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The Truth About Grapefruit Seed Extract

February 17, 2010

Article Courtesy of: Chemical of the Day

Since my original post on Grapefruit Seed Extract, I’ve stumbled upon some new eye-opening information, so I thought I’d expand the subject here.

The big controversy that’s been going on for years with Grapefruit Seed Extract lies in its potential to be contaminated with benzalkonium chloride, parabens, and triclosan.  Numerous studies have tested samples of commercially produced GSE and found these contaminants to be present.  (See here, here, here and here.)  The biggest contaminant found is benzalkonium chloride, a chemical that rates a 7 in the cosmetics database that’s a known immune system toxin, skin toxin, and possible cancer risk.

Some studies have shown that without these contaminants, a truly natural extract of grapefruit seed and pulp in ethanol or glycerin, had no antibacterial properties.  However, GSE apologists claim that GSE can be effective without these contaminants.  So, what is the truth? Is there such thing as a “pure” GSE, and if so, is it effective?

Grapefruit Seed Extract was first developed in 1972 by a man by the name of Dr. Jacob Harich.  Today, there is one main manufacturer of GSE that defenders claim is pure.  It is sold under the name Citricidal. This website describes how it is made:

  1. Grapefruit pulp and seed is dried and ground into a fine powder.
  2. The powder is dissolved in purified water and distilled to remove the fiber and pectin.
  3. The distilled slurry is spray dried at low temperatures forming a concentrated flavonoid powder.
  4. This concentrated powder is dissolved in vegetable glycerine and heated.
  5. Food grade ammonium chloride and ascorbic acid are added, and this mixture is heated under pressure. The amount of ammonium chloride remaining in finished Citricidal is 15-19%; the amount of ascorbic acid remaining is 2.5-3.0%.
  6. The ammoniated mixture undergoes catalytic conversion using natural catalysts, including hydrochloric acid and natural enzymes. There is no residue of hydrochloric acid after the reaction.
  7. The slurry is cooled, filtered, and treated with ultraviolet light.

As you can see, this isn’t a truly natural process, it being treated with hydrochloric acid and ammonium chloride.  After all the chemical reactions occur, the final composition of the extract is made up of about 60% diphenol hydroxybenzene, a chemical classified as a quaternary ammonium chloride–the same as benzethonium chloride.  In fact, it is nearly chemically identical to benzethonium chloride. This is one possible reason that lab tests have shown GSE to be “contaminated” with benzethonium chloride–the equipment possibly misread the diphenol hydroxybenzene.

Typically, when a truly natural extract is made, plant matter is let to steep in a solvent such as water (as in making tea), in alcohol (like the vanilla extract you’d use in baking), or in glycerin (like with many herbal supplements you’d find at the health food stores) to extract the plant’s beneficial or desirable compounds, whether it be a flavor, smell, or antioxidant.  It’s a one or two step process that doesn’t involve other chemical processing.  GSE is clearly not a natural extract, but a synthetic ingredient, considering it goes through 7 steps of processing and the extract doesn’t retain the original compounds present in grapefruit.

Mountain Rose Herbs, one of the most respected and trusted suppliers of organic herbs, extracts, and essential oils lists the composition of the pure GSE they sell (which is most likely Citricidal brand):

Ascorbic Acid- 3%

Glycerol- 36%

Diphenol Hydroxybenzene (Quaternary compound from Grapefruit Bioflavinoid)- 58.5%

Heavy Metals- None detected

Benzethonium Chloride- None Detected

Methyl Hydroxybenzoate – None Detected

Propyl Hydroxybenzoate – None Detected

Triclosan- None Detected

So, while it is pure from other contaminants, it is primarily diphenol hydroxybenzene.  One fallacy I’ve found on discussion boards online have been that since it comes from Mountain Rose Herbs, it must be safe and organic.  You’ll notice that this ingredient is not classified as certified organic on their website.

When I first posted my Chemical of the Day on GSE, there were some comments written on the post.  I have to now revise my original replies with this new information in mind.

Sally Leachko founder Meaodwlake Farm wrote:

I applaud your efforts Stepahnie. However, you are only exposing your readers to a fraction of the information available about GSE and controversy that surrounds this ingredient. Is some GSE contaminated? It appears so. Is all? Absolutely not. Meadowlake Farm Honeybee Products uses organic GSE from one source and we’ve had it tested by an independent lab multiple times. Contrary to what you indicate it has some anti-microbial properties, that is why we use it as a part of our proprietary 100% natural preservation system.

