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Here we explore some of the myths & legends!

Monday
Nov092009

A Chemist Takes Stephanie to Task on Phenoxyethanol

Recently one of our Chemical of the Day articles was featured in Utah Stories Magazine as a "Chemical of the Month" feature.  After a local chemist read the article, he challenged Stephanie's stance on phenoxyethanol and wrote in to the magazine.

I have just yesterday become acquainted with Utah Stories - what a great idea! In harmony with your stated objective of telling the undistorted truth, I'd like to make a few comments about one of the articles in your October 2009 edition. As a professional chemist, the article "Chemical of the Month," discussing a cosmetic additive called phenoxyethanol is a near-perfect example of distorting the truth to fit a pre-conceived idea.

The author's very first paragraph points out that phenoxyethanol is made from phenol, which itself is made from benzene, a known carcinogen. Phenol is then treated with ethylene oxide, another known carcinogen, then with an alkali. She is technically correct, but it makes as much sense to describe a very common compound around the house as being made from the reaction of a poison gas used in World War I with a substance that spontaneously bursts into flame if it comes in contact with air. That common substance is of course sodium chloride - table salt. That phenoxyethanol is made from rather scary ingredients does NOT necessarily mean that the material itself shares any of the adverse properties of its constituents, any more than table salt is a poisonous gas.

She also gives the following: "EWG Risk Score: 4" without defining where the EWG Risk Score comes from or what it means. It turns out that the Environmental Working Group is a non-profit organization that searches available databases of ingredients in cosmetics to determine the risks associated with each ingredient. The results of that search are published on line, and also used to lobby Congress to pass legislation making cosmetics safer. A look at the actual EWG report (see here) on phenoxyethanol is most enlightening. Note that the EWG is very careful to define the differences between the ingredient itself and the products in which it is used. Here is their statement:

Research studies have found that exposure to this ingredient -- not the products containing it -- caused the indicated health effect(s) in the studies reviewed by Skin Deep researchers. Actual health risks, if any, will vary based on the level of exposure to the ingredient and individual susceptibility -- information not available in Skin Deep.

The author of your article states that phenoxyethanol's use is limited in Japan, but somehow does not mention what the EWG documents: the chemical's use is restricted to cosmetics - the very area in which the material is generally used in the US. What a surprise!

By the way, EWG defines their risk score of 4 (on a 1-10 scale) as meaning "moderate hazard." Now remember that the score is for the chemical itself in its most concentrated form, not for products using that chemical. Since toxicity correlates to dosage, using such a material at the very low levels common for preservatives (phenoxyethanol's function in cosmetics) means that the actual risks presented by this material are very, very low.

The author's obvious goal in her article is to tout her 'chemical-free' product line. Yes, phenoxyethanol is a chemical, no doubt about it. But it's a far more benign material than one would think if your only information came from Stephanie Greenwood! If she wants to sell a truly synthetic-chemical-free product line, she will have to quit using virtually all commercially-available fragrances, eschew purchasing glycerine, and go back to lard, olive oil, fireplace ashes, and herbs to make her soaps, creams, and potions.

Now, it's clear that there are some very dangerous synthetic chemicals around, and that prudence demands caution - but to insist that we go back to the 17th century technologically in order to escape all those terrible materials is not only silly but unnecessary. If you would be interested, I would be pleased to write a short article on some of the fallacies inherent in so-called 'chemical-free' materials.

Finally, I'd like to point out that I'm not an industry shill: my company, GreenFire Energy, is engaged in production of energy using advanced geothermal techniques, including a novel process that creates energy while at the same time sequestering CO2! Life is fun--and good technology is good for our planet and all of us who live on it.

Yours,

Alan D. Eastman, PhD
Vice-President, Technical Development
GreenFire Energy
5698 Park Place East
Salt Lake City, UT 84121
http://www.greenfireenergy.com/

Stephanie's Rebuttal 

 

Dear Alan,

Well, it looks like I've succeeded--I live to stir up a good debate about chemicals!

Thank you so much for offering your perspective on phenoxyethanol. I think it's wonderful that you've challenged my perspective in a thoughtful manner. First I have to say that I'm not an employee or paid by Utah Stories, so my opinion does not necessarily reflect that of the publication. Chemical of the Day is a blog that I run, and due to the popularity of a previously published excerpt, Utah Stories asked me to offer one of my chemicals to their readers as a Chemical of the Month. And while I carefully research my information and believe everything to be true, Chemical of the Month is more of an opinion piece than the other hard-hitting journalism found in the publication. We will make this more clear for future pieces. That said, I'll be happy to delve deeper in substantiating my claims against the chemical. I hold fast to my claims.

Your point about table salt is not lost on me. I'm assuming you're talking about the classic textbook reaction of hydrochloric acid (the poisonous gas) and sodium hydroxide (the substance that can burst in to flame). However, on a chemical level, it's not a fully accurate analogy. HCl plus NaOH is a simple reaction dealing with only four elements. When measured precisely, we know that these two chemicals will combine to solely create water (H2O) and NaCl (table salt). This is simple inorganic chemistry. All original bonds are broken and reformed to create new compounds.

