Coby
moleculeoftheday
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Vinpotecine is a derivative from a compound found in the lesser periwinkle plant:
If you ever went to one of those "smart bars" in the late 90's, theres a good chance you tippled some vinpocetine. I'm not sure whether it's actually effective, but people have looked at it for everything from…
Sorry if you're sick of this, but I'm having fun. You might remember my post on Havidol. (see also this follow-up). Justine Cooper (presumably) left a comment on the initial post, plus the prescribing information (PDF) has been updated. It's still not quite right - here, apparently, is your…
I'm almost cheating, since this one is so closely related to cynarin. Chlorogenic acid is yet another compound found in artichokes, as well as coffee. In addition to modulating your ability to taste sweetness (though not in the levels or conditions found in coffee, it would seem), it has some…
I am always completely confused when I meet someone who doesn't like artichokes. Not in the cheese-based dip, though that's not bad, either. I take my artichokes steamed, with a big bowl of drawn salted butter. The savory-sweet taste, the smooth texture, that puzzling satisfaction of only getting a…
Great entry from Khymos last week. Isohumulone is a compound found in beer imparting some of the (good) bitterness. Unfortunately, the magic of photochemistry can wreak havoc on it.
Isohumulone can be excited by the agency of riboflavin, an endogenous chromophore, causing it to cleave into a pair…
See also this followup.
Take another look at the Havidol post's comments. It looks like the chemistry's not only a little bit off - some other parts of the site look a little familiar.
And by the way, it's HCl, not HCI.
Ammonium carbonate is analogous to the other bicarbonate and carbonate salts you see - baking soda. In the presence of acid; or just sufficient heat, it will offgas ammonia and carbon dioxide, hopefully leaving pleasing bubbles in whatever you're making.
Whatever you're making better not have much…
It's remarkable how different RNA and DNA are, considering they're just one atom different. RNA is much more prone to fall apart; you can put DNA in basic solution without any problem, but RNA will begin to hydrolyze. Life takes advantage of the ease with which RNA is degraded. It has a much more…
Denatonium, sold as Bitrex, is among the most bitter compounds in the world. Why in the world would industry seek out such a thing? To put in things we don't want you to eat, silly.
I think it was developed to denature nonbeverage alcohol (to avoid having to pay alcohol tax, booze not intended for…
See also the followups (one, two) to this post.
From the taking jokes too seriously department...
Havidol is a fake drug campaign by Justine Cooper that's on display in NY at the Daneyal Mahmood gallery (warning, slow loading, natively embedded video). It seems like a pretty well-done faux-drug…
Cinnamaldehyde is a straightforward-looking molecule:
It's the principal odorant in cinnamon. If you're in the Seattle area, your cinnemaldehyde use is being monitored. Drug precursor? Guess again...
Cinnamaldehyde is oxidized in vivo to cinnamic acid, which you excrete in your urine:
Rick Keil…
Busy couple days. You get some odorants.
For historical reasons, some fragrance contains ingredients inspired by the odor of (or originally found) in a gland in a certain species of false deer. The deer and fragrance are called musk. One substantial contributor to the natural fragrance is muscone…
Reichardt's dye is pleasing in structure and function:
It is related to yesterday's molecule, betaine. It is technically a "betaine," but in a much broader sense, since it is an ammonium zwitterion (has a positive and negative charge). It posesses the property of solvatochromism - that is, it…
Betaine is a simple little molecule:
It finds use in medicine in treating elevated homocysteine levels - a molecule that deserves its own entry. It also can act as a denaturant - things like urea, formamide, and guanidinium are useful for this in biology. Betaine, at the right concentration, can…
As discussed in the entry on telomestatin, drugs that bind to guanine quadruplexes are of a lot of interest. One model compound is TMPyP (tetrakis(N-methylpyridyl)porphyrin)). The idea is that the big aromatic porphyrin surface stacks on the guanines, and the positive pyridinium moieties are near…
Buffers are a bit tricky. In biology, a buffer contains at least one ingredient: something to set the pH. This means having something that ionizes (takes on or loses a proton) at about the pH you want. You can set the pH within about one unit of this value (the pKa). This constraint exists because…
You know a compound has a story when nobody calls it by a chemically descriptive name (or the inventor's name). Proton sponge, or 1,8-bis(dimethylamino)naphthalene, is one such compound.
