Omega-3 Acids Fight Cancer

Scientists at the University of Guelph have found that omega-3s from fish are better at preventing cancer than omega-3s from plants.

"Omega-3s" refer to omega-3 fatty acids which are a type of long-chain, polyunsaturated carboxylic  acid. Long-chain carboxylic acids are referred to as "fatty acids".
The three omega-3 fatty acids studied were: 

• α-linolenic acid (ALA) which is found in plant seeds and oils

• eicosapentaenoic acid (EPA) which is found in fish, algae and phytoplankton

• docosahexaenoic acid (DHA) which is found in fish, algae and phytoplankton

 The skeletal structural formula for α-linolenic acid is shown below:

 The IUPAC name of α-linolenic acid is (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid. 
The carbon atom of the carboxyl functional group (COOH) is labelled as 1, the next carbon atom in the chain is 2, then 3, etc, up until we reach the last carbon in the chain, carbon 18. The parent hydrocarbon for this molecule is therefore octadecane, with a suffix added for the carboxyl functional group, so we have octadecanoic acid. 
Along the way we find 3 (tri) double bonds (en) at carbons numbered 9, 12 and 15, so we modify the name of the carboxylic acid in one of two ways:

• 9,12,15-octadecatrienoic acid

• octadeca-9,12,15-trienoic acid

The "Z" indicates the 3-dimensional geometry,  in this case the "Z" geometry equates to a "cis" geometry.
So why would  (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid be called an omega-3 acid?
There is an alternative naming "system" (not IUPAC)  in which the first carbon atom is not labelled 1, but instead it is called "alpha" (α), and, the carbon atom at the end of the long hydrocarbon chain is called "omega" (ω). Then, the last carbon atom in the chain (omega) is labelled 1, and you start counting back towards the carboxyl functional group. If you do this, you will find that carbon 3 has a double on it, hence, (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid is called an omega-3 fatty acid. The 3 indicates the position of the first double bond from the omega carbon atom.

The skeletal structural formula of eicosapentaenoic acid is shown below:

The IUPAC name for this molecule is (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Icosapentaenoic acid. 
There are 20 carbon atoms in the chain so the parent hydrocarbon chain is icosane, which is modified with a suffix because there is a carboxyl functional group, icosanoic acid.
There are 5 (pent) double bonds (en) located on carbons 5, 8, 11, 14 and 17, so the name of this molecule is either:

• 5,8,11,14,17-icosapentenoic acid

• icosa-5,8,11,14,17-pentenoic acid

Once again, the Zs in the name refer to the geometry (same as a "cis" geometry in this case).
Notice that, in the alternative naming "system" in which the last carbon atom in the chain is labelled "omega" and then you count backwards from this, we see that the first double bond encountered is on carbon 3, so this molecule is also referred to as an omega-3 fatty acid.

The skeletal structural formula below is that of docosahexaenoic acid:

This molecule has the IUPAC name (4Z,7Z,10Z,13Z,16Z,19Z)-4,7,10,13,16,19-Docosahexaenoic acid. 22 carbon atoms in the chain (docosa), 6 (hexa) double bonds on carbons 4, 7, 10, 13, 16, 19 and a carboxyl functional group: 4,7,10,13,16,19-docosahexaenoic acid or docosa-4,7,10,13,16,19-hexenoic acid. Zs indicate geometry (same as "cis" in this case).
Using the alternative numbering system, the first double bond occurs of the third carbon atom from the omega carbon atom (last carbon in the chain) so it is also classified as an omega-3 fatty acid.

While all three of these omega-3 fatty acids were shown to be effective in reducing the size of tumours in mice, however, higher doses of the plant-based α-linolenic acid was required to deliver the same impact as the omega-3 fatty acids found in fish (icosapentaenoic acid and docosahexaenoic acid)



Reference:

Jiajie Liu, Salma A. Abdelmagid, Christopher J. Pinelli, Jennifer M. Monk, Danyelle M. Liddle, Lyn M. Hillyer, Barbora Hucik, Anjali Silva, Sanjeena Subedi, Geoffrey A. Wood, Lindsay E. Robinson, William J. Muller, David W.L. Ma. Marine fish oil is more potent than plant based n-3 polyunsaturated fatty acids in the prevention of mammary tumours. The Journal of Nutritional Biochemistry, 2017; DOI: 10.1016/j.jnutbio.2017.12.011

Further Reading:
Introduction to naming organic molecules: http://www.ausetute.com.au/namctut1.html
Introduction to functional groups: http://www.ausetute.com.au/fungroup.html
Fatty acids: http://www.ausetute.com.au/fattyacid.html 
Structure and properties of carboxylic acids: http://www.ausetute.com.au/carboxyl.html
Molecular formula: http://www.ausetute.com.au/molecularformula.html
2-Dimensional structural formula: http://www.ausetute.com.au/structural2D.html
Condensed structural formula: http://www.ausetute.com.au/condensedsf.html
Skeletal structural formula: http://www.ausetute.com.au/skeletal.html
Cis-trans isomers: http://www.ausetute.com.au/cistranso.html 


Suggested Study Questions:

1. What functional group is common to all fatty acids? 
2. Define the following terms as they are used in chemistry:
   • saturated
   • unsaturated
   • monounsaturated
   • polyunsaturated
3.  Give the molecular formula for each of the three omega-3 acids in the article
4. The structural formula given in the article are referred to as "skeletal". What does this mean in chemistry?
5. Draw a 2-dimensional (full display) structural formula for each of the omega-3 acids in the article.
6. On the structural formula of each of the three omega-3 acids circle the:
   
   • carboxyl functional group in red
   • double bonds in blue
7. What features are common to three omega-3 acids in the article?
8.  In what ways do the the three omega-3 acids in the article differ?
9. You have probable heard about omega-6 acids. How do you think an omega-6 acid will be similar to an omega-3 acid?
10. How will an omega-6 acid be different from an omega-3 acid?
11. What is meant by a cis isomer and a trans isomer?
12. All the omega-3 fatty acids in the article are the cis isomers. Build a model, and draw, a trans isomer of one of the fatty acids.

