Saturday, March 30, 2013

Smells Like Satiety

The NYT Well Blog recently covered a fascinating study out of TUM* in Munich, Germany: olive oil may cause you to feel satiated faster and eat less food. Apparently, study volunteers fed yogurt with olive oil mixed in showed a spike in serotonin levels, and ate about 175 calories less each day than experimental groups given different fats (rapeseed, butterfat, or lard).

But was it the fat, or was it the flavor? The researchers isolated aroma compounds from the olive oil, specifically hexanal and 2E-hexenal, and mixed them in with yogurt. Same effects! In the press release, Prof. Peter Schieberle comments "Our findings show that aroma is capable of regulating satiety."

Smells rule neurochemistry. It wasn't that long ago, really, that Axel and Buck won the 
Nobel Prize for their research into olfactory organization. Two years later, another unsolved mystery, that of "blood smell," came to light in ACIEE. Turns out, both blood smell and the new research on olive oil aroma depend partially on medium-chain aldehydes (hexanal-decanal) and unsaturated ketones. You can even smell ketosis, an alternative metabolism found in diabetic crises and Atkins dieters, by the tangy, astringent odor on the breath. 

Amazing how sensitive the human nose is for volatile carbonyls! Perhaps this harks back to a rather strange notion of odotopes, or "weak-shape" theory. This suggests that, rather than the "lock-and-key" model observed for enzymatic binding, smell may result from a collection of weak interactions with multiple receptors, based predominantly on molecular shape. 

*Bonus note: I knew I recognized the TUM group from somewhere! Remember this abstract, from J. Agric. Food Chem. last year? Based on my (single, not to be repeated) experience with durian fruit candy, I do wonder how they convinced this poor scientist to be the GC smell-port 'volunteer.'

You couldn't pay me enough.
Source: Steinhaus, TUM | J. Agric. Food Chem 2012

More Car Talk "Chemistry"

Regular readers know my fascination for all things NPR, and Car Talk in particular. This week's broadcast had me rolling in the aisles for a different reason: some cover-your-eyes-awful chemistry.
A "white residue" in the engine?
Get the peanut butter!

Let's set the scene: Tom and Ray had taken a call from Ann, who begged that they were her "last hope" for an aging, ailing Subaru wagon. Ann's son apparently noted a funny white "mist" coming out of the car a few months ago. After several expensive repairs (heater core, radiator), a white, powdery substance was still forming in the engine block.

The guys considered that a single engine part had failed, perhaps something plastic or rubber, but discarded that theory since previous repairs had not fixed the problem. Then Tom suggested that the car might be continuously producing the white residue, perhaps through combustion gases which found their way into the radiator fluid through a leaky gasket.

Tom short-listed some potential combustion "bad actors" - carbon, carbon dioxide, carbon monoxide, nitrous oxide. Aha! The nitrous oxide must be forming nitric acid, thus corroding the engine block. "It's Chemistry 101!" he exclaimed.

Except...not. I know that nitrogen dioxide or NOemissions from cars generate nitric acid in the presence of water, but last I checked, whipped cream cans and dental offices everywhere remained safe from acidic corrosion.

Undaunted, through admitting "I have no idea, I'm just making it up," Tom pressed on: perhaps a salt, such as copper nitrate (a blue solid) or, even better, copper carbonate ("It just sounds more white, like sodium bicarbonate") gummed up the works. Maybe, since the heater core was made from aluminum, that was the culprit?

Tom: "What about aluminum carbonate, A-L two C-O three!"
...or, maybe Al2(CO3)3?

Finally, Ray chimed in: "MIT's on Line 1, they want their diploma back."

Happy Saturday,

Note: I paraphrased this conversation as best I could, since the recording hasn't yet appeared online. When it does, you can hear the full 3/30/13 episode at

Thursday, March 28, 2013

Can I Include My Wikipedia Page?

How often have you seen this old chestnut used when discussing hiring managers?

"They can't read, but they can certainly count."

Simple translation: When choosing between two similarly-qualified candidates, scuttlebutt suggests that the person with the most publications will advance to the next round of interviews. Of course, this begs another question...what counts as a "publication?"

