intersection 5 10/3/05 reading: 9.6 p409 – 418; 3.12 p111-113 material for this lecture taken from...
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Intersection 5
10/3/05
Reading: 9.6 p409 – 418;
3.12 p111-113
Material for this lecture taken from Laursen, S; Mernitz, H. Would You Like Fries with That? The Fuss About Fats in our Diet; Wiley & Sons: New York , 2000.
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A Gateway to Information Storage and ExpressionHow does nature store and express information?
How does nature’s way compare to our computers and hard drives?What is the impact of this understanding and resulting technologies?
Special Guest: Dr. David Burke (UM Human Genetics Department)
6 – 7:30 PM Monday October 9th
Room 1230 USB
Please RSVP by email to Prof Banaszak Holl([email protected])
Gateway evenings are optionaland will not affect your course grade
Gateway Chemistry 130/125/126Section 600
Dinner Provided
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Outline
• Bond length • Molecular polarity• Intermolecular Forces
– The trio of forces
– Olestra
– Vitamins
– Macronutrients and diet• Betacarotene
• Vitamin D in OJ
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Bond Order
• Single bond - first order
• Double bond = second order
• Triple bond third order
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s orbitals
s + p orbitals
s + p + p orbitals
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Bond Length (pm): the distance between the nuclei of two bonded atom
H-F 92 C=C 134 C-O 143
H-Cl 127 C=N 127 C=O 122
H-Br 142 C=O 122 C≡O 113
H-I 161
C-C 154
C-Si 194 C-C 154 C=C 134
C-P 187 C-N 147 C≡C 121
C-S 181 C-O 143
C-Cl 176 C-F 141
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Polarity of Molecules: Maps of Electron Density
+ -
Br
FF
F
FF
C
H
ClCl
Cl
BrF5
CHCl3
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SCN-
S C N
-1
S C N
-1
A
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Is it SO2 or H2O?
H
O
H
A
S
O O
+1
-1S
OO
+1
-1
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Molecular Polarity
• NO2-
• ClF3
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Intermolecular Forces
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1) Why do we have to take some vitamins everyday (B and C), while our body stores others well?
2) Why are vitamins A, D, E, and K added to any products containing Olestra?
Picture from: http://enquirer.com/editions/2000/06/23/oleanproducts.jpg
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O
O
Vitamin K
CH3
H
CH2
HO
CH3CH3
CH3
Vitamin D
OH3C
HO
CH3
CH3
CH3
CH3CH3
CH3
CH3
Vitamin E
H3C CH3
CH3
CH3 CH3
OH
Vitamin A
N
N
N+
SH3C
NH2 CH3
OH
Vitamin B1
O O
OHHO
HO
HO
H
Vitamin C
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OlestraOlestra is a fat substitute developed by Proctor and Gamble and
used to make Ruffles WOW! Potato chips.
Serving Size 1 oz (28 g/ about 17 chips)
Total fat 0 g (Original Ruffles 10 g)Total Calories 75 (Original Ruffles 160)
Ingredients: potatoes, olestra (Olean® brand), salt, alpha-tocopheryl acetate (vitamin E), vitamin A palmitate, tocopherols (to protect flavor), vitamin K, and vitamin D.
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Hypothesis1) Why do we have to take some vitamins
everyday (B and C), while our body stores others well?
2) Why are vitamins A, D, E, and K added to any products containing Olestra?
• What is your hypothesis?
• How would you test it?
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Testing the HypothesisStep 1: Separate
– Vitamins added to test tube with water and ligroin and shaken…which layer is on top? How do you know?
Ligroin - a complex mixture which includes
H3C
H2C
CH2
H2C
CH2
H2C
CH3
H3C
H2C
CH2
H2C
CH2
H2C
CH2
CH3
H2C
H2CCH2
CH2
CH2
H2C
CH3CH2H3C
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Spectroscopy
Step 2: TestMolecules (containing double bonds) typically absorb
light in the UV region of the spectrum. Water and ligroin do not absorb light in the same region of the UV spectrum.
Shine UV light through the water layer or the “oil” layer sample to a detector
Measure the intensity of the light going into the sample and the intensity of the light coming out.
