Monday, April 25, 2011

Seminar Critique

The topic of discussion for the seminar was Tobacco smoking during pregnancy and Biomarkers of exposure and relationship to genetics. The speaker was Steven R. Myers, Ph. D, an associate professor of the Department of Pharmacology and Toxicology at the University of Louisville, School of Medicine. He talked about the different chemicals found in cigarette and how these chemicals can be traced to see if they affected the mother and the baby by the use of biomarkers.

A biomarker is a molecular, biochemical, or cellular alterations that are measurable in biological media, such as human tissues, cells, or fluids. For a biomarker to be useful as a monitoring tool, the following criteria has to be met which are specificity, sensitivity and practicality. Biomarkers are needed because there are 4000 chemicals that are generated during burning and smoking of tobacco. These chemicals are the leading cause of avoidable cancer deaths in the US and the world.

To monitor the effect of smoking during pregnancy, amniotic fluid was used as a biomarker during the first trimester of pregnancy and hemoglobin as a biomarker of carcinogen and tobacco exposure.

From the research they further proved that if an expectant mother smokes during her pregnancy, certain risk factors are increased. These factors include:
- miscarriages
- stillborn babies
- premature birth
- low birth-weight babies
- placenta previa
- placental abruption
- Sudden Infant Death Syndrome (SIDS)
Because of these complications many babies are born with low IQ levels by 25-30% and with learning difficulties as a child. A reported 2,000,000 ear infections and 530,000 doctor visits for asthma are reported on a yearly basis.

People who consume tobacco may develop illnesses such as:
- cancer
- cardiovascular disease
- cerebrovascular diseases
- respiratory diseases and
- pediatric diseases.

 One of the compounds found in cigarette smoke is 4-aminobiphenol which has the structure shown below.



Wednesday, April 20, 2011

Hell-Volhard Zelinsky Halogenation

The Hell-Volhard Zelinsky reaction is a halogenation reaction at the alpha carbon of a carboxylic acid. The reaction is initiated by a catalytic amount of PBr3, after which one molar equivalent of Br2 is added. The carboxylic OH is replaced by the Br resulting in a carboxylic acid bromide. The acyl bromide then tautomerizes to the enol so it can brominate again at the alpha carbon. The general mechanism of the reaction is shown below:

A reaction that employs the use of the Hell-Volhard Zelinsky mechanism is the synthesis of Dimethylketene. Its IUPAC name is 2-methyl-1-propen-1-one and it has a molecular formula of C4H6O. Its structure is shown below:
The physical properties of dimethylketene are:
- molecular weight: 70.09g/mol
- boiling point: 34*C
- density: 0.775g/cm^3

The reaction scheme for the synthesis of this compound from its starting material is shown below:


The starting material is 2-methylpropanoic acid which is catalyzed by the PBr3 resulting in the substitution of the carboxylic OH by a Br and an addition of Br at the alpha carbon. The second step in the procedure is a different kind of reaction that results in the final product dimethylketene. The true product of the Hell-Volhard Zelinsky reaction is the 1,2-dibromo-2-methylpropanone. This compound has a molecular weight of 230.09g/mol.

As of to the physical properties of the compound, I could not find any information.

References:
http://www.qwiki.com/q/#!/Hell-Volhard-Zelinsky_halogenation
http://www.chemspider.com/Chemical-Structure.120167.html

Saturday, April 9, 2011

e-caprolactone

ε-Caprolactone (epsilon-caprolactone) is a cyclic ester, a member of the lactone family, with a seven-membered ring with the formula (CH2)5CO2 and IUPAC name of 2-oxepanone. It is a colorless, miscible liquid with most organic solvents and it is produced on a very large scale as a precursor to caprolactam
The physical properties of caprolactone are as follows:
- molecular weight: 114.14g/mole
- melting pt.: -1*C
- boiling pt.: 253*C
- density: 1.030g/cm^3
- solubility: > 1000mg/L (20*C)

Caprolactone is often used as a precursor to caprolactam. It is also a monomer used in the manufacture of highly specialized polymers. An example of a polymer is polyglecaprone, used as suture material in surgery. Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid.

The dominant reaction of caprolactone which is the conversion to caprolactam, involves treatment with hydroxylamine followed by sulfuric acid to give the desired lactam as shown below in a multi-step synthesis.