Ask five scientists, and you'll get five different answers. Certainly, anything peer-reviewed merits inclusion. Ditto invited submissions, books, patents, reviews, or essays. But here's where the boundaries grow fuzzy. 

Can you include anything 'scholarly' on your CV to pad the stats?

[Insert embarrassing admission here]: I'm the guy who clicks on the "Show CV" link on faculty webpages. I find a strange (masochistic?) pleasure in comparing my career, such as it is, to those in similar age brackets or research areas. Certainly, these are folks who've played the game and won, so what do they choose to include? Here's a partial list: 

Publications "In press," "Accepted," "ASAP," "Proofs," "Submitted," "In Preparation"
Book Chapters
Conference Proceedings
Foreword / Introduction / Prologue
Newspaper or magazine articles
Book reviews
Research Summaries / Synopses
Blogs / Tweets / Comments

I'm sure I'm missing some; please suggest any others you've seen in the Comments section.

The simplest way to avoid any ethical boondoggles? Maintain separate lists of publications by type, or simply list "peer-reviewed" vs. "not." Will you be hired over the person who lumps 'em all together? 

Wish I knew.

Who Gets Hired Where?

Not to steal Chemjobber's thunder, but I can't resist the question: Does anyone know a reliable data set for industrial chemistry hiring?

Taking my cue from Paul's incredibly exhaustive list of 2013 moves and hires in the academic world, I baited Twitter with the question. CJ opined immediately, with an apt football analogy:

Dan weighed in with a tantalizing bon mot:
Is there a massive, unseen data set out there somewhere? [scratches chin, head...]

Straightaway, I can only think of LinkedIn, which suffers from being 1) voluntary, and 2) noisy data. Other sources might include faculty web pages (infrequently updated) or the C&EN Careers page (accurate, but limited). The ACS Employment and Salary Survey could track this, but I don't think it's granular down to the specific position and company. 

Readers: Does anyone know of a better way to collect this data? 

Update: CJ (correctly) points out that 'ACS Career Survey' isn't a real thing. Fixed, thanks!

Chemistry Bumper Cars II

For Bumper Cars I, click here.

Well, I was holding off until Spring had officially sprung, but they're coming too fast and furious to wait any longer. Thanks to Paul for starting the engine on this season of thrilling, chilling chemistry faculty moves!

I'm a visual learner and amateur cartographer-in-training, so let's chart out Paul's confirmed moves (as of March 2013):

(click to embiggen)


1. John (Wedge)Wood, CSU to Baylor
2. Corey (Saffron) Stephenson, BU to Michgan
3. Sharon Hammes-(Silver)Schiffer, Penn State to Illinois
4. Kyoung-Shin (Cherry) Choi, Purdue to UW
5. Shih-Yuan (Lavender) Liu, Oregon to BC
6. Patrick (Yale Blue) Holland, Rochester to Yale
7. Andrei (Teal) Tokmakoff, MIT to Chicago
8. Xiaoyang (Green) Zhu, Austin to Columbia
9. Glenn (Orange) Micalizio, Scripps FL to Dartmouth
10. Thomas (Tan) Albrecht-Schmitt, Notre Dame to FSU
11. Phil (Purple) Castellano, Bowling Green to NCSU
12. Jer(Red)my Smith, NMSU to Indiana
13. Adam (Brown)schweig, NYU to Miami
14. Paul (Pink) Cremer, TAMU to Penn State
(Update 3/29)
15. Brian (Olive) Shoichet, UCSF to Toronto

Commentary: Most of the "action" seems constrained to the Eastern seaboard so far this season. In terms of overall distance, Prof. Liu takes the cake (3,000 miles), with runner-up (just added: Brian Shoichet, at 2,300 milesProf. Zhu (1,800) and Micalizio (1,400). This time around, there isn't so clear a trend of moving "up the ladder" rankings-wise or towards warmer climes; folks move everywhere! (Readers, if you spot a trend in this messy data, let me know in the comments)

Craziness: This only represents movement for the past seven months! Who knows what the rest of 2013 will bring? Tune in for the next exciting Chemistry Bumper Cars installment.

Thanks again to ChemBark for starting the conversation.

