Noble Chemicals

I swear this post is not about noble gases. But if that’s what you were looking for, I have recently discussed the original Bohr model of argon and how the discovery of the noble gases could feature in my general chemistry course next year.

Instead, I was surprised to see “Nobel Prize winner introduces skin care line” in this week’s Chemical & Engineering News. The prizewinner in question is J. Fraser Stoddart, famous for molecular machines, a crest in the nanotechnology wave. The company is PanaceaNano. The skin care line is branded NOBLE with a square diamond in place of the O. The square represents the “organic nano-cubes” that deliver the appropriate rejuvenating molecules.

I used the word nano thrice in the preceding paragraph. So let’s define it before we move further along. A nanometer is 10^-9 meters (or 0.000000001 m). Think nine decimal places for nano. That’s the size of most relatively small molecules, i.e., the realm of the nanoscale. To get a sense of how these exponentials compare to the sizes of different objects, I highly recommend the animation Powers of 10.

The Noble Skin Care website has a slick video to explain their chemistry. The opening scenes trade on Sir Stoddart’s name and Nobel, as if to give the stamp of approval that their product uses Nobel-worthy cutting-edge chemistry – and therefore one can charge higher prices for such a premium product. No details are given in the video of the organic nanocubes, other than their size (3 nm in length), but they are represented as cubes. The C&EN article mentions that they are cyclodextrins. So not cubes per se, but container-shaped molecules that can be used for drug-delivery among other things. I considered them in my potion design example for one of my classes but went with a polycaprolactone instead. Here’s a Wikimedia commons picture of the cyclodextrin molecule and its approximate “container” shape.

In my chemistry for non-science majors courses, I have the students watch some videos promoting pseudo-scientific concepts. In the past, I’ve mainly aimed at water products since they are ubiquitous and popular. Penta water has been the poster-child offender for a number of years but Alkaline water is the rising fad. Some of the videos are slick, while others are clumsy. My goal is to have students look past the slickness and ask questions about the chemistry presented. They should not just believe the talking head’s scientific claims. Most of the talking heads in the nanoscale water products have dubious scientific credentials. Stoddart, on the other hand, has a Nobel prize along with an array of top-notch scientific credentials. He doesn’t function as a talking head in the video, although he is chief technology officer and co-founder of PanaceaNano. Is nanoscale chemistry a panacea or will it overrun us with evil nanobots? It’s too early to tell. But the company “chose to make its first commercial product a line of cosmetics because of the high margins and the ease of market entry.” Money first. World domination later.

The scene that caught my eye in the video was the molecules, so I took a screenshot (above). What are these molecules? Can I use this video as an exercise in my class and have my students hunt down the identities and uses of each substance? Can they use their background of rather limited (3-4 weeks) of organic chemistry and functional groups? How long would it take me, a physical chemist (i.e. not an organic or biochemist), to identify these? What strategies would I use? Well, I decided to put it to the test.

I could easily identify lactic acid, salicylic acid and retinol right off the bat; 3 out of 10 with no extra work (though this would not be true of my students). With retinol as a clue that vitamins were involved, it took me just a few minutes to identify ascorbic acid, niacinamide (B3 derivative), and what looks like a B6 derivative. Then it took some staring at the trihydroxy stilbene molecule, which looked very familiar, before I figured out what it was. However, I had to make use of my own background knowledge of what might be in anti-aging skin-rejuvenating creams. It also took some staring before I identified ubiquinone. Next I tackled the polymer. I could see it was a disaccharide of glucose and GlcNac (glucosamine), but I had to rack my brains a little. Then in a flash of insight, I remembered that four years ago, one group in my class decided for their final project to look at hydration creams. They even asked me about this specific compound, and then the name popped into my head. Chance favors the prepared mind, perhaps? Not sure how that memory ball was accessed.

So in maybe 15-20 minutes, I had 9 out of 10. (Okay, maybe 8.5 because I couldn’t directly identify the B6 derivative by a common name even if I could tell you the IUPAC name.) I could not identify the last molecule and needed to do a web search to find out it was ferulic acid. A student without much chemistry background would not be able to find most of these (except for the smallest three) using a chemical formula search. They would need other clues. If I learned anything from this exercise, it was interesting to reflect on my search strategy and what background information I accessed.

Timed delivery and molecular precision are the two other factors pushed by the NOBLE video and website. Given the range of molecules and what I know about other skin rejuvenating products (that use the same range of molecules), I don’t think there’s anything more precise going on in the molecular interactions. The timed delivery is more interesting. Presumably one can tailor-make cyclodextrin derivatives that provide a slower release over a longer period of time. But that strategy also works of any container-shaped molecule you might use. Some chemist might actually come up with a cube although it would likely not be completely organic. By organic, I mean not containing any metals (rather than “natural”). From a design perspective, to get right-angled shapes, metal centers are almost always (although not exclusively) required. In any case, cyclodextrin is a good choice as a delivery agent as it is likely not to screw anything else up.

The alchemists of olde sought to synthesize the substance that would form the elixir of life. The nuevo nanochemists carry on the noble quest.