I originally commended her efforts to make sure that her extract was pure.  However, even though her extract isn’t contaminated with other chemicals, knowing that “pure” GSE is composed of mainly diphenyl hydroxybenzene, I am forced to rescind my comments.  And while I’m sure that her motives are good (their company seems to work a lot towards sustainability and organic causes), I think that the industry is rife with misinformation, even from suppliers of chemicals to companies.

Another reader of my original post wrote:

If the ingredient is listed as Extracts of Organic Grapefruit Seed (certified organic by Soil Association Certification Limited) in a product would it be okay?

I originally thought, sure, it’s certified organic, it’s fine.  However, now I have more information and have to change my reply.

Right now, Citricidal is actually made from organic grapefruit.  But, whether it’s organic grapefruit or not, the extract is still going to contain diphenol hydroxybenzene.  But how did this company get a GSE that was certified organic, it being a synthetic chemical?  Well, notice that the certifying body isn’t the USDA, by the Soil Association.  The Soil Association is the European organic standard, and the requirements are much less strict than that of the USDA.  They will allow and certify a synthetic chemical like GSE if it meets certain criteria for biodegradability, aquatic toxicity and bioaccumulation.  So, since the grapefruits were organically grown, and it meets the requirements, they approve the extract as organic, even though it’s a synthetic chemical.  The Soil Association also approves phenoxyethanol as a preservative ingredient.  The USDA will not certify GSE, or allow it in a certified organic product.  If you see a USDA certified organic product with GSE, it is illegally labelled.  GSE is not on the USDA’s list of approved non-organic substances (they allow a few non-organic ingredients like vitamin E in to their products).

So, let’s take a look at diphenol hydroxybenzone.  Why exactly do we want to avoid it?

The makers of GSE states that it’s been extensively tested for toxicity and health effects and claim that it is safe.  However, all of these studies only tested the effects when it was taken internally.  When taken internally, chemicals have a chance to be metabolized and broken down by the body.  However, when applied topically, they can be absorbed in the skin and enter the bloodstream in their whole form.

The problem that I see with diphenol hydroxybenzene is the fact that on a molecular level, it’s full of benzene rings.  The name “diphenol” means that there are two phenol groups.  Phenol is a benzene ring with one hydrogen and one oxygen molecule.  Chemicals with benzene rings are particularly worrisome in personal care products because once they enter the bloodstream they can mimic the hormone estrogen.  [For a detailed explanation of this, check out my article on Japanese Honeysuckle Extract.]  Estrogen is primarily made up of benzene rings, and our estrogen receptors are made to “fit” benzene rings.  So, when a chemical with a benzene ring enters the body, it has the potential to lock up in the estrogen receptor and can stimulate it.

The strange thing with diphenol hydroxybenzene is that there are no chemical diagrams provided by the manufacturer (or anywhere, even in organic chemistry guides), and the name of the chemical doesn’t help (as it should) in finding its chemical structure.  Hydroxybenzene is just another name for phenol, so the name means “2 phenol phenol,” which is weird.  My guess is that it’s a simplified name for the chemical.  The manufacturer does say that hydroxybenzene is nearly identical to bezenthonium chloride, which looks like this:


The two hexagonal rings you see in the structure are the problematic benzene rings that I was talking about.  And indeed, this chemical has been shown to be an endocrine/reproductive disruptor by a 1995 RTEC study.  It also carries the risk of being a strong skin irritant, and it showed tumor formation at moderate doses.  (see the Cosmetics Database report) However, in its defense, according to National Toxicology Program studies, it exhibited no evidence of carcinogenity or endocrine disruption in a two-year rat and mouse study.  This study did, however, show that the animals treated with benzethonium chloride did have increased inflammation in the body and a slightly lower survival rate than the control group.

The bottom line is that while there is conflicting evidence of the other negative health effects of benzethonium chloride (and the diphenol hydroxybenzene present in GSE), at the very least it’s a skin irritant that increases inflammation in the body.  My personal opinion on it is that it is safer than other preservatives. However, if you prescribe to an organic mindset and lifestyle, you will want to avoid Grapefruit Seed Extract, for it is nothing other than a synthetic chemical.

Note: Grapefruit essential oil is natural, and not the same thing as Grapefruit Seed Extract.

