Transcript Organic chemistry of sugar

Organic Chemistry of Sugar
Presented by: Amber Lloyd
Purpose
Saccharin
Aspartame
Sucralose
Sucrose
Why is this important?
 Natural vs. artificial controversy
What is sugar?
 Typically refers to all carbohydrates
 General formula:
 Cn(H2O)n
 Are all sweeteners carbohydrates?
Image source: http://333oee3bik6e1t8q4y139009mcg.wpengine.netdna-cdn.com/wp-content/uploads/2014/03/sweeteners_sugar.jpg
The Original Sweetener -- Sucrose
 Composed of 2 monosaccharides
 Structural differences between:
 Raw vs. refined?
 From sugar cane vs. sugar beet?
 Primary reference for other sweeteners
http://www.wpclipart.com/science/atoms_molecules/molecules/sucrose.png.html
Synthesis of Sucrose
 Formation – Dehydration Reaction
Artificial Sweeteners
Focus on: Sucralose, Saccharin & Aspartame
Sucralose
 “Cousin” of sucrose
 Structurally the most closely related
artificial sweetener
 Sweetest sugar derivative
http://www.zoetstoffen.nl/sites/zoetstoffen.nl/files/zoetstof/sucralose2.png
Synthesis of Sucralose
 Starting material?
 Why so many steps to
replace 3 –OH with
–Cl?
http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392
Saccharin
 Health benefits instead of dangers?!
 Presidential support
Synthesis of Saccharin
Original Method
Maumee Method
Images: http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392
The Current Face of Controversy -- Aspartame
Image: http://collectivelyconscious.net/wp-content/uploads/2014/05/new-study-fda-approved-levels-of-aspartame-distort-brain-function-kill-brain-cells2.jpg
Aspartame (continued)
 Composed of 2 amino acids
 Real fuel behind the controversy: side
products produced during degradation
Synthesis of Aspartame
 Two methods of
production
 Coupling vs.
Enzymatic
Conclusion
Structurally similar to
Sucrose?
Sucrose
Sucralose
Yes
Saccharin
No
Aspartame
No
Able to be
metabolize?
If yes– into what?

Glucose & Fructose

Aspartic acid,
phenylalanine, and
methanol
Written Assignment
 I am proposing to create a children’s book that looks at the sweeteners discussed during
this presentation in a colorful way. The goal of this children’s book would be to capture the
interest of young scientist in such a way that they can really see and understand how
natural and artificial sweeteners are truly different on a chemical level.
References
 McGuire, Michelle. Beerman, Kathy A, Nutritional Sciences: From Fundamentals to Food;
Wadsworth, Cengage Learning: 2007.
 Ouellette, Robert J., Rawn, J. David. Organic Chemistry: Prentice Hall; 1997, pg 759-762
 Belitz, H.D,, Grosch, Werner, Schieberle, Peter. Food Chemistry, 3 Ed; Springer Science and
Business Media: 2009, pg 868-875
 McMurry, John. Fundamentals of Organic Chemistry: Cengage Learning; 2010, pg 490
 Solomons, TW Graham; Fryhle, Craig B. Organic Chemistry 11 Ed : Wiley: 2013
 Cheminfo2011: http://cheminfo2011.wikispaces.com/page/diff/Yiwei+Wang+Final/281722392
(accessed: November 1, 2014)
 Saccharin information center: saccharin.org (accessed: November 1, 2014)
 Aspartame information center: aspartame.org (accessed: November 1, 2014)