Woodward cis-Hydroxylation Reaction

Chemistry, Medicine
Silver acetate, in combination with iodine, forms the initial reactant package for the Woodward reaction. This reaction, carried to completion, selectively converts an alkene into a cis-diol. The prefix cis- refers to the addition of two atoms (or groups of atoms) to the same side of a molecular double bond. Trans-, when used, refers to addition across the double bond – of one atom or group to one side, one to the other side. The Mechanism The mechanism is illustrated in the image (below) up to the point of hydrolysis. The product of that hydrolysis is pictured in the introductory image. We see, first, the iodine splits, the I atom adding to the double bond. In the next part of the reaction, the silver atom attaches to the iodine, and…
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Cutting Edge Technology: Gold Nanoparticles for Research

Chemistry, Medicine
[caption id="attachment_24005" align="alignright" width="480"] Using a nanoparticle-based sensing strategy for determining protein levels in blood. Image by Vincent Rotello, University of Massachusetts[/caption] There is spellbinding beauty in “yellow, yellow” gold. But gold is not always yellow. If individual gold atoms are clumped together in small quantities – agglomerated – they assume various colors depending upon the physical properties of the agglomerates. If all the particles are of about the same size and shape, the color and other physical properties, when duplicated, are exactly reproduced. Interestingly, aggregates can be grown with a specific geometry. They can even be grown into the particularly useful form – nanorods. The assortment of colors that can be produced ranges from red to purple to blue. But there is a problem. If gold nanoparticles grown with…
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Hydrochlorothiazide HCTZ: The Time-Tested, Inexpensive B.P. Medication

Chemistry, Medicine
Many think that “New is better.” In technology, such thinking often proves true. But is it always the case? No. Consider pharmacology. New drugs promise improved health, a better quality of life. Yet negative side effects, some not having had sufficient time to surface, may discourage a medication’s use, perhaps even warranting its removal from pharmacy shelves. In the United States, one of the most common health issues is hypertension – high blood pressure. So it’s no surprise many medicines have been formulated to fight this condition. Although many new drugs are now available, hydrochlorothiazide (HCTZ) remains a “first choice” for the treatment of hypertension.¹ Why so? Few medicines have such a generally excellent track record. HCTZ (or for short, HCT) has few side-effects.² Hydrochlorothiazide is inexpensive; perhaps it is…
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Giant Hogweed: The Truly Horrible Plant with Redeeming Qualities?

Health, Medicine
[caption id="attachment_23846" align="alignright" width="480"] Attractive, after a fashion, the Giant Hogweed. Image MabelAmber[/caption] The Giant Hogweed is a hot topic in the United Kingdom, and now also in the United States. Have you personally “experienced” the Giant Hogweed, Heracleum mantegazzianum? We’re not speaking of Heracleum sphondylium, the Common Hogweed, no. Giant Hogweed has a horrific reputation, and is widely considered a noxious weed. Its reputation has taken it from the hospital and the laboratory to detective TV. For instance, Giant Hogweed is the weapon of choice in the Rosemary & Thyme pilot episode entitled, “And No Birds Sing.” Giant Hogweed Toxins The chemicals in Giant Hogweed that provide its sordid reputation are furanocoumarins – or (for short) furocoumarins. This name is derived from the characteristic two ring portions they share…
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Blood Sucking Bed Bug: A Vector of Disease?

Health, Medicine
[caption id="attachment_23698" align="alignright" width="480"] Bedbug mouthparts - Image by Janice Haney Carr, courtesy of the U.S. Centers for Disease Control and Prevention[/caption] Everyone hates the buzzing mosquito. Then too, people fuss when they find a tick burrowed in their skin. What about itching? Chiggers are the King of Itch. Worse, however, than any of the aforementioned is an infestation of Cimex lectularius, the bed bug most common to North America. This blood-sucking varmint is very difficult to control and even harder to eradicate. Pests as Vectors of Disease Beyond being simply annoying, some blood-feeding insects can pose serious human health risks. So how do these four pests compare when it comes to transmitting disease-causing organisms? Both mosquitoes and ticks are legendary vectors for disease. Mosquitoes, for example, spread some serious,…
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Tylenol, Its Structure, Nomenclature, and a Lab Synthesis