14 Comments leave one →
  1. June 22, 2010 12:05 am

    Supraveni Chemicals manufactures plenty of chemical products like sodium sulphate, sulphuric acid, nitric acid, hydrochloric acid, barium sulphate & sodium hydroxide, for more details visit http://www.supravenichemicals.com/

  2. Nicole permalink
    September 1, 2010 12:57 pm

    Wow, thank you for such a complete article!

  3. November 16, 2010 10:58 pm

    health foods that are organice and have natural source should be the stuff that we should take -`:

  4. Dene Godfrey permalink
    December 9, 2010 8:06 am

    Sorry, but whilst you actually talk a lot of sense about the GSE situation, you are totally misinformed about the benzene ring! Compounds with a benzene ring do NOT automatically mimic oestrogen. Benzene rings are so common in natural chemicals they are in thousands of different compounds in our own bodies, and everywhere else throughout the natural world. The benzene ring is one of the fundamental building blocks of many/most natural substances. Even just neat benzene alone does not mimic oestrogen! I do not understand where you get this information from!

    • December 10, 2010 6:15 am

      Hey Dene!
      Thanks for your post- we didn’t write the article- if you have additional knowledge- please feel free to post links or information to the contrary! We welcome all input. Also- if you’d like to address the writer of the article- they are listed in the ‘by’ line at top of article. Thanks!

      • Dene Godfrey permalink
        December 10, 2010 7:18 am

        Thanks – I hadn’t really noticed that it wasn’t your article. I will also write to Stephanie with the same comments, but I think that it remains valid to post my comments here in the hope that your readers will take note. One more thing before I go – there is a very strong assumption in this post that “natural” means safe. It doesn’t, any more than “synthetic” means dangerous – a link for further reading if you are interested:

        http://personalcaretruth.com/2010/05/natural-is-safe-and-synthetic-is-dangerous-truth-is-safe-and-myths-are-dangerous/

        I hope you find it useful.

  5. December 10, 2010 11:28 pm

    Hi! This is Stephanie, the originator of this article. Thanks for helping us spread the word about this ingredient!

    Dene–I’ve responded to your comments on my original post, but I’ll post it here too:

    Of course, not everything with a benzene ring is estrogenic. Numerous beneficial antioxidants and compounds contain benzene rings. Many of the building blocks of life are built of benzene rings.

    Estradiol is one of those building blocks. The most active end of the estradiol molecule is the end with the benzene ring. Our estrogen receptors are built to fit this benzene ring, so when molecules with a single benzene ring on an end enters our bodies, it has the possibility to enter these estrogen receptors and thus stimulate the receptor molecule (thus acting estrogenically.)

    There is much evidence that benzene acts estrogenically.

    This study found that women exposed to benzene developed irregular menstrual cycles: http://www.ncbi.nlm.nih.gov/pubmed/11025497

    As did this study:
    http://www.ncbi.nlm.nih.gov/pubmed/11411330

    And this study found increased risk of breast cancer when exposed to benzene:
    http://www.ncbi.nlm.nih.gov/pubmed/19366049

    It is well-known that polyaromatic hydrocarbons (benzene-based compounds) act estrogenically. Look at all of the known estrogen mimickers…parabens, phthalates, bisphenol A…they all have benzene rings at the end of the molecular structure. All estrogen mimickers have benzene rings or something very similar in shape.

    If there were no evidence that GSE acted estrogenically, I wouldn’t indicate it as such entirely based on the molecular structure. But there IS evidence of its estrogenic nature, and my point of bringing up the benzene rings is because it is that particular end of the molecule that is likely to be the culprit.

