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The Washington Post‘s continued coverage of the massive Kellogg’s 28 million cereal box recall in June, when 2-methylnaphthalene from the packaging percolated into the cereal, and yesterday’s news that Congress is now investigating that recall are good reminders that for any food you consume, a small part of the wrapping inevitably ends up in your body, too. Ditto for pharmaceutical drugs.

Last summer I wrote about how food and pharma companies are starting to deal with these packaging leachables, and so a couple of people at C&EN asked me to speculate on how the 2-methylnaphthalene had ended up in America’s Froot Loops.

According to the Kellogg’s press release, the voluntary recall occured due to an “uncharacteristic off-flavor and smell coming from the liner in the package.” The CDC’s website notes that naphthalene is often found in moth balls and deoderant, but it can also be found in resin (presumably how Kellogg’s thinks the 2-methylnaphthalene ended up in the cereal box liner) and printing dye ingredients. Substituted naphthalenes have high vapor pressure, which means they can migrate through all sorts of packaging, including cardboard and polyolefins.

I have no reason to debate Kellogg’s conclusion that the 2-methylnaphthalene did in fact come from the cereal box liner. But I wonder if the company also checked into the possibility that the  2-methylnaphthalene came from printing dyes on the cardboard box, since dye ingredients have a particular penchant for slipping through food and pharma packaging of all kinds.
For example, last year Europe also had a cerealgate, when 4-methylbenzophenone was found in chocolate muesli–which is a granola-like breakfast cereal eaten with near religious fervor on the continent. In the European cereal recall, the 4-methylbenzophenone was a component of the printing ink typically found on the outside of the box that had migrated to the inside.

Another way for printing ink chemicals to enter food from cardboard containers is when the packaging is recycled from paper products that possess dyes containing the chemical. A quick web search brought up this, albeit 0ld, 1994 reference to rice and pasta contaminated by six diisopropylnaphthalenes which probably came from the recycled paper used to make the cardboard packaging.

When packaging printing dyes end up in food or drugs, it doesn’t always mean they’ve percolated through the packaging. Sometimes food and drugs can be contaminated by the way packaging is stored prior to use. For example, packaging is often rolled up or packed in such a way that the printed exterior is touching the non-printed interior, creating opportunities for printing ingredients to taint the side of the packaging which contacts or is closer to the product. This led to a major recall in 2005 of baby formula stored in Tetrapak packaging that had been rolled up in this way.

There are so many routes for packaging materials to enter food and drugs it’s a bit mindblowing: At a conference last spring in Barcelona for people in industry and regulatory agencies whose job it is to worry about possible sources of packaging leachables in pharmaceutical drugs, we heard ample examples. For instance, an FDA participant told us that a set of injectible protein drugs in disposable syringes were spoiled because a tungsten filament used to poke a hole through the tip of the syringe needle had left behind a tungsten oxide salt residue that later percolated into the liquid-drug formulation causing protein aggregation.

In the case of the Kellogg’s cereal, 2-methylnaphthalene caused some nausea and vomiting. What might it be next time? Here’s an extentive analysis by the Environmental Working Group that argues the FDA should do much more about chemicals that leach from packaging.

So, chemistry students, any way your department could credibly spend over $80,000 a year on booze?

Speaking of drinking, we read an interesting article on alcohol proof this week in the Washington Post. Proof, as you may recall, is simply the percent of alcohol times two (math even an organic chemist can do). Since alcohol is such a good solvent for flavor compounds, proof has been on the rise in spirits in recent years so that bartenders can produce potent potables that pop with flavor. Even alcohol levels in wine have been creeping up to deliver a bigger burst of fruit flavor.

Chemist and absinthe enthusiast Ted Breaux even weighs in with an explanation of why the green fairy boasts such a high alcohol content–136 proof. “You have to bottle it at high proof because of the herbs. You want clarity, and if the proof isn’t high enough, the compounds will deteriorate. The spirit becomes hazy with sediment, and it looks awful,” he tells the Post.

Finally, in a tipple trifecta, a former Amgen chemist is distilling his own whiskey in the unlikely state of Utah, reports the Thousand Oaks Acorn. I got a good giggle out of this amended quote from chemist-turned-whiskey-maker David Perkins: “Making whiskey is a lot more fun than (pharmaceutical) drugs, as you get to taste the results as well as the in-between experiments.”

