Food Lipids: Chemistry, Nutrition, and Biotechnology

Food Lipids: Chemistry, Nutrition, and Biotechnology

Organocatalytic 1,3-dipolar cycloaddition reactions of ketones and azides with water as a solvent

 

Green Chem., 2013, 15,2384-2388
DOI: 10.1039/C3GC41126E, Communication
*
Corresponding authors
a
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore
E-mail: chmwangj@nus.edu.sg ;
Fax: (+)65-6516-1691
b
HuBei Collaborative Innovation Center of Non-power Nuclear Technology, Hubei University of Science and Technology, Hubei Province, China

Received 12 Jun 2013, Accepted 19 Jul 2013
First published online 22 Jul 2013

We reported an enamine catalyzed strategy to fully promote a 1,3-dipolar cycloaddition to access a vast pool of substituted 1,2,3-triazoles in water.

Porous Organic Polymer Captures CO2

 

 

 

 

 

A moisture-stable porous organic polymer containing carboxy and triazole groups reversibly and selectively captures carbon dioxide

Read more

A flexible Pinner preparation of orthoesters: the model case of trimethylorthobenzoate

 

 

Dipartimento di Scienze Molecolari e Nanosistemi dell’Universita Ca’ Foscari Venezia, Centre for Sustainable Technologies, calle Larga S. Marta, 2137-30123 Venezia, Italy 
E-mail: marco.noe@unive.it

Green Chem., 2013,15, 2252-2260

DOI: 10.1039/C3GC40774H
Received 24 Apr 2013, Accepted 10 Jun 2013

 
The Pinner preparation of orthoesters was revisited achieving remarkable improvements. Outstandingly an unprecedented synthesis of trimethylorthobenzoate starting from benzonitrile has been described.
In the absence of additional solvents,
a novel procedure was implemented for the synthesis oftrimethylorthoesters through the Pinner reaction. At 5 °C, the reaction of both aliphatic and aromatic nitriles (RCN; R = Et, Bu, Ph) with a moderate excess of MeOH and gaseous HCl gave the corresponding imidate hydrochlorides [RC([double bond, length as m-dash]NH)OR′·HCl]
 
in excellent yields (>90%). At 25–65 °C, the methanolysis of alkyl imidate salts provided trimethylortho-propionate and valerate, while only traces of trimethylorthobenzoate (TMOB) were observed. However, the aromatic hydrochloride could be readily converted into the hydrogenphosphate salt [PhC([double bond, length as m-dash]NH)OR′·H3PO4] which, in turn, underwent a selective (>80%) reaction with MeOH to produce TMOB in a 62% isolated yield. This allowed for an unprecedented Pinner-type synthesis of TMOB starting from benzonitrile, rather than from the highly toxic trichloromethylbenzene. Overall, remarkable improvements in safety and process intensification were achieved.
 
 

Large-ring lactones from plant oils

 

Timo Witta and   Stefan Mecking*a  
Chair of Chemical Materials Science, University of Konstanz, Department of Chemistry, Universitätsstraße 10, 78457 Konstanz, Germany 
E-mail: stefan.mecking@uni-konstanz.de ;
Fax: +49 7531 885152 ;
Tel: +49 7531 882593
 
Green Chem., 2013, Advance Article

DOI: 10.1039/C3GC40905H
Received 15 May 2013, Accepted 11 Jul 2013
First published online 29 Jul 2013
A synthesis route for macrocyclic compounds such as lactones starting from common plant oils has been developed.
Large-ring lactones from plant oils

 
 
Large-ring lactones and lactams were prepared utilising the full fatty acid chain of common plant oils as a source of the macrocycle. Ring closure via acyloin condensation does not require large volumes of solvents for dilution. Nonadecalactone (NDL) and tricosalactone (TCL) can be converted to novel polyesters by ring opening.

Watermelon Juice Prevents Aching Muscles Food Chemistry: The amino acid L-citrulline found in the fruit could help athletes avoid muscle soreness after a hard workout

Photo of watermelon juice smoothie in tall glass

The Next Sports Drink?
Watermelon drinks, like this smoothie, could help cut down on muscle soreness after intense exercise.
Credit: Shutterstock
Before taking a long bike ride on a hot summer day, have some watermelon: The juicy fruit may ward off muscle pains. Researchers report that people who drank watermelon juice before exercising felt less sore the next day than those who drank a pink placebo beverage (J. Agric. Food Chem. 2013, DOI: 10.1021/jf400964r). They also found that cells absorb the presumed active ingredient, L-citrulline, more readily from unpasteurized watermelon juice than from plain water spiked with the compound, suggesting the natural source is the optimal delivery
medium.