Nano-zinc oxide and the Environment

Increasingly, we are making use of nanoparticles because of their unique properties compared to the same substance in bulk material. Many cosmetics, including sunscreens and sunblocks, now contain nanoparticles. When you go swimming or wash, these nanoparticles are washed off. Depending on where the nanoparticles are washed off, the waste water may directly enter a natural water system such as a river or ocean, it may end up in sewerage sludge, and it may eventually end up on land. What scientists do not know is just how many nanoparticles are entering the earth, air and water.

It is estimated that carbon nanotubes, which form part of a composite material in objects such as bicycle frames and tennis rackets, can take 10 years to breakdown and be released into the environment. On the other hand, about half of the cosmetic nanoparticles enter our waste water within one year.

Europe currently produces about 39,000 tons of nano-titanium dioxide per year, and it is estimated that the concentration of these nanoparticles in effected areas is now 61 micrograms per kilogram of ground. For humans, the maximum "safe" levels for exposure to these nanoparticles is set at:

• 2,500 mg/kg/day for oral exposure
• 2.4 mg/m³ for inhalation

While small amounts of zinc oxide are beneficial to plant growth, larger amounts can impair seed germination. Plants take up the free zinc ions in aqueous solution rather than the zinc oxide particles. This zinc becomes incorporated into the plants we eat. Zinc is an essential element in the human diet. The recommended dietary allowance of zinc for men is 11 mg/day, and for women is 8 mg/day. There are concerns that the increasing level of zinc in  plants may lead to accumulation of zinc in humans which will be detrimental to our health. Ingesting more than about 100 mg of zinc per day may lead to chronic toxicity.

Research into the environmental impact of nanoparticles, and their impact on plant and animal health, will continue for a long time.

Reference:
https://www.sciencedaily.com/releases/2016/05/160512084646.htm

Further reading
Nanotechnology: http://www.ausetute.com.au/nanotech.html
Graphene and Fullerenes: http://www.ausetute.com.au/graphene.html
Solutions Concepts: http://www.ausetute.com.au/solutions.html
Weight percent (w/w): http://www.ausetute.com.au/weightpc.html
Parts per MIllion (ppm): http://www.ausetute.com.au/partspm.html

Suggested Study Questions:

1. What is meant by the term "nanoparticle"?
2. If a nanoparticle of zinc oxide has a diameter of 20 nm, what is its diameter in:
   • metres
   • centimetres
   • millimetres
   • micrometres
3. Give an example of one property of bulk zinc oxide that is different to nanoparticles of zinc oxide.
4. Explain why zinc oxide nanoparticles are used in sunscreens.
5. What is a carbon nanotube?
6. Why are carbon nanotubes used in the production of bicycle frames?
7. Why are concentrations of titanium dioxide nanoparticles in soil given in units of micorgrams per kilogram of soil rather than in moles per litre?
8. Convert the following concentrations into parts per million (ppm)
   • 2,500 mg kg^-1
   • 2.4 mg m^-3
9. Using the recommended dietary allowance figures in the article, determine the mass in grams of zinc allowed for a:
   • 58 kg woman each day
   • 79 kg man each day
10. A typical vitamin pill contains 25 mg of zinc. By consuming 1 tablet per day, will the man or woman above exceed the recommended daily allowance of zinc?
11. 6 raw oysters contain 32 mg of zinc. How many oysters can the man and woman above eat before exceeding the recommended dietary allowance of zinc?
12. 85 g of cooked beef contains 7 mg of zinc. What mass of beef can the man and woman above ingest before exceeding the recommended dietary allowance of zinc.
13. 28 g of dry roasted cashews contain 1.6 mg of zinc. What mass of zinc, in grams, is present in 750 g bag of cashews?
14. 1/2 cup of cooked red kidney beans contain 0.9 mg of zinc. How many cups of red kidney beans would our man and woman above need to consume in order to achieve their recomended dietary allowance of zinc?
15. Do you think you should take a daily vitamin pill containing zinc? Justify your answer.

Organic Chemicals in Smoker's Breath

The Chemistry Department of the University of Girona (UdG) has been investigating the chemicals present in the breath of smokers. They analysed some volatile organic compounds such as benzene, 2,5-dimethylfurane, toluene, o-xylene and p-xylene, which could be used as bio-indicators of the condition of a smoker, and have shown that only 2,5-dimethylfuran provides effective results for breath samples. 2,5-dimethylfuran can also be present in the breath of passive smokers if they have had direct contact with tobacco smoke over a prolonged period.

Benzene is only useful as a bio-indicator when tobacco consumption is relatively high and when testing takes place 1-2 hours after a smoking a cigarette.

Toluene and xylene levels are only significant for those who smoke a lot and when little time has passed since smoking the last cigarette.

Reference:
Monica Alonso, Mar Castellanos, Juan M. Sanchez. Evaluation of potential breath biomarkers for active smoking: assessment of smoking habits. Analytical and Bioanalytical Chemistry, 2010; 396 (8): 2987 DOI: 10.1007/s00216-010-3524-z