The creation of phenoxyethanol is a much more complex process involving more than one chemical reaction. Not all of the chemical bonds of the original compounds are broken down and re-formed as in your table salt analogy. (For our non-chemist readers I'm going to offer some explanations). Phenoxyethanol starts out as phenol. Phenol is an aromatic hydrocarbon, meaning that it contains a benzene ring. A benzene ring is basically a chemical ring made out of carbon and hydrogen. The chemical benzene is a simple ring of six hydrogen atoms and six carbon atoms hooked together in a hexagon style shape like this:

Benzene is a  known carcinogen.

 

 

 

 

Phenol is created when you take a benzene ring and substitute one of the hydrogen atoms with a hydroxyl group (an oxygen and a hydrogen):

Phenol
 

As you can see, it still retains the hexagon structure of the benzene ring. When a compound contains a benzene ring, it's called an "aromatic hydrocarbon." Because it is only one atom away from benzene, phenol still has many negative health effects. According to the World Health Organization, phenol "may cause effects on the central nervous system, heart and kidneys, resulting in convulsions, coma, cardiac disorders respiratory failure, collapse." It's also classified as a suspected carcinogen.

So, to make phenoxyethanol, you take phenol and you add ethylene oxide and an alkali. This reaction doesn't break down the benzene ring of the phenol, but just adds a longer "tail" to the structure.

Phenoxyethanol

Phenoxyethanol too is an aromatic hydrocarbon containing a benzene ring. In very simplified terms, this heavy tail makes phenoxyethanol less reactive than phenol or benzene, however it is still problematic. When ingested, phenoxyethanol is broken down in to glycolic acid, which is then broken down in to oxalic acid, which is toxic. In fact, the FDA recently recalled a nipple cream containing phenoxyethanol because of its toxic effects stating that phenoxyethanol can "depress the central nervous system and may cause vomiting and diarrhea, which can lead to dehydration in infants."

But the risk isn't limited to infants. Any time you have a benzene ring in a synthetic compound like this one, you have the risk of disrupting reproductive health. All three forms of estrogen (estrone, estradiol, and estriol) are made up of complex benzene rings. Estrogen receptors in the body are designed to react to these particular benzene rings. But when a synthetic chemical containing benzene rings enters the body, it binds to estrogen receptors and stimulates cells incorrectly or disrupts the biometabolic pathways. Each variation is going to interfere in different ways, some more strongly than others. Phenoxyethanol has been studied and it has been found to affect reproductive health (see here).

Getting back to the table salt analogy, I have one more point to make. Yes, theoretically, if you do combine hydrochloric acid with lye, you do get table salt. However, this probably isn't table salt you'd want to eat. The measurements and concentration of the two chemicals would have to be quite precise, otherwise you'd end up with salt contaminated with acid or lye. The same thing is true with phenoxyethanol. When you have phenol being treated with ethylene oxide, there is the risk that the end product is contaminated with ethylene oxide. In fact, many cosmetic ingredients are tainted with ethylene oxide (and subsequent byproduct, 1,4-dioxane).

One may argue that the exposure to phenoxyethanol and (subsequent dioxane contamination) is too small in cosmetic applications to affect health. You may say that you'd have to ingest gallons of the stuff to see the negative effects. Yes, perhaps using a lotion with a small amount of phenoxyethanol one time isn't going to make your body go haywire. But with cosmetic items we're looking at repeated multiple daily exposure. From the lotions, perfumes, makeups, deodorants, soaps, aftershaves, hairsprays, shampoos, conditioners, and other personal care items, we're exposing ourselves to gallons and gallons of chemicals every day, after day, after day. Not to mention the plastics around us like PVC, BPA and phlalates that are suspected to mimic estrogen, as well as pesticide residues from our foods. Perhaps isolated, exposing oneself to one chemical may not have terrible side effects. But over time these trace amounts do enter our bodies and do affect our health. If we can limit the toxic load that we're exposing ourselves to, why wouldn't we? For the most part, I do come from a "17th century" mindset. I don't use commercially-produced fragrances because most of them are aromatic hydrocarbons. I don't use synthetic preservatives or emulsifiers. I do, for the large majority, only use natural and organic herbs and oils in my products. The closer I am to making something the old-fashioned way, the better.

Perhaps my article was one-sided. But I feel it's not inappropriate. Billions of marketing dollars are spent every year by multi-national corporations to argue otherwise.

Perhaps my article was oversimplified. I simply did not have the room in a one page article to get down to the molecular level in an explanation, nor do most readers want a lesson in organic chemistry. So, I've written my blog and this article in an easy-to-digest format for readers' easy reference.

I apologize for not explaining what the EWG Risk Score was. This was an excerpt from my blog, and my blog readers are already familiar with the resource and look to this resource as a baseline for making decisions. I'll correct this for any future articles.