Determine if sample absorbed light
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RetinolCartenoids such as betacarotene converted to retinol
Vision bone growth, cell division and differentiation
Eggs, milk, liver, fortified cerealsCarrots, cantaloupe, sweet potatoes, and spinach
H3C CH3
CH3
CH3 CH3
OH
Vitamin A
A
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Vitamin A
-0.5
0
0.5
1
1.5
2
2.5
250 300 350 400 450 500 550 600
Wavelength (nm)
Abso
rban
celigroin
water
A
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Vitamin B1
Thiamine
Nervous systems, muscles, heart
Kidney, liver, flour, beans, pork, salmon, soybeans, wheat germ
N
N
N+
SH3C
NH2 CH3
OH
Vitamin B1
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Vitamin B1
-0.2
0
0.2
0.4
0.6
0.8
1
1.2
1.4
250 300 350 400 450 500 550 600
Wavelength (nm)
Absorb
ance
ligroin
water
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Vitamin C
Ascorbic acid
Anti-oxidant, free-radical scavenger
Pepper, citrus, tomatoes, melons, broccoli, green leafy veggies
O O
OHHO
HO
HO
H
Vitamin C
A
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Vitamin C
-0.5
0
0.5
1
1.5
2
2.5
250 300 350 400 450 500 550 600
Wavelength (nm)
Absorb
ance
ligroin
water
A
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Vitamin D
Group of steroids called cholecalciferol
Regulate calcium, phosphorous, bone mineralization
Enough sun and don’t need supplement; found in egg yolk and fish oil, fortified food products
CH3
H
CH2
HO
CH3CH3
CH3
Vitamin D
A
Reported soluble in ligroin
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Vitamin E
Alpha-tocopherol
Antioxidant
Vegetable oils, nuts, green leafy veggies, fortified cereals
OH3C
HO
CH3
CH3
CH3
CH3CH3
CH3
CH3
Vitamin E
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Vitamin E
-0.5
0
0.5
1
1.5
2
2.5
250 300 350 400 450 500 550 600
Wavelength (nm)
Absorb
ance
ligroin
water
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Vitamin K
Synthesis of proteins that regulate coagulation and anticoagulation
Leafy greens, cauliflower, liverSynthesized by bacteria in large intestine
O
O
Vitamin K
A
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Vitamin K
-0.5
0
0.5
1
1.5
2
2.5
250 300 350 400 450 500 550 600
Wavelength (nm)
Absorb
ance
ligroin
water
A
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O
O
Vitamin K
CH3
H
CH2
HO
CH3CH3
CH3
Vitamin D
OH3C
HO
CH3
CH3
CH3
CH3CH3
CH3
CH3
Vitamin E
H3C CH3
CH3
CH3 CH3
OH
Vitamin A
N
N
N+
SH3C
NH2 CH3
OH
Vitamin B1
O O
OHHO
HO
HO
H
Vitamin C
A
Water soluble (hydrophilic)
Fat soluble (hydrophobic)
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1) Why do we have to take some vitamins everyday (B and C), while our body stores others well?
2) Why are vitamins A, D, E, and K added to any products containing Olestra?
A
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ROO
C
CC
H
H
RO
H
O
ORH
CH2
HC
C
OR
C C
C
O
C
HOR
OR
H
CH2
CH2
H
RO
OR
R = C
O
CH2
H2C
CH2
H2C
CH2
H2C
CH2
HC CH
CH2
H2C
CH2
H2C
CH2
H2C
CH2
CH3O
H2C
HC
H2C
O
O
C
O
CH2
H2C
CH2
H2C
CH2
H2C
CH2
HC CH
CH2
H2C
CH2
H2C
CH2
H2C
CH2
CH3
C
O
CH2
H2C
CH2
H2C
CH2
H2C
CH2
HC CH
CH2
H2C
CH2
H2C
CH2
H2C
CH2
CH3
C
O
CH2
H2C
CH2
H2C
CH2
H2C
CH2
HC CH
CH2
H2C
CH2
H2C
CH2
H2C
CH2
CH3
HOO
C
CC
H
H
HO
H
O
OHH
CH2
HC
C
OH
C C
C
O
C
HOH
OH
H
CH2
CH2
H
HO
OH
Sucrose, sugar
Fat
Olestra
A
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From Olean ® WebsiteIn January 1996, the FDA approved the use of olestra in salty
snacks; Olean has been on the market since 1998 (Frito Lay and Pringles)
First FDA approved fat replacer that doesn’t “break down” at high temperatures
Hundreds of clinical tests have validated the safety of olestra
“One of the most studied food ingredients EVER.” “30 years of testing and research” ”Many medical doctors and culinary experts support the use of olestra-based products”
More than 3 billion servings (210 million lbs of chips or 70 million lbs of olestra) have been consumed by Americans.
A
www.olean.com (accessed October 2006)
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Theater Test• 1,092 people, aged 13-88, watched a movie and
ate up to 13 oz of chips (Olestra or TG)
• Median consumption of Olestra (60g vs 77 g) lower and taste lower (5.6 vs 6.4) on 9 point scale
• No difference in GI symptoms– TG 93 of 529 (17.6%)– Olestra 89 of 563 (15.8%)
• Funded by P&G
JAMA 1998, 279, 150-153.
A
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Center for Science in the Public Interest
• Procter & Gamble's own studies prove olestra causes diarrhea, cramps, and other symptoms.
• FDA has more than 20,000 complaints about olestra in its files--more than it has for all other food additives in history combined.
• “Olestra may cause loose stools and abdominal cramping” printed on package
A
www.cspinet.org/ (accessed October 2006)
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Vitamin Concerns
Procter & Gamble's eight-week clinical studies: – 8 gm/day (~16 olestra-containing potato chips) blood
serem carotenoids, alpha-carotene, beta-carotene, lutein, and lycopene levels were down by 50% to 60% by the end of the studies
– 32 gm/day of olestra reduced total serum levels by 70%
Vitamin K is really important: – Drug efficacy of anticoagulant Coumadin (1.5 million)
sensitive to fluctuations in vitamin K levels. – bone formation in fetal development and childhood and
retention of bone in older women linked to vitamin K
A
www.cspinet.org/ (accessed October 2006)
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Olestra’s Fate
• Sales of chips declined by 60%
• Approval not sought for other uses
• P&G sold the factory
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In the body, vitamin D is concentrated in the skin, liver, and kidneys. Vitamin A is found in the liver and kidneys and in membranes such as the mucus membranes and the retina of the eye. Excess vitamin A accumulates in the liver, and excess vitamin D in the kidneys.