Chemistry, Medicine
Tylenol® is a trade name for acetaminophen.¹ Does the latter word sound foreign to you? Let's find out what it means. This compound contraction combines acetyl with amino with phenol. What's in a Name? Does acetyl remind you of acetic acid or vinegar? Acetic acid is CH₃COOH. The acetyl group is written CH₃CO–. Amino is familiar too, as in amino acid? The basic amino group is written NH₂–, though at times one or both of the hydrogen atoms are replaced by something else, as it is for Tylenol. Finally, "phen" stands for phenyl. Remove one atom from a benzene ring and you have phenyl. C₆H₅– is the simplest phenyl ring. Again, hydrogen atoms may be replaced with something else. The end result of putting these together to form acetaminophen is…
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Slip ’em a Mickey: Chloral Hydrate, a Stabilized Geminal Diol

Health, Medicine
Among the endless thousands of organic compounds that are familiar to the public, one is associated with foul bars, booze, and foul play. It is chloral hydrate (Cl₃C-CH(OH)₂). Combined with an alcoholic beverage, the result, an infamous "Mickey Finn" causes the victim to pass out as quickly as if he had been knocked out. Mickey (Not Steamboat Mickey) In the Movies In old-movie and TV shows, the bad guy (often in a saloon) wants to capture his victim by rendering him unconscious. Maybe he even wants to sell the man to a ship's captain who needs to complete his crew. The poor guy is Shanghaied! An interesting example is this old Bonanza western TV show episode: Was There an Actual Mickey Finn? It appears there was! In the latter part…
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The Deadly Morning Sickness Medication Thalidomide – Still In Use Today?

Medicine, People
Available to the general public in 1957, thalidomide¹ was initially prescribed as a sedative or hypnotic medication. A sedative, we know, is intended to "calm the nerves". What is an hypnotic? A number of online definitions suggest an hypnotic is a drug, likened to hypnotism, tending to produce sleep. A little later, it was given to fight nausea, and was prescribed to expectant mothers who experienced morning sickness. Who knew the morning sickness medication thalidomide would cause devastation to the babies? Search the web by entering the word thalidomide, and choosing the category images, and you will see quite a few photos of former "thalidomiders". A full-term pregnancy lasts nine months. While expectant mothers may have been calmed and their nausea lessened, it didn't take long for thalidomide to produce…
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Dangerous Medicine Including Foot Fluoroscope (X-ray) Machines

History, Medicine
[caption id="attachment_19620" align="alignright" width="440"] Operator / observer side Adrian Special fluoroscope[/caption] Medicine has always sought to cure sufferers of what ails them. In the physician's valiant efforts, sometimes, not only success failed to be achieved, but the sufferer was worse off. In the Bible book bearing his name, Mark relates one well-known ancient example: "Now there was a woman subject to a flow of blood twelve years, and she had been put to many pains by many physicians and had spent all her resources and had not been benefited but, rather, had got worse." -Mark 5:25, 26. Again, mercury and other hazardous substances were sometimes used in the formulation of medications. In fact, the body of one famous individual with a violent disposition was exhumed to determine if there was…
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Should You Use Ordinary Soap or Antibacterial Soap?

Health, Medicine
[caption id="attachment_19376" align="alignright" width="480"] Triclosan - spacefill model.[/caption] In the last few decades, personal cleanliness has been promoted intensely. One of the most recent marketable personal hygiene items is hand sanitizer. People purchase and use the scented stuff in all manner of situations, but especially after they shake hands with someone they suspect is sick! A typical sanitizer composition contains alcohol, a thickening agent, and scent. Another popular hygiene product is antibacterial soap. This is so despite the widespread successful use of regular soap. People want the latest and greatest. Newer must be better, right? Yet antibacterial soaps have not been received altogether with open arms. Antibacterial Soaps - Controversy, Big Time The concept of an antimicrobial or antibacterial soap seems commendable. Yet, reality does not always measure up to…
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