You may be surprised, however, to find out that even the same product sold in different countries can contain different ingredients. A recent article in CNN.com pointed out that Chicken McNuggets sold in the U.S. contain more calories and saturated fat than McNuggets in Great Britain. What’s more, American McNuggets also contain the preservative tertiary butylhydroquinone (tBHQ) and the anti-foaming agent dimethylpolysiloxane whereas British McNuggests do not.

In the article, Marion Nestle, a New York University professor and author of “What to eat,” recommended that readers avoid foods containing ingredients they can’t pronounce.

Is this really sound advice?

I was informed of this factoid this morning while I was eating my breakfast and watching CNN’s coverage of the oil spill in the Gulf. Reynolds Wolf (no relation, thank goodness), a meteorologist and CNN correspondent, was reporting from Louisiana on another chemical being used to help in the clean-up efforts: C.I. Agent.

We’ve already reported about the dispersants being employed down there, but I hadn’t heard of this substance until this morning. It seems clean-up crews are now also going to be using C.I. Agent, a petroleum-based blend of polymers that encapsulates oil (or any hydrocarbon, really), turning the whole complex into a rubberlike substance that can be scooped out of the water. This polymeric powder compound comes from Louisville, Ky.-based C.I. Agent Solutions, which says that the solidified oil-polymer product ”can be used as a fuel or sold to companies … as a filler to add strength and flexibility to their products.”

This is not exactly what Reynolds Wolf told me this morning. He stressed that the C.I. Agent is “a polymer, not a chemical” and that the final solid is “biodegradable.” I can’t find a video clip of this, so you’ll have to take my word for it, but I nearly choked on my cereal bar when I heard it. I’m guessing that what you were supposed to get out of all of this is something like: Chemicals are bad, but this polymer thing is good because it’s eco-friendly and helpful.

I talked all of this over with colleague Melody Voith, who authors the “Cleantech Chemistry” blog for C&EN. She’s already reported about other efforts to clean up the Gulf, such as stockings filled with hair, and looked further into this C.I. Agent here. 

I leave you with a video of C.I. Agent in action. It reminds me of one of those OxiClean commercials.

I can’t decide which headline about the study is more alarmist: Gothamist’s “Popular Veggie Burgers Contain Poisonous Chemicals” or Mother Jones’ “Which Veggie Burgers Were Made With a Neurotoxin?” The Village Voice’s “Enjoying that Veggie Burger? It May Contain Chemical Residues” just made me chuckle.

Anyhow, the chief complaint by Cornucopia is that the soy in many products has been washed in a hexane bath to extract fats. Hexane, Cornucopia notes, is bad for the environment and bad for you. Unless you’re eating soy products specifically labeled “organic” chances are you are eating hexane-extracted soy. And that goes for other soy-based foods and ingredients, such as soy baby formula and soy lecithin in chocolate.

Cornucopia didn’t actually see if any of those non-organic veggie burgers contained hexanes. They did test hexane-extracted soy oil, soy meal, and soy grits for the chemical and found soy oil contained less than 10 ppm of hexanes, while soy meal and soy grits had 21 pp and 14 ppm of the compound, respectively.

Although I’ve returned to the carnivore fold, I spent more than a dozen years as a vegetarian. I also spent five years as an organic chemistry graduate student, and I’d bet that I probably was exposed to more hexanes by running one column than I was through my cumulative consumption of Boca Burgers. But I am curious, anyone out there willing to test these burgers for hexane content?

UPDATE: Mother Jones has posted an update on their item about neurotoxin-laced veggie burgers in which they interview Charlotte Vallaeys, the author of the Cornucopia Institute’s report. Although Ms. Vallaeys holds an. M.S. in Agriculture, Food and Environment, I wish MJ had spoken to someone with a heftier chemistry background…and someone who wasn’t involved with the study.

When asked about the point that Chemjobber makes, Vallaeys responds: “The evaporation argument is often used by the companies that make these products. But what happens to the food when you cook it with this neurotoxic compound? Does it react with other substances and create new compounds before it evaporates? That really has not been studied.”

Vallaeys argues the bigger picture is that any product made with hexanes contributes to air pollution, but she seems to be a little confused about just what hexane is doing the atmosphere. In the report, she writes, “In the air, hexane reacts with other pollutants such as oxides of nitrogen to form ozone.”

It isn’t just an academic question. A movement to cut sodium intake in the population at large is afoot. It’s based on public health data that say lowering NaCl consumption in a population lowers blood pressure on average, and can thus reduce the risk of diseases such as stroke. And
it involves chemists, from those trying to determine how we taste salt to those working on making salt taste enhancers.

