Literature DB >> 20161109

The first total synthesis of (±)-4-methoxydecanoic acid: a novel antifungal fatty acid.

Néstor M Carballeira1, Carlos Miranda, Keykavous Parang.   

Abstract

The hitherto unknown (±)-4-methoxydecanoic acid was synthesized in six steps and in 25% overall yield starting from commercially available 4-penten-1-ol. The title compound demonstrated seventeen fold higher antifungal activity (MIC = 1.5 mM) against Candida albicans ATCC 60193 and Cryptococcus. neoformans ATCC 66031 when compared to unsubstituted n-decanoic acid. Our results demonstrate that Mid-chain methoxylation appears to be a viable strategy for increasing the fungitoxicity of fatty acids.

Entities:  

Year:  2009        PMID： 20161109      PMCID： PMC2739663          DOI： 10.1016/j.tetlet.2009.07.074

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

Review 1.  Evaluation of the potential effects of ingredients added to cigarettes. Part 1: cigarette design, testing approach, and review of results.

Authors:  E L Carmines
Journal:  Food Chem Toxicol       Date:  2002-01       Impact factor: 6.023

2.  In vitro killing of Candida albicans by fatty acids and monoglycerides.

Authors:  G Bergsson; J Arnfinnsson; H Thormar
Journal:  Antimicrob Agents Chemother       Date:  2001-11       Impact factor: 5.191

3.  Production, Identification, and Toxicity of (gamma)-Decalactone and 4-Hydroxydecanoic Acid from Sporidiobolus spp.

Authors:  G Feron; L Dufosse; E Pierard; P Bonnarme; J L Quere; H Spinnler
Journal:  Appl Environ Microbiol       Date:  1996-08       Impact factor: 4.792

4.  Antifungal 3-hydroxy fatty acids from Lactobacillus plantarum MiLAB 14.

Authors:  Jörgen Sjögren; Jesper Magnusson; Anders Broberg; Johan Schnürer; Lennart Kenne
Journal:  Appl Environ Microbiol       Date:  2003-12       Impact factor: 4.792

5.  Synthesis and antifungal properties of alpha-methoxy and alpha-hydroxyl substituted 4-thiatetradecanoic acids.

Authors:  Néstor M Carballeira; Rosann O'Neill; Keykavous Parang
Journal:  Chem Phys Lipids       Date:  2007-06-28       Impact factor: 3.329

6.  Effect of cold storage and packaging material on the major aroma components of sweet cream butter.

Authors:  Patricio R Lozano; Evan R Miracle; Andrea J Krause; Maryanne Drake; Keith R Cadwallader
Journal:  J Agric Food Chem       Date:  2007-08-17       Impact factor: 5.279

7.  Characterization of the key aroma compounds in apricots (Prunus armeniaca) by application of the molecular sensory science concept.

Authors:  Veronika Greger; Peter Schieberle
Journal:  J Agric Food Chem       Date:  2007-05-27       Impact factor: 5.279

8.  Total synthesis and in vitro-antifungal activity of (+/-)-2-methoxytetradecanoic Acid.

Authors:  Néstor M Carballeira; Denisse Ortiz; Keykavous Parang; Soroush Sardari
Journal:  Arch Pharm (Weinheim)       Date:  2004-03       Impact factor: 3.751
  8 in total
  2 in total

1.  2-Methoxylated FA Display Unusual Antibacterial Activity Towards Clinical Isolates of Methicillin-Resistant Staphylococcus aureus (CIMRSA) and Escherichia coli.

Authors:  Néstor M Carballeira; Nashbly Montano; Christian Morales; Joseph Mooney; Xiomara Torres; Dakeishla Díaz; David J Sanabria-Rios
Journal:  Lipids       Date:  2017-05-18       Impact factor: 1.880

2.  Development of a Non-Aqueous Dispersion to Improve Intestinal Epithelial Flux of Poorly Permeable Macromolecules.

Authors:  Sam Maher; Mekki Medani; Nestor N Carballeira; Desmond C Winter; Alan W Baird; David J Brayden
Journal:  AAPS J       Date:  2016-10-13       Impact factor: 4.009
  2 in total

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