5129-59-9

Usage

InChI:InChI=1/C16H32O2/c1-15(2)13-11-9-7-5-4-6-8-10-12-14-16(17)18-3/h15H,4-14H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 2485-71-4 13-methyltetradecanoic acid 
• 117582-43-1 Methyl 13-methyl-12-tetradecenoate 
• 170242-21-4 (2R,3R)-3-Hydroxy-2-(13'-methyltetradecanoylamino)-15-methylhexadecanesulfonic acid 
• 68532-63-8 (11-methoxy-11-oxoundecyl)(triphenyl)phosphonium bromide 
• 2834-05-1 11-bromoundecanoic acid 
• 6287-90-7 11-bromo-undecanoic acid methyl ester 
• 929-33-9 methyl 11-iodoundecanoate 
• 95799-79-4 10-Keto-13-methyltetradecansaeuremethylester 
• 106-79-6 dimethyl sebacate 
• 818-88-2 sebacic acid mono methyl ester 
• 14065-32-8 methyl 10-chloro-10-oxodecanoate 
• 1501-82-2 cyclododecene 
• 2009-59-8 methyl 11-formylundecanoate 

Downstream Products

• 66054-36-2 tunicamycin V 
• 2485-71-4 13-methyltetradecanoic acid 

Relevant academic research and scientific papers

Lutoside: An acyl-1-(Acyl-6'-mannobiosyl)-3-glycerol isolated from the Sponge-associated bacterium Micrococcus luteus

Lutoside, an unusual acyl-1-(acyl-6'-mannobiosyl)-3-glycerol 1 was isolated from the sponge-associated bacterial strain Microccocus luteus. Structure elucidation was performed by spectroscopic analysis and chemical transformations.

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

Structural identification of antibacterial lipids from Amazonian palm tree endophytes through the molecular network approach

A library of 197 endophytic fungi and bacteria isolated from the Amazonian palm tree Astrocaryum sciophilum was extracted and screened for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Four out of five antibacterial ethyl acetate extracts were also cytotoxic for the MRC-5 cells line. Liquid chromatography coupled to tandem mass spectrometry (UPHLC-HRMS/MS) analyses combined with molecular networking data processing were carried out to allow the identification of depsipeptides and cyclopeptides responsible for the cytotoxicity in the dataset. Specific ion clusters from the active Luteibacter sp. extract were also highlighted using an MRSA activity filter. A chemical study of Luteibacter sp. was conducted leading to the structural characterization of eight fatty acid exhibiting antimicrobial activity against MRSA in the tens of μg/mL range.

Synthesis of a maradolipid without using protecting groups

A convenient route has been developed to synthesize 6-O-mono- and 6,6′-di-O-acyl symmetrical and unsymmetrical (un)-symmetrically trehalose derivatives from trehalose using a combination of enzymic and nonenzymic reactions. Thus, a typical maradolipid was accessed in two-steps.

Structures of topostins, DNA topoisomerase I inhibitors of bacterial origin

The structures of topostins, a novel type of mammalian DNA topoisomerase I inhibitors isolated from the bacterium Flexibacter topostinus sp. nov., have remained unknown. Reexamination of the production of topostins resulted in the isolation of original topostins B (B553 (1) and B567 (2)) and new related compounds named topostins D (D640 (3) and D654 (4)). Their structures, including the absolute stereochemistry, were determined by spectroscopic analyses and chemical degradations. These substances are lipid-containing amino acids and peptides.

N-type calcium channel blockers from a marine bacterium, Cytophaga sp. SANK 71996

N-(3-Acyloxyacyl)glycines were isolated as N-type calcium channel blockers from a marine bacterium Cytophaga sp. SANK 71996. The identification and fermentation of the producing strain and structure characterization of N-(3-acyloxyacyl)glycines by spectral analyses and chemical syntheses are described together with their antagonistic activities.

Sulfobacins A and B, novel von Willebrand factor receptor antagonists. II. Structural elucidation

Sulfobacins A and B are novel von Willebrand factor (vWF) receptor antagonists produced by Chryseobacterium sp. NR 2993. The structures of sulfobacins A and B have been determined to be (2R,3R)-3-hydroxy-2-[(R)-3-hydroxy-15-methylhexadecanamido]-15- methylhexadecanesulfonic acid and (2R,3R)-3-hydroxy-15-methyl-2-[13-methyltetradecanamido]- hexadecanesulfonic acid, respectively, by various 2D NMR experiments and by methanolysis. The absolute configurations of the sulfobacins were determined by a modified MOSHER's method. The structures are related to sulfonolipids, major components of the cell envelope of gliding bacteria of the genus Cytophaga.

Synthetic studies of the tunicamycin antibiotics. Preparation of (+)-tunicaminyluracil, (+)-tunicamycin-V, and 5′-epi-tunicamycin-V

A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V). Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.

1-O-(13-Methyl-1-Z-tetradecenyl)-2-O-(13-methyltetradecanoyl)-glycero-3-phospho-ethanolamine, a Plasmalogen from Myxococcus stipitatus

The structure of 1-O-(13-methyl-1-Z-tetradecenyl)-2-O-(13-methyltetradecanoyl)-glycero-3-phospho-ethanolamine isolated from Myxococcus stipitatus has been elucidated. 1H and 13C NMR as well as mass spectral data have been accumulated which allow a ready identification and structure elucidation of compounds of this type. - Keywords: Myxobacteria, Myxococcus stipitatus, Phospholipids, Plasmalogen, Structure Elucidation