Since C&EN last blogged about this topic, New York City mayor Michael Bloomberg revealed an initiative to prod food manufacturers and restaurants to reduce the amount of salt in their foods. It’s not a new law, so compliance is voluntary.

The latest from the Times asks whether it’s even possible to get America to permanently cut its salt intake. Perhaps people would just eat more of everything, or go for saltier foods, to compensate, the article says.

I would’ve liked to see a link to the report out of Britain that the column mentions. This report was said to conclude that Britain’s more intensive salt-reduction effort is translating into a 10% decrease in daily salt intake, as measured by the amount of salt excreted in urine. (Now there’s a job for the new guy in the lab..) I haven’t found this report yet, but I will update if I do.

I don’t know much about public health, but the call at the end of the column for a randomized clinical trial on salt intake makes sense to me. I was surprised that this hasn’t been attempted, and my cursory search at clinicaltrials.gov shows that researchers are trying, sort of. See here and here. Only one of the two trials appears to be randomized, and neither claims to be double-blind.

More reading:

The (Political) Science of Salt – reporter Gary Taubes delivers what I still think is the most measured assessment of the ‘salt wars’. This article is over ten years old though, so take it as an introduction and read some more recent work, too.

Institute of Medicine of the National Academies – the health arm of the National Academy of Sciences. Here you’ll find reports and information about meetings on developing strategies for salt reduction. Searching the site for ‘sodium’ is a good start.

The Salt Institute – a nonprofit organization of salt companies.

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Unlike the Sangji article, this story from Friday was about something I’d never heard of before- during Prohibition, the U.S. government ordered the adulteration of industrial alcohol in order to thwart bootleggers and stop people from drinking. As author Deborah Blum explains, that didn’t go so well. Poisoned holiday revelers died by the dozens in the nation’s hospitals. And outraged public health officials and anti-Prohibition legislators had harsh words for the government’s ethically dubious chemistry dabblings.

Since most liquor syndicates were simply taking denatured industrial alcohol, which has additives put in to make it undrinkable, and distilling it to remove said additives, the feds decided to make that distillation a bit more complicated.

From Blum’s article:

By mid-1927, the new denaturing formulas included some notable poisons—kerosene and brucine (a plant alkaloid closely related to strychnine), gasoline, benzene, cadmium, iodine, zinc, mercury salts, nicotine, ether, formaldehyde, chloroform, camphor, carbolic acid, quinine, and acetone. The Treasury Department also demanded more methyl alcohol be added—up to 10 percent of total product. It was the last that proved most deadly.

A couple of chemistry thoughts went through my head as I read Blum’s piece:

How easy is it to separate methanol and ethanol? I pulled out my CRC Handbook, checking to see whether there was an azeotrope- there was none to be found. I also dug up this brochure. Anybody out there know how this works?

The strychnine mention recalled a lecture on poisons I attended several years ago. The professor who gave the lecture told the crowd that the lecture was a favorite of undergrads. I could see why. He started off dramatic, pacing the front of the room with a white coffee mug filled with water and a small, non-lethal (he assured us) dose of strychnine. Then he had us dip a finger in the mug and taste it. I am not making this up. Whatever was in that mug was bitter almost to the point of gagging. The professor explained that at a lethal dose of strychnine, the bitterness would be overwhelming, so it wasn’t a perfect poison, as poisons go. The stuff probably was strychnine- The Merck Index writes that a solution containing as little as 1 part strychnine to 700,000 parts of water will still taste bitter.

Brucine, the alkaloid mentioned above, is a little less bitter than strychnine (the threshold for tasting bitterness in the tetrahydrate is 1:220,000, again per the Merck Index). But I’m guessing that for the poor souls drinking that bootlegged swill, bitterness was the least of their problems.

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When the Consumer Product Safety Commission set lower limits on the amount of lead allowed in U.S. toys, some Chinese manufacturers apparently began using cadmium instead. Cadmium is cheap, but it’s also toxic.

According to the Occupational Safety & Health Administration, cadmium is “a soft, blue-white malleable, lustrous metal or a grayish-white powder that is insoluble in water and reacts readily with dilute nitric acid.” Cadmium metal is primarily used because of its anticorrosive properties. It is found in alkaline batteries, pigments, metal coatings, plastics, and now some children’s toys imported from China.

Cadmium is considered a known human carcinogen by the Department of Health & Human Services. Long-term exposure to the metal can lead to kidney disease, lung damage, and fragile bones, depending on the route of exposure.

