Benzyl Benzoate

Take a moment and think about your morning routine, maybe you wake up shower, do your hair, makeup and before you leave spray on perfume. Have you ever taken a step back and looked at the ingredients in the products you’re using? If there were ingredients you weren’t aware of have you researched them to see their health impacts? I’m guessing the general consensus is no because why should we, if companies are selling them they must be safe to put on or in our body. I did exactly this with my Marc Jacobs perfume and found a chemical called benzyl benzoate.

Benzyl benzoate does occur naturally it can be isolated from a species of plant called polyalthia which is native to India.¹ In the cosmetic industry benzyl benzoate is synthesized. Benzyl benzoate isn’t very toxic the LD₅₀ is 1680mg/kg if taken orally or 4000mg/kg if applied on the skin.³ This compound isn’t only used in the cosmetic industry it is actually very common in the treatment of scabies as a topical ointment.³ Scabies is a skin infection that is caused by mite bites that leads to excessive itching. Benzyl benzoate works by killing the mite’s immune system.³

In the cosmetic industry benzyl benzoate is used as a fixative meaning it stabilizes the perfume chemically.⁴ There hasn’t been a lot of research into the health impacts on what can happen when you are applying things like perfume to your body every day, but there was one study done that found that there was a connection in perfume being applied to the chest region and an increase in growth of breast cancer cells.⁵ There hasn’t been enough research into this to make this a definitive correlation but it is something to think about.

The purpose of writing this was to get you thinking do you really know what’s in the products you’re using? Personally, I will continue to use Marc Jacobs perfume, I am now aware that benzyl benzoate is a relatively safe product to use but I will keep an eye to see if any more research goes into finding if there is a correlation between it and the increase in breast cancer cells.

References:

¹National Center for Biotechnology Information. PubChem Database. Benzyl benzoate, CID=2345, https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-benzoate (accessed on Jan. 27, 2020)

² Opgrande, J., Brown, E., Hesser, M., & Andrews, J. (2003). Benzoic Acid. Kirk-Othmer Encyclopedia Of Chemical Technology. doi: 10.1002/0471238961.0205142615160718.a02.pub2

³Benzyl benzoate - DrugBank. (2020). Retrieved 29 January 2020, from https://www.drugbank.ca/drugs/DB00676

⁴ National Center for Biotechnology Information. PubChem Database. Benzyl benzoate, CID=2345, https://pubchem.ncbi.nlm.nih.gov/compound/Benzyl-benzoate (accessed on Jan. 27, 2020)

⁵ Charles, A., & Darbre, P. (2009). Oestrogenic activity of benzyl salicylate, benzyl benzoate and butylphenylmethylpropional (Lilial) in MCF7 human breast cancer cellsin vitro. Journal Of Applied Toxicology, 29(5), 422-434. doi: 10.1002/jat.1429

Chemistry at Home- Ammonium Thiolactate

Figure 1. Hair with curlers 

Have you ever gone to the hair salon to get a perm and wondered what that strong meaty smell was? Well its a chemical called ammonium thiolactate. It is an organosulfide compound meaning it contains a thiol group which contains sulfur and usually an alkyl group which is what give it the smelly odor¹. It has the molecular formula C₃H₉NO₂S and has many other names it goes by¹.

It is often used in many different cosmetics such as hair dye, perm lotion and hair mousse as a reducing agent². What this means is that sulfur in the compound is giving electrons to an oxidizing agent in a redox reaction². It is also surprisingly used in flavoring of different types of food³. Now for the burning question, how does the chemical in a perm work? Well the reducing properties of the ammonium thiolactate open the cystine disulfide bonds of the keratin in the hair². The hair is then wrapped around hot rollers, where the heat penetrates the weakened hair and shapes it². Once the hair is shaped it an oxidizing agent such as hydrogen peroxide is used to return the cysteine disulfide bonds back together².

Ammonium thiolactate is not overly toxic after all it is used in food flavoring and in mice the lethal oral dose toxicity was found to be ≤1522mg/kg. Some of the health effects for those who are constantly working around the chemical are however at an increased health risk. These health risks include skin irritation which can lead to severe burns, eye irritation and respiratory tract irritation which can lead to bronchial infections if constantly being inhaled^4,5. However those who go to get their hair done every once in while are not likely to experience any of these concerns.

