173074-89-0

Upstream product

• 134834-32-5 12-(benzyloxy)dodecan-1-ol 
• 5675-51-4 1,12-dodecandiol 
• 100-39-0 benzyl bromide 

Downstream Products

• 173074-90-3 1-(12'-Benzyloxydodecyl)-1-ethoxycyclopropane 
• 910631-00-4 (E)-14-Benzyloxy-tetradec-2-enoic acid ethyl ester 
• 56909-04-7 14-Pentadecynoic acid, methyl ester 
• 910630-96-5 (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-Pentakis-benzyloxy-25-((R)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-17-hydroxy-pentacos-14-ynoic acid 
• 910630-86-3 (17R,18S,19S,20S,21S,22S)-18,19,20,21,22-Pentakis-benzyloxy-25-((S)-1-tert-butoxycarbonyl-2-methyl-propylcarbamoyl)-17-hydroxy-pentacos-14-ynoic acid 
• 910630-95-4 C₇₉H₁₁₃NO₁₁Si 
• 910630-80-7 C₇₉H₁₁₃NO₁₁Si 
• 212913-84-3 Pentadec-14-in-saeure 
• 50515-98-5 14-hydroxytetradecanoic acid methyl ester 
• 1618082-04-4 ((12-fluorotetradecyloxy)methyl)benzene 
• 1618082-03-3 14-(benzyloxy)tetradecan-3-ol 

Relevant academic research and scientific papers

Total Synthesis of the Anticancer Marine Natural Product Mycalol

This communication describes a synthetic study of the originally proposed structure of mycalol (1) and the total synthesis of the actual structure of the anticancer marine natural product mycalol (2). The total synthesis of the originally proposed structu

BIPOLAR TETRAETHER LIPIDS

Disclosed herein, inter alia, are compounds, compositions, and liposomes and methods of thereof.

Concise synthesis of hydroxy β -methyl fatty acid ethyl esters

Hydroxy β-methyl fatty acid ethyl esters bearing different carbon chain lengths and varying hydroxyl group positions were successfully synthesized from symmetric diols. These fatty acid derivatives are useful intermediates of chemical probes for metabolic

Concise synthesis of hydroxy β-methyl fatty acid ethyl esters

Hydroxy β-methyl fatty acid ethyl esters bearing different carbon chain lengths and varying hydroxyl group positions were successfully synthesized from symmetric diols. These fatty acid derivatives are useful intermediates of chemical probes for metabolic

Cyclohexane Rings Reduce Membrane Permeability to Small Ions in Archaea-Inspired Tetraether Lipids

Extremophile archaeal organisms overcome problems of membrane permeability by producing lipids with structural elements that putatively improve membrane integrity compared to lipids from other life forms. Herein, we describe a series of lipids that mimic some key structural features of archaeal lipids, such as: 1) single tethering of lipid tails to create fully transmembrane tetraether lipids and 2) the incorporation of small rings into these tethered segments. We found that membranes formed from pure tetraether lipids leaked small ions at a rate that was about two orders of magnitude slower than common bilayer-forming lipids. Incorporation of cyclopentane rings into the tetraether lipids did not affect membrane leakage, whereas a cyclohexane ring reduced leakage by an additional 40 %. These results show that mimicking certain structural features of natural archaeal lipids results in improved membrane integrity, which may help overcome limitations of many current lipid-based technologies.

Evaluation of the effect of fluorination on the property of monofluorinated dimyristoylphosphatidylcholines

The synthesis of three monofluorinated dimyristoylphosphatidylcholines (F-DMPC's), with the fluorine atom located at the extremities of the acyl chain in position 2 of the glycerol (sn-2), is described. The synthetic strategy relies on the coupling of 1-myristoyl-2-hydroxy-sn-glycero-3-phosphocholine (14:0 lyso-PC) and three different fluorinated fatty acids. FTIR results suggest that the presence of the fluorine atom does not significantly perturb the lipid phase transition temperature and conformational order even though a small increase in the phase transition temperature is observed for the 14F derivative. Overall, comparison with previously reported F-DMPC's where the fluorine atom is located in the middle or close from either side supports the fact that monofluorination of the acyl chain in sn-2 brings minimal perturbation to the lipid bilayer. F-DMPC's could therefore potentially be used as NMR probes for the investigation at the molecular level of the interaction between drugs or peptides and lipid membranes and for the study of membrane topology.

Stereochemistry of sagittamide A: Prediction and confirmation

The C5-C10 relative stereochemistry of sagittamide A was predicted, with the use of the 3JH,H profiles assembled from the spin-coupling constants reported in the literature. The predicted relative stereochemistry was then confirmed by a total synthesis of two relevant remote diastereomers. The absolute configuration of sagittamide A was established through a detailed 1H NMR analysis of the two remote diastereomers, followed by doping experiments of them with the authentic natural product.

Products of cytochrome P450Biol (CYP107H1)-catalyzed oxidation of fatty acids

(Matrix presented) Oxidation of tetradecanoic and hexadecanoic acids by cytochrome P450Biol (CYP107H1) produces mainly the 11-, 12-, and 13-hydroxy C14 fatty acids and the 11- to 15-hydroxy C16 fatty acids, respectively. In contrast to previous reports, terminal hydroxylation is not observed. The enantiospecificity of fatty acid hydroxylation by P450Biol was also determined, and the enzyme was shown to be moderately selective for production of the (R)-alcohols.

Detection of 2-substituted cyclobutanones as irradiation products of lipid-containing foods: Synthesis and applications of cis- and trans-2-(tetradec-5′-enyl)cyclobutanones and 11-(2′-oxocyclobutyl)-undecanoic acid

cis- (3cis) and trans-2-(tetradec-5′-enyl)cyclobutanone (3trans) have been chemically synthesised and used in the unambiguous identification of the cis isomer 3cis in irradiated meat (example chicken) and fruit (example pa