What can you infer from these facts about the fat content of these tissues?
Question 3
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Why are deficiencies of vitamin D, E, and K rare, but deficiencies in vitamins C and B much more common?
Question 4
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How can we increase Vitamin absorption in the body?
• "In 1958, Roels and coworkers studied a group of Rwandan schoolboys who had low vitamin A levels in their blood. They divided the boys into three groups. One group ate 200g of carrots per day,[1] containing about 25 mg of beta-carotene, a compound that is equivalent to vitamin A in the body. A second group of boys received 20 mL of olive oil along with the same amount, 200g, of carrots. The third group of boys at no carrots but were given 28 mg beta-carotene dissolved directly in the olive oil."3
•[1] From Laursen, S; Mernitz, H. Would You Like Fries with That? The Fuss About Fats in our Diet; Wiley & Sons: New York , 2000. The study is from Roels, O. A.; Trout, M.; et. al. "Carotene Balances in Boys in Rwanda Where Vitamin A Deficincy is Prevalent," J Nutr. 1958, 65, 115-218.
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The following graph shows the blood plasma level of carotenes, the family of compounds related to beta-carotene, in micromoles carotene per liter of plasma vs. time.
Figure from: http://www.hsph.harvard.edu/Academics/nutr/olestra/fig6.html
What can you conclude from the graph?
0
2
4
6
8
10
12
Pla
sm
a C
aro
ten
es
(u
M)
0 5 12 19 26 31
Days of Dietary Supplement
Interaction of dietary beta-carotene and vegetable oil
200 gms carrots/day
carrots + 20 mL olive oil
28 mg beta-carotene + olive oil
Data from Roels, Trout, and Dejacquier, 1958
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Questions 5-65) Suggest some reasons why the beta-carotene dose
may have been more effective in raising blood plasma levels of carotene than the carrots, even when both were given with olive oil. Does that mean that beta-carotene supplements are better for you than carrots? Why or why not ?
6) Why do blood carotene levels seem to level out after a few days of dosage?
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Note
Similar experiments have shown that other carotenoids (plant-derived nutrients with chemical structures similar to carotene) are also absorbed better in the presence of oil. Other experiments show, moreover that the oil must be digestible. When indigestible (but safe to eat) mineral oil is given with the carotene, blood carotene levels do not rise.
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The Trio of Intermolecular Interactions
I. London Dispersion Forces– All molecules – Related to the polarizability of a molecule or
how distortable the molecule’s molecular orbital is.
– Larger = more easily distorted
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Question 7
Explain this trend: Boiling
point (oC)
CH4 -164
CH3CH3 -89
CH3CH2CH3 -42
C5H12 36
C6H14 69
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II. Dipole-dipole
Molecules that have dipoles interact
CCl
Cl
Cl
H
+CCl
Cl
Cl
H
+
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Question 8
Acetone and chlorine both have the same molecular weight. Acetone boils at about 58 °C, whereas chlorine boils at –34 °C. Explain why there is such a large difference in their boiling points.
Acetone has the following structure: O
CC
H
HH
CH
HH
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III. Hydrogen Bonding
• Especially strong dipole-dipole
• N-H, O-H, F-H
• Intermolecular (dashed lines)
H F+ -
H F+ -
H
F
+
-
H F+ -
Picture from: http://www.elmhurst.edu/~chm/vchembook/images/122hbondwater.JPEG
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Question 9
Hydrogen bonding can also occur between different kinds of molecules. For example, an ammonia (NH3) molecule and a water (H2O) molecule. Draw ammonia and water, and any hydrogen bonding that could occur between them.
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Reference Sources
Primary sources are, “original, first-hand documents” 1
Examples: journal articles; research reports
Secondary sources are, “works that interpret or analyze the content of the primary sources.”2
Examples: Reference books, text books, scholarly publications, encyclopedias
1 http://www.lib.umich.edu/ugl/classes/eval/
2 http://www.lib.umich.edu/ugl/guides/assist/assignments/primarysources.html
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Wikipedia• Dynamic• Current• Good overview or starting place• No peer review• Anyone can change anything
“As with any source, especially those of unknown authorship, you should be wary and independently verify the accuracy of Wikipedia information if possible”1
1http://en.wikipedia.org/wiki/Wikipedia:Citing_Wikipedia
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The Internet
• Useful for pointing to primary sources
• Evaluate each web page for its sources
• Use the library resources. These will point you to a variety of edited databases.
• http://searchtools.lib.umich.edu
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Exam
• 8:00 pm TONIGHT in CHEM 1400
• Ethics of exam taking
• Regrades (by Friday, October 13th)
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