References:

(1) Ammoniumthiolactate.https://pubchem.ncbi.nlm.nih.gov/compound/Ammonium-thiolactate#section=Structures (accessed Jan 26, 2020).

(2) thiolactate, a.; 95%, A.; Thiolactate, A. The Good Scents Company - Aromatic/Hydrocarbon/Inorganic Ingredients Catalog information. http://www.thegoodscentscompany.com/data/rw1361541.html (accessed Feb 2, 2020).


(3) Thiolactic Acid by Penta Manufacturing Company - Food, Beverage & Nutrition. https://www.ulprospector.com/en/na/Food/Detail/16153/406125/Thiolactic-Acid (accessed Feb 4, 2020).


(4) http://152.91.79.3/publications/CAR/new/NA/NAFULLR/NA0700FR/NA721FR.pdf (accessed Jan 27, 2020).


(5) https://cloudfront.zoro.com/enhanced_pdf/ZQ_7nDhelo.PDF (accessed Feb 4, 2020).


Figure 1 source:https://www.pexels.com/photo/person-woman-hairstyle-macro-112782/ (accessed Feb.12, 2020). Creative Commons Zero- CC0

Is your turmeric milk latte just a money grab?

Turmeric is a spice that has grabbed a lot of press lately. Specifically you may have seen it on the coffee menu at your favourite hipster cafe, as a fancy, new, expensive latte ingredient. Sure it tastes pretty good, but is it really worth the extra money?

Figure 1. Turmeric milk latte

Turmeric’s history is lengthy, with mention of its medicinal use dating back almost 4000 years1. Turmeric was used in religious ceremonies, as a treatment for wound healing, and was often used to treat various digestive disorders all over Asia1. These days researchers are trying to unpack turmeric to figure out how it can be used in modern medicine, however, it’s not as easy as it looks. 

The active component of turmeric is called curcumin, and although the scientific community is still figuring this molecule out, thoughts are that it could be useful for things like:

• Anti-inflammation2
• Anti-microbial2
• Anti tumor2
• Antioxidant2

What scientists have discovered is that turmeric really struggles to get into the bloodstream if consumed orally3. In order to combat this problem researchers have developed specialized methods for increasing the bioavailability of curcumin3. Currently, the best method for getting the benefits of turmeric is to make the molecules incredibly small, called ‘nanoparticles’, or to cover it in a special fatty coating, called a lipophilic matrix3. Only then is it possible to see the active ingredient, curcumin, working its magic in the body. 

So the question remains; is the turmeric milk latte really worth the extra cash? The answer might lie with your choice on who you trust more. Do you trust ancient civilizations who have been using this spice throughout their history in the whole, unprocessed form? Or do you trust the scientists of today who believe that it’s full potential is lost until the spice has been made into tiny particles that your body can absorb? 

Personally, I believe that the whole spice must be active in your body to a certain degree, but I will probably stick to a regular latte and save a few dollars.

References

1Prasad, S.; Aggarwal, BB. Turmeric, the golden Spice: From Traditional Medicine to Modern Medicine. In: Benzie IFF, Wachtel-Galor S, editors. Herbal Medicine: Biomolecular and Clinical Aspects. 2nd edition. Boca Raton (FL): CRC Press/Taylor & Francis; 2011. Chapter 13. 

2National Center for Biotechnology Information. PubChem Database. Curcumin, CID=969516, https://pubchem.ncbi.nlm.nih.gov/compound/Curcumin (accessed on Jan. 22, 2020).

3Jager, R.; Lowery, R.; Calvanese, A.; Joy, J. Comparative absorption of curcumin formulations. Nutr J. 2014;13:11. Published 2014 Jan 24. doi:10.1186/1475-2891-13-11 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3918227/#__ffn_sectitle (accessed Jan 22, 2020).

