Synthesis of a Broad Array of Highly Functionalized, Enantiomerically Pure Cyclohexanecarboxylic Acid Derivatives by Microbial Dihydroxylation of Benzoic Acid and Subsequent Oxidative and Rearrangement Reactions

2001 ◽  
Vol 3 (18) ◽  
pp. 2923-2926 ◽  
Author(s):  
Andrew G. Myers ◽  
Dionicio R. Siegel ◽  
Daniel J. Buzard ◽  
Mark G. Charest
Keyword(s):  
Benzoic Acid ◽  
Enantiomerically Pure ◽  
Cyclohexanecarboxylic Acid ◽  
Broad Array ◽  
Rearrangement Reactions

The metabolism of cyclohexanecarboxylic acid and 3-cyclohexenecarboxylic acid by Pseudomonas putida

1982 ◽  
Vol 28 (12) ◽  
pp. 1324-1329 ◽  
Author(s):  
E. R. Blakley ◽  
B. Papish
Keyword(s):  
Benzoic Acid ◽  
Pseudomonas Putida ◽  
Sole Source ◽  
Oxidation Pathway ◽  
Cyclohexanecarboxylic Acid

A strain of Pseudomonas putida grew rapidly on cyclohexanecarboxylic acid as a sole source of carbon. A CoA-mediated β-oxidation pathway was induced for the metabolism of the compound. The organism could not utilize 3-cyclohexenecarboxylic acid as a sole source of carbon for growth, but cells grown on gluconate in the presence of 3-cyclohexenecarboxylic acid were induced to metabolize cyclohexanecarboxylic acid, benzoic acid, and catechol. Evidence is presented that 3-cyclohexenecarboxylic acid was slowly metabolized by a β-oxidation pathway and by a pathway involving benzoic acid as an intermediate. For this strain of Pseudomonas putida, 3-cyclohexenecarboxylic acid acts as an oxidizable, nongrowth substrate and induces the metabolism of cyclohexanecarboxylic acid and benzoic acid.

Significant effect of base on the improvement of selectivity in the hydrogenation of benzoic acid over NiZrB amorphous alloy supported on γ-Al2O3

2015 ◽  
Vol 5 (6) ◽  
pp. 3281-3287 ◽  
Author(s):  
Xin Wen ◽  
Yingying Cao ◽  
Xianliang Qiao ◽  
Libo Niu ◽  
Li Huo ◽  
...  
Keyword(s):  
Amorphous Alloy ◽  
Benzoic Acid ◽  
Cyclohexanecarboxylic Acid

The selectivity for cyclohexanecarboxylic acid was significantly enhanced by adding small amounts of bases in benzoic acid hydrogenation.

scholarly journals Biodegradation ofn-Alkylcycloalkanes and n-Alkylbenzenes via New Pathways in Alcanivorax sp. Strain MBIC 4326

2001 ◽  
Vol 67 (4) ◽  
pp. 1970-1974 ◽  
Author(s):  
Tapan K. Dutta ◽  
Shigeaki Harayama
Keyword(s):  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Side Chain ◽  
Alkyl Side Chain ◽  
Cyclohexanecarboxylic Acid ◽  
Long Chain

ABSTRACT The degradation of long-chain n-alkylbenzenes andn-alkylcyclohexanes by Alcanivorax sp. strain MBIC 4326 was investigated. The alkyl side chain of these compounds was mainly processed by β-oxidation. In the degradation ofn-alkylcyclohexanes, cyclohexanecarboxylic acid was formed as an intermediate. This compound was further transformed to benzoic acid via 1-cyclohexene-1-carboxylic acid.

Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols

2011 ◽  
Vol 76 (20) ◽  
pp. 8537-8542 ◽  
Author(s):  
J. Adam McCubbin ◽  
Samantha Voth ◽  
Oleg V. Krokhin
Keyword(s):  
Benzoic Acid ◽  
Allylic Alcohols ◽  
Acid Catalysts ◽  
Rearrangement Reactions

scholarly journals The origin of urinary aromatic compounds excreted by ruminants 1. The metabolism of quinic, cyclohexanecarboxylic and non-phenolic aromatic acids to benzoic acid

1982 ◽  
Vol 47 (1) ◽  
pp. 139-154 ◽  
Author(s):  
A. K. Martin
Keyword(s):  
Benzoic Acid ◽  
Cinnamic Acid ◽  
Phenylacetic Acid ◽  
Rumen Fluid ◽  
Acid Output ◽  
The Body ◽  
Urinary Output ◽  
Aromatic Acids ◽  
Phenylpropionic Acid ◽  
Cyclohexanecarboxylic Acid

