The Stereochemistry of the Perbenzoic Acid Oxidation of Optically Active exo-Acetylnorbornane1

1959 ◽  
Vol 81 (15) ◽  
pp. 4088-4094 ◽  
Author(s):  
Jerome A. Berson ◽  
Shigeto Suzuki
1947 ◽  
Vol 69 (11) ◽  
pp. 2899-2901 ◽  
Author(s):  
Lewis Hastings Sarett

1953 ◽  
Vol 31 (4) ◽  
pp. 396-417 ◽  
Author(s):  
R. U. Lemieux

Methanolysis of ustilagic acid and hydrolysis of the methyl esters formed yielded a crystalline acidic fraction which was essentially a mixture of two substances termed the ustilic acids A and B. The acids were separated as their iso-propylidene derivatives. The ustilic acids cocrystallize to mixtures with melting points intermediate between those of the pure compounds. Conversion of ustilic acid A, m.p. 112–113 °C, [α]D −8° in methanol, which made up about 70% of the mixture, by hydrogenolysis to palmitic acid, by oxidation with chromic oxide to pentadecanedioic acid, and by lead tetraacetate oxidation followed by hydrogenation to 15-hydroxypentadecanoic acid showed the substance to be an optically active form of 15,16-dihydroxyhexadecanoic acid. Conversion of ustilic acid B, m.p. 140–141 °C, [α]D−10° in methanol, by sodium bismuthate oxidation followed by hydrogenation to 1,14-dihydroxytetradecane, by chromic acid oxidation of its methyl ester followed by hydrolysis of the product, and peroxide oxidation of the α-keto acid thus formed to tetradecanedioic acid, and by hydrogenolysis of the C2-carbon atom through a series of reactions to ustilic acid A, showed the substance to be an optically active form of 2,15,16-trihydroxy-hexadecanoic acid. Optically active forms of 2,15-dihydroxypentadecanoic and 2-hydroxypentadecanoic acids were prepared from ustilic acid B. Application of certain empirical rules of rotation to derivatives of these 2-hydroxyacids showed them to possess the D-configuration. Reduction of ustilic acid B with lithium aluminum hydride gave meso-1,2,15,16-tetrahydroxyhexadecane. Thus, ustilic acid B was the 2D,15D,16-trihydroxyhexadecanoic acid and the ustilic acid A was the 15D,16-dihydroxyhexadecanoic acid. Several derivatives of the above described acids were prepared.


ChemInform ◽  
1988 ◽  
Vol 19 (33) ◽  
Author(s):  
M. S. AHMAD ◽  
M. MUSHFIQ ◽  
K. SALEEM ◽  
Z. ALAM ◽  
N. IQBAL

1954 ◽  
Vol 76 (8) ◽  
pp. 2265-2266 ◽  
Author(s):  
Norma S. Leeds ◽  
David K. Fukushima ◽  
T. F. Gallacher

1986 ◽  
Vol 17 (44) ◽  
Author(s):  
SHAFIULLAH SHAFIULLAH ◽  
I. H. SIDDIQUI ◽  
S. HUSAIN

1950 ◽  
Vol 72 (2) ◽  
pp. 882-885 ◽  
Author(s):  
T. F. Gallagher ◽  
Theodore H. Kritchevsky

Author(s):  
Catherine A. Taylor ◽  
Bruce M. Jarnot

Peroxisome induction can be expressed as an increase in peroxisome area (proliferation) or as an increase in peroxisomal fatty acid oxidation (activity). This study compares proliferation and activity as endpoints for hepatic peroxisome induction by perfluorodecanoic acid (PFDA). Fluorocarboxylic acids such as PFDA represent a class of compounds possessing commercially important surfactant properties. A single 50 mg/Kg ip. dose of PFDA produces a characteristic “wasting syndrome” in male F-344 rats. Symptoms include hypophagia, weight loss, hepatomegaly, and delayed lethality. Hepatic studies reveal changes similar to those seen with the hypolipidemic agent clofibrate. These include mitochondrial disruption, endoplasmic reticulum and peroxisome proliferation, and increased peroxisomal acyl-CoA oxidase activity.Male Fisher-344 rats received a single ip. dose of 2, 20, or 50mg/Kg PFDA dissolved in 1:1 propylene glycol/water and were sacrificed 8 days post-dose. All control rats received an equal volume of vehicle ip. Animals were provided food and water ad libitum, except pair-fed controls which received the same restrictive food intake consumed by their weight-paired dosed partners (50mg/Kg PFDA group) to simulate the hypophagia associated with PFDA.


TAPPI Journal ◽  
2012 ◽  
Vol 11 (8) ◽  
pp. 51-58
Author(s):  
ANTTI HAAPALA ◽  
MIKA KÖRKKÖ ◽  
ELISA KOIVURANTA ◽  
JOUKO NIINIMÄKI

Analysis methods developed specifically to determine the presence of ink and other optically active components in paper machine white waters or other process effluents are not available. It is generally more interest¬ing to quantify the effect of circulation water contaminants on end products. This study compares optical techniques to quantify the dirt in process water by two methods for test media preparation and measurement: direct process water filtration on a membrane foil and low-grammage sheet formation. The results show that ink content values obtained from various analyses cannot be directly compared because of fundamental issues involving test media preparation and the varied methodologies used to formulate the results, which may be based on different sets of assumptions. The use of brightness, luminosity, and reflectance and the role of scattering measurements as a part of ink content analysis are discussed, along with fine materials retention and measurement media selection. The study concludes with practical tips for case-dependent measurement methodology selection.


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