  6. Dene Godfrey permalink
    February 13, 2011 4:43 am

    Hi Stephanie – just out of interest, can you share with me the original source of the quote that mentions diphenol hydroxybenzene with regards to GSE? I ask, because it sounds an unlikely chemical name. Hydroxybenzene IS phenol (as you say in the article), and prefixing a name with diphenol is not the usual chemical nomenclature – it would be diphenyl. Interestingly, when this term is Googled, virtually all the 239 hits are for your article, or articles referencing your article! I think the actual substance must be 2,6-diphenylphenol (CAS no. 2432-11-3), and I can find no reference to oestrogenic effects from this compound.
    Some of your terminology is incorrect – phenol is not a benzene ring with one hydrogen and one oxygen molecule. A molecule of hydrogen is 2 hydrogen atoms combined, and the same is the case for a molecule of oxygen. Phenol is a benzene ring with a hydroxyl group (OH) – atoms of the two elements, not molecules. This does not indicate even a basic grasp of chemistry, as this is a very fundamental point. Moreover, your comment that “diphenol means that there are two phenol groups is not true”, mainly because the correct nomenclature is “diphenyl”, and there is only one hydroxyl group in diphenylphenol. “2 phenol phenol” is another error. There is no such thing. The use of the “2″ indicates the structural position, not the number of groups. The number of groups is indicated by the use of prefixes, such as di-, tri-, etc. 2-phenylphenol exists – again, your knowledge of chemistry is not sufficient to be aware of these facts. You are unable to distinguish between phenol and phenyl – only one letter, but very different chemically.
    I have commented previously in other fora on your lack of chemistry – this is an important issue, because you are discussing highly technical points, but without sufficient knowledge to understand completely, thereby leading to disinformation being spread. Your persisant association of the benzene ring with oestrogen mimickry is misguided. It is not the only criteria for oestrogen mimickry, and not all oestrogen mimics contain benzene rings. The presence of a benzene ring in a structure means nothing without actual evidence from testing.

  7. Karin permalink
    May 21, 2011 12:53 pm

    I agree with Dene Godfrey. You obviously have no education in chemistry. Yes, GSE has benzene rings in its chemical structure, but that is not such a large concern. Many of the herbs and spices we use to cook with and drink as teas have chemical compounds with benzene rings in them. It is what makes them aromatic! Two such spices are ginger and cinnamon. Ginger has zingerone, shogaol, and gingerol. Cinnamon has cinnamaldehyde, eugenol, and anethole. All of these molecules have at least one benzene ring in them near the end of the molecule and these spices are safe to consume without worry of estrogenic effects.
    As for the articles you cite for your evidence, they are poor, at best. The benzene the cohort groups of women that were studied were very small (one had only 797 women!) and the benzene that they were exposed to was petrochemical in nature. One of the studies was started in 1950 and, since then, study protocol has changed to make improvements in the collection of data.

  8. Rickety Rack permalink
    November 15, 2011 1:45 pm

    Go ahead and avoid Citricidal if you want to be a purist, and maybe miss out on something that works better than anything else for what ails you, at very low toxicity. As for me, I just had 8 days straight of constant terrible diarrhea that was only getting worse clear up in a single day, in fact I felt better within an hours of using it. Since I probably had Giardiasis from handing leaf mulch with sick dog poop in it, the “standard” medical treatments were a nightmare to contemplate both for their ineffectiveness and their side effects. So yeah, keep preaching or implying the “wisdom” of “organic” purism , personally I’d stick to a wider-scope intelligence for my misery-preventing choices. Cripes I’m thankful Citricidal is available man the cost was trivial and the convenience (my local Vitamin Shoppe) was very nice too.

  9. Rickety Rack permalink
    November 15, 2011 1:51 pm

    Do follow through with organic virgin coconut oil, though! Anti-inflam, boost immunity, keep killin’ those pesky bad critters of all kinds. ;0)

  10. January 5, 2012 1:29 am

    somu organo-chem manufactures and exports 1,3 – CYCLOHEXANEDIONE /CAS NO.[504-02-9] an intermediate for preparation of Carvedilol, Ondansetron. An intermediate for preparation of Plant Growth Regulators and Herbicides.Dihydroresorcinol, Cyclohexane 1,3 dione, Carvedilol, Ondansetron, Plant growth regulators, Herbicides, Mesotrione, Sulcotrione in Corn, Wheat, Soyabean, Crop protection.

  11. Veronica permalink
    February 28, 2012 7:26 am

    Hello,
    I have just read an article about using GRAPEFRUIT SEED EXTRACT for candida yeast treatment and I really wanted to try. However after reading your article I’m not very sure any more… I found a liquid form of grapefruit seed extract where the ingredients are “Organic Grapefruit Seed Extract (Citrus paridisi), Organic Vegetable Glycerine” from Akamuti website. Do you know anything about that company, can I trust them?
    Thank you very much,
    Veronica

  12. Anna permalink
    May 5, 2012 3:16 pm

    I suggest EVERYONE reading this should do their own research instead of depending on one source for information. Although this article may have good intentions, I highly suggest to be skeptical of what you read. The writer made a simple mistake as classifying vegetable glycerin as a substance that can be used to extract preperties from herbs, this is VERY wrong. Alcohol is used in all tinctures, some companies will remove the acohol and later replace it with glycerin. If the writer made such a basic mistake, i wonder what else he/she is wrong about? Think about it.

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