1. The contribution of dietary constituents to the large urinary output of benzoic acid characteristic of ruminants and some herbivores is not well understood.2. Methods for the analysis of quinic, cyclohexanecarboxylic, benzoic, phenylacetic, 3-phenylpropionic and cinnamic acids in urine and in rumen fluids were developed.3. The urinary output of aromatic acids by sheep given seven rations was determined: benzoic acid output varied between 2·8 and 7·8 g/d; phenylacetic acid output between 0·16 and 1·3 g/d; cinnamic acid between 0·08 and 0·25 g/d and small amounts of 3-phenylpropionic acid were found in some samples.4. Increments in urinary aromatic acid excretion were determined when the acids listed in paragraph 2 were infused via rumen or abomasal cannulas.5. When cyclohexanecarboxylic acid was infused 40% of the dose was excreted as urinary benzoic acid after either route of infusion. Quinic acid was completely metabolized in the rumen: following rumen infusion between 16 and 53% of the infused acid was recovered as urinary benzoic acid; none was so recovered after abomasal infusion.6. Urinary recoveries of rumen- and abomasally-infused aromatic acids were: benzoic acid 90 and 88% respectively as benzoic acid, phenylacetic acid 78 and 83% respectively as phenylacetic acid, 3-phenylpropionic acid 96 and 105% respectively as benzoic acid and cinnamic acid, 70 and 70% respectively as benzoic acid.7. The concentration of aromatic acids in rumen fluid varied with time after feeding: cyclohexanecarboxylic acid was maximal (7 mg/l) 1 h after feeding, benzoic acid was always a minor component (0·5 ± 0·5 mg/l), phenylacetic acid varied between 0 and 35 mg/1 and 3-phenylpropionic acid between 25 and 47 mg/l. Cinnamic acid was not found in rumen fluid but on rumen infusion of this acid the concentration of 3-phenylpropionic acid in rumen fluid increased by 10 mg/l rumen fluid per g infused per d.8. The incomplete metabolism of quinic and cyclohexanecarboxylic acids to urinary benzoic acid is discussed. It is concluded that the principal dietary precursors of urinary benzoic acid in ruminants are compounds yielding 3-phenylpropionic acid on microbial fermentation in the rumen. The small amount of cinnamic acid characteristic of ruminant urine arises as an intermediate in the β-oxidation of 3-phenylpropionic acid in the body tissues.

Corynebacterium cyclohexanicum n. sp.: a cyclohexanecarboxylic acid utilizing bacterium

1973 ◽  
Vol 19 (8) ◽  
pp. 937-942 ◽  
Author(s):  
Tai Tokuyama ◽  
Toshi Kaneda
Keyword(s):  
Benzoic Acid ◽  
Yeast Extract ◽  
Gram Positive ◽  
Separate Species ◽  
Biochemical Characteristics ◽  
Cyclohexanecarboxylic Acid ◽  
Bacterium Strain

A cyclohexanecarboxylic acid utilizing bacterium, strain MU, has been isolated from soil and its taxonomic and physiological nature studied. The organism requires biotin or an unidentified factor present in yeast extract for growth, and can use one of various acids, alcohols, and carbohydrates as the sole carbon source.As the organism is a non-motile rod, gram-positive, non-sporing, not acid-fast, catalase-positive, and aerobic, it is identified as a Corynebacterium. Various growth and biochemical characteristics show that the organism is closely related to Corynebacterium equi but differs in several characteristics. Hence, a separate species, Corynebacterium cyclohexanicum is proposed for strain MU because of its unique use of cyclohexanecarboxylic acid. Results from manometric experiments indicate that its metabolism of cyclohexanecarboxylic acid is closely related to the well-established metabolic scheme of benzoic acid.

ChemInform Abstract: Mild and Tunable Benzoic Acid Catalysts for Rearrangement Reactions of Allylic Alcohols.

ChemInform ◽  
2012 ◽  
Vol 43 (8) ◽  
pp. no-no
Author(s):  
J. Adam McCubbin ◽  
Samantha Voth ◽  
Oleg V. Krokhin
Keyword(s):  
Benzoic Acid ◽  
Allylic Alcohols ◽  
Acid Catalysts ◽  
Rearrangement Reactions

TEM characterization of proton-exchanged LiNbO3 optical waveguides

1986 ◽  
Vol 44 ◽  
pp. 480-481
Author(s):  
W. E. Lee
Keyword(s):  
Refractive Index ◽  
Benzoic Acid ◽  
Optical Waveguides ◽  
Total Internal Reflection ◽  
Index Of Refraction ◽  
Optical Measurements ◽  
Lithium Ions ◽  
Wide Channel ◽  
Tem Characterization

An optical waveguide consists of a several-micron wide channel with a slightly different index of refraction than the host substrate; light can be trapped in the channel by total internal reflection.Optical waveguides can be formed from single-crystal LiNbO3 using the proton exhange technique. In this technique, polished specimens are masked with polycrystal1ine chromium in such a way as to leave 3-13 μm wide channels. These are held in benzoic acid at 249°C for 5 minutes allowing protons to exchange for lithium ions within the channels causing an increase in the refractive index of the channel and creating the waveguide. Unfortunately, optical measurements often reveal a loss in waveguiding ability up to several weeks after exchange.

Maintaining Your CCCs: It’s Simple and Offers a Broad Array of Options

ASHA Leader ◽  
2006 ◽  
Vol 11 (10) ◽  
pp. 18-30
Author(s):  
Craig E Coleman ◽  
Carol Williams
Keyword(s):  
Broad Array
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