Update, 3/29 - Paul's site brought word of Shoichet, and Andre the Chemist aggregated and scored the moves based on U.S. News departmental rankings. Well done!

Monday, March 25, 2013

Hawker's Talk Secrets

"My Chemical Romance Calls it Quits"
"My Chemical Romance, In Memoriam"
"My Chemical Romance Break Up"

Never fear, dear readers: My 'chemical romance' continues unabated...[rimshot]

At the risk of sounding like a lounge act, I realize that clear communication supports good relationships. So, apparently, does Craig Hawker, an accomplished polymer scientist at UCSB. I've seen him present a few times; the man gives one hell of a talk!

This month, he shares his secrets with you courtesy of a (free!) Angewandte Chemie editorial. Building off the success of Whitesides' essay "Writing a Paper", Hawker points out a crucial difference:
"While a publication can be read again and again, a presentation is over immediately. Therefore, the rules for writing a publication differ from those for preparing a presentation."
Amen! We've all attended deadly discourse disasters: The 9AM conference sleeper. The 4PM no coffee, no snack, sotto voce speaker with tiny font. The don't-stop-for-questions local section dinner meeting. All tragic wastes of opportunity.

"Chemistry? Chemistry? Chemistry? Chemistry?"
Source: Ferris Bueller's Day Off
So, how can we improve?

Hawker offers several simple pointers, divvied up into two major sections ("The Slides" and "The Talk"). For slides, he argues clarity, simplification, and increasing "signal-to-noise" improves the amount of useful information instilled in the audience.

For speech, Hawker advocates skills that would play well in any concert hall: Practice. Engage with the audience, which includes eye contact and interaction. Project confidence. Modulate your voice, and know when to make use of silence.

Most importantly, argues Hawker, we must solicit active feedback. Like late NYC mayor Ed Koch, ask your audience "How'm I doin'?" An honest answer here may sting, but will help you to improve for next time.

Friday, March 22, 2013

Friday Fun: 404

Woke up a bit early, and wanted to check something out over at Apparently, when they perform required maintenance, this graphic comes up instead:

Well played, ACS.

Happy Friday, everyone!

Friday, March 15, 2013

Please Set Me Straight on Synthetic Yellow Dyes

Dear Ms. Hari and Ms. Leake,

Good evening. Earlier tonight, I read your petition calling for a ban on Yellow #5 (tartrazine) and Yellow #6 (Sunset Yellow) in Kraft Mac & Cheese. I must say that, while not a mac connoisseur myself, I have certainly eaten it once or twice. Furthermore, I agree that all processed food companies should periodically review their popular brands, taking into consideration consumer sentiment, and should make every effort to produce quality goods. 

Since your petition now has well over 230,000 signatories, I assume many in the general public agree with us. But I must know: Where did you source the scientific data for your claims?

Let's start from the top:

"Artificial food dyes...are man-made in a lab with chemicals derived from petroleum (a crude oil product, which also happens to be used in gasoline, diesel fuel, asphalt, and tar)."
Well, I can't disagree with the first part - they're certainly synthetic azo dyes. However, I'd like to discuss your second point, where you equate 'petroleum-derived' to well-known flammable, smelly, or oozy black 'chemicals.' These azo dyes don't really resemble the compounds you've mentioned at all - gasoline and diesel are long saturated chains of carbon atoms, while tar / asphalt are collections of polycyclic aromatic hydrocarbons (PAHs), which might resemble these dyes if you took just the naphthalene portion (right-hand side), deleted the "OH" group, and chained a whole bunch of 'em together.
Yes, azo dyes come from organic chemists (like me!) in a lab somewhere. But, you know what else comes from petroleum? Pharmaceuticals. Plastics. Cosmetics. Synthetic fibers. Coatings. Many of the modern materials you interact with on a daily basis.
"Require a warning label in other countries outside the US."
I believe the US also mandates (Code of Federal Regulations Title 21, section 74.1705) inclusion of tartrazine on labels - I've seen it listed on my mouthwash. (Incidentally, that same CFR page sets exacting limits on impurity content in these dyes)
"Have been banned in countries like Norway and Austria (and are being phased out in the UK)."
Are we just lifting directly from Wikipedia by this point? 
"Yellow 5 and Yellow 6 are contaminated with known carcinogens (a.k.a. an agent directly involved in causing cancer)."
Now here's where things get interesting. Head on over to TOXNET, the National Library of Medicine toxicology database. I've looked up both Yellow 5 (tartrazine) and Yellow 6 (Sunset Yellow), and I can't find any positive studies suggesting carcinogenicity. Ditto both Wikipedia pages, and even my copy of the Merck Index (13th Ed., pp. 9091 and 9157).
What about the potential impurities, you ask? Sunset Yellow can indeed be contaminated with Sudan I (see picture, above), a non-sulfonated version of the compound. Sudan I lists as a Class 3 Carcinogen, which (thanks, ACS!) means "unclassifiable as to carcinogenicity in humans." The European Food Safety Authority (EFSA) actually re-evaluated Yellow 6 in 2009, declaring an acceptable daily intake and noting Sudan I contamination was well below the allowed limit for lead in processed foods.
I won't argue against your claims regarding hyperactivity and allergic reactions; the Hazardous Substances Databank (linked through TOXNET) indicates several studies in which patients do indeed respond poorly to artificial dyes. However, I will note that the responsive patient percentages are often low, and many weren't deemed statistically significant relevant to placebo.
I don't disagree with consumers' rights to petition companies for product changes. But please, check the science, lest you lapse into harmful chemophobia.
See Arr Oh

Update (8:00AM 3/15) - @thefoodbabe contacted me on Twitter with the following: "you are incorrect in your critique of our petition, I've got to go interview live with CNN now - Ciao"

Update 2 (9:00PM 3/15) - CNN posted two responses to the petition.
One leans scientific, the other mostly re-states the bloggers' objectives.

Wednesday, March 13, 2013

Let the Sun Shine In

Have you ever wondered why so many chemicals are shipped in amber-tinted bottles? Turns out light can do some pretty sneaky unexpected chemistry.

Reporting in from scenic Switzerland, Gademann & Co recently disclosed a sweet protecting-group free synthesis of Taiwaniaquinol F, a 6-5-6 diterpenoid with "potent cytotoxicity" against certain cancer cell lines. They finish the target in 17 steps, highlighting a Wolff ring-contraction and a neato halogen-oxygen exchange. 

The authors note that the final isolation had to strictly exclude light, or else their product slowly decomposed. Luckily, they asked themselves " what?"

Source: Org. Lett. ASAP | Gademann group
Not to keep you in the dark; their product underwent a spontaneous 1,5 C-H remote functionalization. When the group tried to do it "on purpose" - placing a flask in the sun for 15 minutes - they were rewarded with a 30% yield of cyclized Taiwaniaquinol A.

The authors aren't quite sure what's so special about this system, but note a tantalizing biosynthetic possibility: since Taiwaniaquinol F comes from the bark of a certain tree, and "A" from its leaves, there's a real possibility that this process happens all the time in the plant! No enzymes, no metals, no bases. Just sunshine. 

Nature's amazing.

Habemus Chemia!

When the white smoke puffed up the conclave chimney, all eyes turned to the Vatican. A little while later, Jorge Mario Bergoglio - now Pope Francis* - emerged. His historic election as the first Pope from South America overshadowed another first: he's a chemist (Over at ChemBark, Paul had leaned in that direction earlier today, but I'm sure he was equally surprised)

Habemus Chemia!
Source: Guardian UK
Wikipedia, font of all things true and definitive, lists him as a graduate of the University of Buenos Aires, with an M.S. degree in the late 1950s. Ditto the Catholic News Service.

My Spanish is a bit rusty, but the Excelsior (Mexico) and 20Minutos (Spain) label him a 'chemical technician' and 'chemical engineer' respectively. Lisa Balbes helpfully points out that, according to ABC News, one of his first assignments in the church was teaching high school chemistry.

I tried to look up the Pope's peer-reviewed chemistry publications through SciFinder, Reaxys, and Google Scholar, but, alas, I'm unable to find any. Perhaps a more enterprising reader can clue me in if they're more successful...