Proton sponge was discovered in Roger Alder's lab in 1968. It is a non-nucleophilic base (like DBU), which, as…
Chromated copper arsenate is an interesting one. It is a mixture of the copper salts of chromic acid and arsenic acid.
CCA provides robust protection against the sun, fungus, and bacteria. Unfortunately, chromium (VI) and arsenic are quite toxic, and can leach from the wood.
One problem with wood…
Jasmone is an odorant constituent, of, unsurprisingly, jasmine flowers. It's somewhat unique by virtue of its biosynthetic pathway.
Back with a full entry tomorrow.
I swore I posted this yesterday, but there's no sign of it. Thanks to Hillary for prodding me...
Titanium isopropoxide is a Lewis acid and useful in organic synthesis for this reason. It's also useful for synthesis of various titanium compounds.
Another neat thing about Ti(OIPr)4 is that it…
Thionyl chloride is one of the classics of organic synthesis - it is a robust reagent for converting carboxylic acids into acid chlorides.
I think it smells unpleasantly like buttered popcorn (mutiple people have told me I'm crazy for thinking this, but I insist it's there). There is a definite…
The automated chemistry for making DNA uses special monomers called phosphoramidites. To make this, you have a nucleoside (a DNA base + a DMT-protected sugar - everything but the phosphate) - and couple it to a phosphoramidite chloride. Once you've made (and purified) this, it's ready to go into a…
I don't have much to say about acetophenone chemically - It is a useful (and very common) synthetic precursor. It's one of a relatively few chemicals that aren't used as a solvent that many labs keep around in liter bottles. The main reason I like it, though, is that it smells wonderful.…
Piperidine is a useful little heterocycle - Walter Gilbert won a Nobel Prize, due in part to his development of a method of sequencing DNA (which uses piperidine as a base). It also has some use in peptide synthesis. Piperidine is also a very useful thing to hang off a drug, because it adds some…
Benzoylecgonine is the primary metabolite of cocaine - it's actually just cocaine minus a methyl group. It's not really used as an intoxicant, but it does have one interesting use: figuring out just how much cocaine people are using.
One study in 2005 in Germany examined the total amount of…
Basicity and nucleophilicity are two related concepts, but they don't always correlate. This is part of what makes teaching and learning chemistry so tricky, especially at first, when it seems like you're just learning a collection of facts (rather than the holistic wonder that is chemistry!). A…
Brodifacoum is warfarin's mean sibling: it is another vitamin K analogue. It's so potent and has such a long half-life (on the order of months!) that it's more of a poison than an anticoagulant. It's used for the expected things; as a rat poison, etc. Interestingly, despite its lavish toxicity, all…
Warfarin belongs to a previously-covered class of molecules known as the coumarins. Coumarins see use both as anticoagulants (in people) and poisons (in certain small animals).
Warfarin works by inhibiting a crucial step in vitamin K metabolism. Its structure isn't so far off:
Vitamin K is named…
Nickel tetracarbonyl, like a lot of metal carbonyls, is an odd duck. Many complexes of metals and carbon monoxide don't act much like metal at all, and Ni(CO)4 isn't an exception. Nickel carbonyl is a liquid, but only just - it boils at 43C, or just above blood temperature. It's subject to lots of…
Sodium bisulfite is a decent reducing agent, but lots of synthetic chemists know it as a convenient (and positively ancient) reagent for forming derivatives of aldehydes, which are useful preparatively. When you treat an aldehyde with NaSO3H, an insoluble adduct often precipitates, leaving behind…