The question is whether a child is likely to be exposed to cadmium in toys. Wearing a necklace or bracelet is unlikely to cause harm, but sucking on a necklace, or swallowing a piece of it, would certainly be a different story.

In October, bright orange pumpkin erasers with extremely high levels (1800 ppm) of cadmium were in the news. I happened to have a few of them around my house from birthday party goody bags my kids brought home. Out of concern that my kids would chew on them, I threw the erasers out in the trash.

Someone ought to calculate how much cadmium is likely to enter landfills because of the recent cadmium jewelry scare, and what impact that could have on ground and surface waters.

Fuchs is a physical chemist who leads a molecular simulation group at Chimie Paris Tech, and is also the university’s director. Chimie Paris Tech is part of a distinguished and influential group of higher learning institutions in France called “écoles nationales supérieures.” According to Le Monde, a mathematician named Antoine Petit and a cryptologist named Jacques Stern were also considered for the CNRS position.

Whoever gets the job will be responsible for 26,000 permanent CNRS staff and a budget of 3 billion Euros ($4.3 billion). That person will also be at the helm of an organization in transition: The French government is splitting the CNRS into 10 institutes by subject. For example the institute of chemistry will be separate from the institutes of physics and biological sciences.

The new CNRS director general-president will be kept busy: The relationship between President Nicholas Sarkozy’s government and French scientists (including those from CNRS) has been rocky. Some of the government’s proposed reforms to the CNRS and to universities have brought thousands of scientists out of their labs and into the streets in protest.

A counterfeit drug manufacturing lab in Colombia

As I was doing interviews for an article on fake pharmaceuticals, Paul Newton told me a story that I am unlikely to forget. Newton is a doctor in Laos who is involved in several projects to track down counterfeit malaria drugs in Southeast Asia and Africa; he’s also a doctor at a Wellcome Trust-funded hospital that is associated with tropical medicine at the University of Oxford.

We were talking about the fact that nobody knows exactly how many fake drugs are consumed around the world, but it’s pretty clear that the problem is greater in developing countries where there is less funding for regulation and/or policing. (The WHO estimates that markets in industrialized countries such as the U.S. and many parts of the E.U. have no more than about 1% counterfeits. In developing nations, some 10-50% of pills are guesstimated to be bogus.)

“Counterfeiters have killed with impunity,” Newton said. He went on to tell me that people sometimes spend what little money they have to unwittingly buy fakes, and then have succumbed to otherwise curable diseases because the medicines have not worked. “A Burmese patient died a few years ago of malaria having clearly taken fake artesunate,” a malaria drug, Newton said. “When he was admitted with malaria all the signs were that he should recover rapidly but then he deteriorated and died of cerebral malaria very tragically,” Newton added. The man’s community was so upset that people in “the village where the patient came from took all the medicine he had been taking from the shop. They burned it in a bonfire in the village in a spontaneous protest,” Newton told me.

It’s stories like these that have motivated the WHO to team up with INTERPOL to form an international anticounterfeiting task force called IMPACT (International Medical Products Anti-Counterfeiting Taskforce). Drug counterfeiters pull in a–guesstimated again–$75 billion per year. According to many who follow pharmaceutical counterfeiting, hard drug traffickers are now turning to the business of making bogus medicines because the profit margin is better and the penalties are softer… than for say, cocaine or heroin. The IMPACT taskforce has just a couple of full-time staff members, which seems rather small for the challenge of coordinating the international fight against fake medicines. Yet IMPACT has brought down counterfeiting operations in Southeast Asia, Tanzania, Uganda and in Nigeria. Here’s a catch of bogus drugs, courtesy of IMPACT:

Fake meds in nabbed in Tanzania and Uganda

Here is an example of the storage conditions for fake medicines found in Kenya, also courtesy of IMPACT:

Storage of counterfeit drugs in Mombasa

And last but not least, here’s a shot of manufacturing facilities for a counterfeit ring tracked down in China. Photo courtesy of Pfizer’s David Shore:

Fake drugs, made in China

Even though it may seem like counterfeiting is on the rise, Newton pointed out to me that the business of making fake medicines is as old as remedies themselves. Around 1500 BC, an Egyptian queen called Hatshepsut got so fed up with the quality of herbal medicines she was exposed to, that she led an expedition herself to get good quality medicines in the land of Punt, near current day Somalia. More recently, in the 1600s, quinine-containing Cinchona bark imported to Europe from South America as treatment for malaria was adulterated “at such an enormous scale that the public gave up on the medicine because it seems not to work,” Newton adds.