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JCE Featured Molecules

William F. Coleman
Wellesley College
Wellesley, MA 02481

Molecular Models of Components

in Red Bull Energy Drinks
March 2009 Featured Molecules
Our featured molecules for this month come from the
paper by Andr J. Simpson, Azadeh Shirzadi, Timothy E. Burrow, Andrew P. Dicks, Brent Lefebvre, and Tricia Corrin (1). In
the article, the authors describe the use of NMR to identify and
quantify a number of components in the energy drink Red Bull,
in both regular and sugar-free forms. Some of these substancesglucose, sucrose, caffeine, and methylcobalamin (vitamin
B12)are already in the JCE Featured Molecules collection,
and we add twelve additional structures this month (2).
Although the NMR experiment is designed for upper-level
undergraduates, Red Bull and energy drinks in general as well as
several of the components of Red Bull offer interesting possibilities for study across the curriculum, starting at the pre-college
level. The drink itself and component species including taurine,
aspartame, and the potassium salt of acesulfame (often referred
to as acesulfame potassium in that reverse nomenclature used by
the drug industry) have a life of their own in the internet world
of pseudo-science and urban legend. It is never too soon to
begin to help students learn to navigate the pot-hole filled road
that is the information highway. A discussion might begin with
a simple questionWhat have you heard about Red Bull?
or What have you heard about aspartame?. One could then
proceed to explore the claims made about the health effects of
these substances, and move in the direction of finding reliable
information to support or refute these claims. As much as we
might like our students to rely solely on the primary chemical

Taurine is a major constituent of bile and can

be found in the lower intestine and in small
amounts in the tissues of many animals and
humans.

literature as their source of chemical information, the fact is that

the Internet is where almost all of them go first when researching
a new topic. Of course, that is true of most of us as well, but we
have the tools to separate wheat from chaff, and the majority
of our students do not. If we dont ask our students how they
analyze information, we will never know what myths they continue to believe. This was recently illustrated for me in dramatic
fashion when an astrophysicist colleague told me that despite
his very best efforts, a number of his students in introductory
astronomy still clung to doubts about moon landings.
The featured molecules this month suggest other activities.
Students in introductory or analytical chemistry could be asked
to measure the pH of various drinks containing citric acid or
citrate ion, and to then calculate the distribution of the various
citrate species at that pH. It would also be instructive to have
students consider why the pKa values for citric acid (3.1, 4.8,
and 6.4) are more closely spaced than those for phosphoric acid.
The inositol structure that is included here is the myo-inositol
isomer. Students in organic or physical chemistry could model
structures of other isomers and compare their energies to this
predominant form. The sulfuroxygen bond in the acesulfame
anion is quite long (177 pm) when computed using density
functional theory, the B3LYP functional and a 6-31G(d,p) basis
set. An interesting question would be whether or not this bond
remains unusually long in other compounds where the oxygen
is also part of a ring system.
Literature Cited
1. Simpson, Andr J.; Shirzadi, Azadeh; Burrow, Timothy E.; Dicks,
Andrew P.; Lefebvre, Brent; Corrin, Tricia. J. Chem. Educ. 2009,
86, 360362.
2. Glucose, sucrose and caffeine are in the April 2007 JCE Featured
Molecules collection at http://www.JCE.DivCHED.org/JCEWWW/Features/MonthlyMolecules/2007/Apr/index.html and methylcobalamine is in the July 2003 collection at http://www.JCE.
DivCHED.org/JCEWWW/Features/MonthlyMolecules/2003/
Jul/index.html (both sites accessed January 2009).

Supporting JCE Online Material

http://www.jce.divched.org/Journal/Issues/2009/Mar/abs400.html
Full text (HTML and PDF) with images in color

Links to cited URLs and JCE article

Aspartame is the name for an

artificial, non-saccharide sweetener,
marketed under a number of
trademark names, including Equal,
NutraSweet, and Canderel.

400

Supplement

Find Molecular Models of Components in Red Bull Energy Drinks in the JCE Digital Library at http://www.JCE.
DivCHED.org/JCEWWW/Features/MonthlyMolecules/2009/
Mar/

The molecules added to the collection this month are:

acesulfame anion; aspartame; citrate ion; citric acid; -dglucopyranose; -d-glucopyranose; glucuronolactone; myoinositol; niacin (vitamin B3); pantothenic acid (vitamin B5);
pyridoxine (vitamin B6); taurine

Journal of Chemical Education Vol. 86 No. 3 March 2009 www.JCE.DivCHED.org Division of Chemical Education