Figure 1 Source: https://www.pxfuel.com/en/free-photo-qpxbl (accessed Feb 12, 2020). Creative Commons Zero - CC0

Chemistry at Home - Lidocaine by Ephraim Ng

Lidocaine is a chemical that is used as a local anesthetic and numbing agent¹. It is

commonly found at home in Polysporin® and pain relief patches. The lidocaine in

Polysporin® minimizes the amount of pain from cuts and scrapes². Lidocaine is also found at the dental office since it is used as a freezing agent during cavity fillings and oral surgeries³. With lidocaine being a commonly used household product, health and safety concerning this chemical is very important. The oral LD50 of lidocaine in mice is 292 mg/kg⁴. To put this into perspective, a 30 g tube of Polysporin® contains 1.5 grams of lidocaine. If we assume humans have an LD50 similar to mice, it would require eating 13 tubes of Polysporin® to have a 50% chance of killing a 70 kg human from lidocaine overdose. This isn’t the intended use for Polysporin®, if used properly, there is no way to receive such a high dose of lidocaine. Lidocaine is very safe if used for its intended purpose.  

Lidocaine’s structure is composed of mainly carbons and hydrogens and one each of

oxygen and nitrogen¹. The discovery of lidocaine dates back to the 1930s when a scientist

Euler-Cheplin isolated a compound from a mutant strain of barley named gramine⁵.

Euler-Chelpin’s colleague, Erdtman, was able to modify the arrangement in its chemical

structure and named this new compound isogramine⁵. Erdtman tasted this compound

and found that it made his tongue numb (don’t do this in the lab, it is super dangerous)⁵.

Knowing this, the scientists modified the structure of the chemical further and eventually

synthesized lidocaine which became the new standard for local anesthesia⁵. Mass lidocaine production is done by reacting small molecules together to form the larger lidocaine molecule⁶. 

There aren’t many controversies surrounding lidocaine but pain relief patches

shockingly don’t have any clinical evidence of being able to relieve arthritis related pain⁷.

Capsaicin creams and oral painkillers are better at relieving this kind of pain⁷. Lidocaine

is a very safe chemical; I would have no problems with my dentist using lidocaine and

will continue to use Polysporin®. You won’t catch me using the pain relief patches though.

1. Lidocaine. (n.d.). Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/Lidocaine#section=2D-Structure
2. Lidocaine - brand name list from Drugs.com.(n.d.). Retrieved from https://www.drugs.com/ingredient/lidocaine.html
3. Nordqvist, J. Uses, types, and risks of local anesthesia. (2017). https://www.medicalnewstoday.com/articles/265689.php#uses
4. ONeil, M. J., Heckelman, P. E., & Dobbelaar, P. H. (2013). The Merck index: an encyclopedia of chemicals, drugs, and biologicals. Cambridge, UK: Royal Society of Chemistry.
5. Gordh, T., Gordh, T. E., & Lindqvist, K. (2010). Lidocaine: The Origin of a Modern Local Anesthetic. Anesthesiology, 113(6), 1433–1437. doi: 10.1097/aln.0b013e3181fcef48
6. The synthesis of Lidocaine. (n.d.)  Retrieved from http://home.sandiego.edu/~khuong/chem302L/Handouts/Lidocaine_handout_Su07.pdf
7. Winter, G. (2018, October 2). The painful truth about lidocaine patches. Retrieved from https://www.irishtimes.com/life-and-style/health-family/the-painful-truth-about-lidocaine-patches-1.3640750

Chemistry at home - Triclosan 

"Antibacterial Soap Triclosan" by JeepersMedia is licensed under CC BY 2.0 

I hope this picture looks familiar to you as you should be using this stuff everyday. The thing you might not know is that most of the soaps you use contain triclosan. Along with other personal care items like deodorant, toothpaste, acne cream and body wash.^1,2 It also can be found in common household items like chopping boards, sports equipment and shoes.^1,2

Triclosan is an antimicrobial agent meaning it slows down the growth of bacteria. It is the most effective against gram positive bacteria, fungi and yeast. It is least effective against gram negative bacteria, microbacteria and viruses.³ It targets the bacteria by two ways, either by inhibiting fatty acid synthesis or by going inside the bacterial cell membranes to disrupt the cell.³ This is also the reason why it is added to toothpaste as it prevents gingivitis and is an effective anti-plaque agent.³

There are a few health concerns for humans and animals. The major concern for humans is it effects thyroid homeostasis.² It can be a mild eye and skin irritant in high doses over 9300mg/kg¹, this is its dermal toxicity number which is higher than we could absorb by using everyday personal care products. The biggest safety concern is for animals as triclosan has been found in high concentrations on surface waters. This causes algal speciation to decrease and it bioconcentrates in fish causing toxic levels.³