Alan, I applaud your efforts at GreenFire Energies. I am for technologies that clean our world and make it a better place. I would welcome an article explaining the fallacies of "chemical-free" products, as most of them that claim to be "natural" or "organic" still contain synthetic chemicals.

Sincerely,

Stephanie Greenwood

 

Tuesday
Jun162009

How about Rosemary?

Recently I received a call from a customer telling me that I should stop using rosemary extract in our shower gels because it was an estrogen mimicker. Of course this caught my ear as I started this company to get away from estrogen mimicking chemicals! I've done my research and have not heard anything about rosemary being an estrogen mimicker, so I asked the customer where she had heard this. She told me of a doctor who was selling her progesterone cream, and in his book he states that rosemary is estrogenic. I told her that I would consider reformulating the products if this was true (I'm not so stubborn that I won't listen to feedback!) She said she would e-mail me some information from this doctor.

So, of course, being the research-phile that I am, I started looking in to the possible estrogenic properties of rosemary. The first thing I noticed was that there were plenty of credible-looking websites that said rosemary was estrogenic, but none of them cited their sources. Not a single one cited a scientific study or journal that could back up the claim. It seems as if someone published it on a website somewhere and that information got cut and pasted to sites all over without researching the claim.

I did find some interesting things about rosemary, and how one of its active components, carnosic acid actually supports the liver in breaking down estrogen. (more below on the subject)

A couple days later, I heard back from my customer who had heard from the doctor. Here is what he wrote:

http://www.google.com/search?hl=en&safe=off&client=firefox-a&channel=s&rls=org.mozilla%3Aen-US%3Aofficial&hs=DuI&q=rosemary+abortifacient&btnG=Search

Rosemary acts as an abortifacient. Anything that is an abortifacient is antiprogesterone.

-*******, MD

A link to a google search wasn't particularly what I was looking for...a few minutes later he sent another e-mail:

Rosemary is very estrogenic. Even Phenol is estrogenic. The benzene rings are aromatic. Thus, any herb that is fragrant is suspect.

-*******, MD


So, I spent some time researching (not just googling, but actual research) and here is my rebuttal to him:

Thanks so much for considering my question. More so than a Google search, I'm looking for the scientific evidence of rosemary's estrogenic/abortive properties. Do you have any links to scientific or medical journals or studies on which you're basing your information? As this is a very personal concern (I too have suffered from estrogen dominance and was able to beat it through natural means and the suggestions of Dr. Lee) and I have put a lot of time and research in to this matter and into creating my line of products. It would be a great expense for me, but I will consider switching to vitamin E instead of rosemary extract as an antioxidant in my products if there is evidence of it being estrogenic.


That being said--I have not been able to find any evidence of rosemary’s estrogenic activity. On the contrary, the evidence that I have found would suggest that rosemary is anti-estrogen. Rosemary extract is high in carnosic acid , which aids the liver in breaking down estrogen (source). In fact, it's suggested to avoid rosemary if one is taking estrogen because it can break it down and counteract the effects of estrogen. The only fragment of evidence that would suggest rosemary as an abortifacient is this study that suggested that the ingestion of large amounts of rosemarinic acid led to the production of prostaglandin E2, high levels of which can induce labor. However, another study of rosemarinic acid applied topically reduced prostaglandin E2 levels as well as leukotriene B4 (and thus inflammation) and reduced the tumor (source). So there is conflicting evidence on the effects of rosmarinic acid on prostaglandin levels. What we do know is that rosemary is a powerful anti-oxidant that scavenges free radicals and even shows promise as an anti-cancer treatment, even for breast cancer (source) (source).

Regarding the benzene rings, here are the constituents of rosemary extract and rosemary essential oil.

Rosemary oil:

Cineole (terpenoid), Pinene (terpenoid), Borneol (terpene), Linalol (terpene), Alpha-Terpineol (terpene), Terpinen-4-ol (terpene), Bornyl Acetate (ester), Camphor (terpenoid), Thujone (ketone and monoterpene), Camphene (terpene), Limonene (terpene), Beta-Caryophyllen (terpene)

Rosemary Extract (Oleoresin)

1,8-cineole, (terpenoid) acetic acid (vinegar), camphor (terpenoid), carnosol, carvacrol (terpenoid), carvone (terpenoid), caryophyllene (terpene), chlorogenic acid (antioxidant ester), geraniol (terpenoid), hesperidin (flavonoid), limonene (terpene), luteolin (flavanoid), rosmarinic acid (polyphenol antioxidant), salicylates.

The chemicals here are primarily terpenes, terpenoids, flavanoids, and esters. None of these are aldehydes or contain benzene rings as you suggested. Although terpenes do have higher unsaturation indexes than many aliphatic compounds like benzenoid compounds, they are not, in the chemical sense, classified as aromatic compounds as you suggested.

I am very passionate about this subject and any thoughts or information on the matter would be greatly appreciated.

So, that's where I'm at now...I'm interested to see what the doctor comes back to me with...will he actually provide scientific evidence, or just another internet rumor?  I guess we'll see!  I'll keep you posted.

 

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