*Though I'm not Catholic, I appreciate the influence and direction the Pope offers the faithful. I also find it exciting when chemists enter very public walks of life. See, for example, Jack Welch, Angela Merkel, or John Kuhn.

Sunday, March 10, 2013

"Under 40" Biotech Billionaires?

I assume he started young.
Credit: Forbes
Since the dawn of capitalism, Americans have been entranced by rich youngsters. Their quirks, foibles, and outrageous lifestyles make magazines' front pages and serve as cultural touchstones; Richie Rich, Eloise, Bruce Wayne, and Montana Max all represent the genre well.

Forbes recently got into the "Youngest Billionaires" game, with the 2013 list featured prominently on the website. Forbes profiled 29 individuals under 40 with net worths >$1 billion, whose life stories reveal several interesting trends.

How does one become an "Under-40" billionaire?
  1. Drop out of college to start a tech firm, or
  2. Inherit your wealth.
That's just about everyone on the list. By 'tech,' I mean computers, gadgets, or apps - nary a biologist or chemist among the ranks (there are three engineers, but they've made their fortunes on the business side of things).

Thought Experiment: What would one need in order to be a baby-faced biotech billionaire? 
(For the purposes of this exercise, we'll ignore inheritance, and focus on "bootstrapping" from a standard middle-class childhood.)

For one, you'd likely need to forego college, and probably grad school. A five-year Ph.D., coupled with a 3-year postdoc shaves eight potentially game-changing years out of your 20s and 30s. Not to mention you're still paying back student loans and likely making below-market wages the entire time. Make no mistake, you'll have to start early, and perhaps look to hire your Ph.D. friends on the other side.

Next, you need what folks in the tech sector call a killer app. What does that mean for biotech? Something cheap to produce, easy to sell, relatively non-toxic and easily handled, and usable by people around the globe. A simple cancer diagnostic, perhaps, or a revolutionary photocatalyst. Maybe a new strain of fungi or bacteria for food production, or a serendipitous discovery of a new dye or drug (Hey, it worked for Perkin!)

Credit: Shutterstock
Third, since you'll have to weigh each wild idea or ground-shaking concept you create against its future commercialization value, you'd need a fundamental shift in your view of scientific communication. Open-access journals, blogs, national meeting presentations? Not for you. Timely patent applications and I.P. guardianship will be your bread and butter, so no sense in risking inadvertent disclosures. 

So, follow these easy 1-2-3 steps to biotech billions, right? Well, of course it's never that easy. Luck plays a crucial role in start-up ventures, as do connections. In this field, one's credibility might be undermined without a college degree, which might make initial fundraising tough. The barrier to entry might also be too high; tech entrepreneurs can start with a laptop, but biotech needs lab space, reagents, journal access, safety gear...the list goes on and on.

Readers, I'm sure this sounds nice and logical on paper, but I must have missed something along the way. Can you think of any high-net-worth youngsters who cut their teeth in chemistry? Why don't more young people see science entrepreneurship as a valid career direction?

Monday, March 4, 2013

(Monday) Fun: Axe Cop Chemophobia?

c. Ethan Nicolle
Somehow, in all the rush to get Blog Syn #003A out the door, I totally missed my chance to post 'Friday Fun' on 3/1!

I may have mentioned (once or twice) my love for Internet comics. Specifically, I tend towards science-y ones, like xkcd or Ph.D. Comics, but for a complete change of pace I turn to Axe Cop.

Not familiar? It's an over-the-top parody about a super-powered policeman, who travels to other planets and meets lots, unique crime fighters. Even better? It's coauthored by a 32-year-old cartoonist Ethan Nicolle and his 8-year-old brother, Malachai.

c. Ethan Nicolle

Now, Axe Cop always runs ridiculous, but one panel from the latest story arc (Axe Cop Gets Married) made me wonder. In the scene, a group of 'scientists' at an 'Atomic Science Lab' (again, written by a kid) are mixing chemicals when something goes horribly awry. The lab explodes, and the survivors mutate into animal-human hybrids.

Ridiculous? Unlikely? Sure. Funny? Of course!

But also a little bit sad - how young do we start to infer that chemical means something bad for you?
(Apparently around 8, I guess)

Happy Friday Monday!