo undecanoate which was further converted into amine ester (amine monoester and diester) by reacting with different aliphatic amines (hexyl, dodecyl, octadecyl, dioctyl and dicyclohexyl amine). Finally, the obtained amine esters were converted into esterquats (monoesterquat and diesterquat) by reacting with methyl iodide followed by ion exchange to afford chloride counter ion esterquats (5a-h). The synthesized esterquat products were studied for their antimicrobial and biofilm inhibitory activities. Among all the compounds, amine ester 3a and esterquat 5d showed potent antimicrobial activity towards pathogenic Gram-positive bacterial strains with minimum inhibitory concentration (MIC) values in the range of 3.9-15.6 μg mL-1 and 1.9-7.8 μg mL-1, respectively. The esterquat 5d also showed promising antifungal activity against Candida albicans MTCC 3017, Candida albicans MTCC 4748 and Candida aaseri MTCC 1962 strains with MIC value of 7.8 μg mL-1 which was identical to standard Miconazole. The compounds which exhibited antimicrobial activity were also effective in anti-biofilm activity and it was found that compound 5d exhibited excellent biofilm inhibitory activity with IC50 value of 0.9 μg mL-1 against Staphylococcus aureus MLS16 MTCC 2940.

Synthesis, characterization, antimicrobial and anti-biofilm activity of a new class of 11-bromoundecanoic acid-based betaines

Novel betaines were synthesized from esterquats, which in turn were obtained from the reaction of 11-bromo undecanoic acid, different alkyl amines, and methyl iodide. The synthesized betaines were characterized by fourier transform infrared, proton nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, and mass spectral analysis. These betaines were synthesized in four steps; in the first step, 11-bromo undecanoic acid was converted into methyl 11-bromoundecanoate followed by the synthesis of secondary amine monoester, and tertiary amine mono and diesters by the reaction of 11-bromoundecanoate with different aliphatic amines (hexyl, dodecyl, octadecyl, dioctyl, and dicyclohexyl amine). In the third step, the prepared secondary amine monoesters, tertiary amine mono, and diesters were converted into monoesterquats and diesterquats by reacting with methyl iodide. The resultant esterquats were converted into betaines by saponification reaction using LiOH.H2O in water and tetrahydrofuran. The synthesized compounds (5a–h) were studied for their antimicrobial activity. Some of the compounds showed good to moderate antibacterial activity with minimum inhibitory concentration values ranging between 3.9–31.2 μg mL?1 and antifungal activity with minimum inhibitory concentration values ranging between 7.8–62.4 μg mL?1. Further, some of the betaines also showed good anti-biofilm activity with IC50 values ranging between 2.1–25.3 μg mL?1 on the tested pathogenic microbial and fungal strains.

Studies in Lipid Mimics. Synthesis and Carbon-13 Relaxation Time Measurements (T1 Values) of Methyl Esters of ω-(2-Anthryl)alkanoic Acids

The syntheses of methyl 12-(2-anthryl)dodecanoate, methyl 14-(2-anthryl)tetradecanoate, and methyl 17-(2-anthryl)heptadecanoate have been achieved.Both 1H and 13C chemical shifts and T1 values for carbons in the systems have been recorded.By using selected heteronuclear decoupling and performing heteronuclear correlated 2-dimensional (HETCOR-2-D) experiments, it was possible to assign protons to specific carbons in most cases.

IDEBENONE COMPOUNDS

The present application provides idebenone derivatives or analogues useful for treating a disease or disorder in a subject in need thereof. Pharmaceutical compositions comprising the compounds and methods of treating the disease or disorder are also provided.

Expansion of the structure-activity relationship of branched chain fatty acids: Effect of unsaturation and branching group size on anticancer activity

Branched chain fatty acids (BCFAs) are a class of fatty acid with promising anticancer activity. The BCFA 13-methyltetradecanoic acid (13-MTD) inhibits tumour growth in vivo without toxicity but efficacy is limited by moderate potency, a property shared b

Total Synthesis of Emmyguyacins A and B, Potential Fusion Inhibitors of Influenza Virus

Fungal glycolipids emmyguyacins A and B inhibit the pH-dependent conformational change of hemaglutinin A during replication of the Influenza virus. Herein, we report the first total synthesis and structure confirmation of emmyguyacins A and B. Our efficient route, which involves regioselective functionalization of trehalose, allows rapid access to adequate amounts of chemically pure emmyguyacin analogues including the desoxylate derivatives for SAR studies.