Currently in Canada triclosan is not banned but in the United Sates and part of Europe the FDA has banned certain soaps from being marketed.⁴ Triclosan is still in toothpaste and deodorant as it was proven to reduce bacteria count but the soaps tested did not kill more bacteria then normal soaps without triclosan. Therefore, there is natural alternatives that exist like Carvacrol. Carvacrol is like triclosan because it is also a phenol with antibacterial properties.⁵

^References 

(1)         Triclosan | C12H7Cl3O2 - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/5564#section=Absorption-Distribution-and-Excretion (accessed Jan 28, 2020).

(2)         Triclosan - DrugBank https://www.drugbank.ca/drugs/DB08604 (accessed Jan 28, 2020).

(3)         hand sanitizer -- Britannica Academic https://academic-eb-com.libproxy.mtroyal.ca/levels/collegiate/article/hand-sanitizer/623827 (accessed Feb 3, 2020).

(4)         5 Things to Know About Triclosan | FDA https://www.fda.gov/consumers/consumer-updates/5-things-know-about-triclosan (accessed Feb 3, 2020).

(5)         Carvacrol | C10H14O - PubChem https://pubchem.ncbi.nlm.nih.gov/compound/Carvacrol (accessed Feb 4, 2020).

Joshua Paredes Chemistry at home: Tylenol.

Tylenol, referred to scientifically as N-(4-hydroxyphenyl), is a very common painkiller that most individuals are aware of and have in their homes.1 The active component of tylenol is called acetaminophen, and that is the chemical in tylenol that is responsible for pain relief.1 Tylenol is known for its quick-acting pain relief and help in treating people with fevers and headaches, but scientists still do not know exactly how it works in the body.2 It is believed to be involved with preventing the release of chemicals in the brain that cause the sensation of pain, but how tylenol achieves this is still a mystery.2 

Unfortunately, tylenol is actually very toxic if too much is taken, and that may be a lot less than people think.3 It may be possible to take too much if you take other generic painkillers, where the active ingredient is also acetaminophen.4 The major consequence of tylenol overdose is liver failure from toxic liver disease.4 To put it in perspective, the cause of most (>50%) of all liver diseases in the united states is caused by tylenol overdosing.5 Fortunately, there is an antidote, called N-acetylcysteine that prevents the effects of overdosing by helping your liver create more chemicals that help get rid of the tylenol.2 

It’s not all bad news though. A lot of people are familiar and commonly use tylenol as their go-to painkiller at home, but there are a lot of alternatives that are less toxic to the body that you can use. These chemicals are called non-steroidal anti inflammatory drugs, which are a lot more common than you might think. Some of these drugs are: advil, aleve, midol, and motrin.4 Although there are also side effects that are associated with these drugs as well, the risk of developing these are lower than that of tylenol.4 

References

(1) PubChem. Acetaminophen, 2004. https://pubchem.ncbi.nlm.nih.gov/compound/Acetaminophen (accessed January 16, 2020).

(2) Jaeschke, H. Innate Immunity and Acetaminophen-Induced Liver Injury: Why so Many Controversies? Hepatology 2008, 48 (3), 699–701. https://doi.org/10.1002/hep.22556.

(3) McGill, M. R.; Jaeschke, H. Metabolism and Disposition of Acetaminophen: Recent Advances in Relation to Hepatotoxicity and Diagnosis. Pharm. Res. 2013, 30 (9), 2174–2187. https://doi.org/10.1007/s11095-013-1007-6.

(4) Tylenol vs Advil: What's the difference? https://www.drugs.com/medical-answers/tylenol-advil-difference-3126965/ (accessed Jan 28, 2020).

(5) Larson, A. M.; Polson, J.; Fontana, R. J.; Davern, T. J.; Lalani, E.; Hynan, L. S.; Reisch, J. S.; Schiødt, F. V.; Ostapowicz, G.; Shakil, A. O.; et al. Acetaminophen-Induced Acute Liver Failure: Results of a United States Multicenter, Prospective Study. Hepatology 2005, 42 (6), 1364–1372. https://doi.org/10.1002/hep.20948.