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Toxic lubes ?

Dear Reader,

As I suspect that most of my readers will understand how and when they have sex and with who is a very personal matter. Now it has come to my attention that Gwyneth Paltrow has been condemning the use of “lube” as her naturopathic doctor told her that “lube” is dangerous. Now I would like for the record to point out that I do not work for the “Drug Industry” and have no other vested interest in the “Drug Industry“. Nor do I work in the “lube industry” or get any money from them.

Maggie Ney her doctor had condemned “lubes” such as KY gel because they contain parabens, she claimed that

Parabens have actually been found inside breast tumor cells. And while we cannot conclude that parabens cause breast cancer, we can certainly argue that our bodies do not efficiently metabolize and eliminate it from our bodies. So when the FDA (which does not even regulate what goes into our lubricants) claims that the amounts of parabens are too low to pose a toxic effect in the body, they may be correct if we’re talking about a single exposure. The problems is, parabens are in our moisturizers, makeup, shaving creams, and facial cleansers. With multiple, daily use of these products, parabens and other chemicals are accumulating in our bodies, being passed onto our children, and playing a significant role in the health of our reproductive system.

Lets consider the ideas in this paragraph, we will start with the orange text. Now if I was to take a cancer cell regardless if it was lung, skin, liver or breast it would contain water. Maggie claims parabens have been found in breast cancer cells and then suggests that these substances could be responsible for the cancer. This might be an attempt to confuse the reader.

To my mind with the general public, they are almost always going to misunderstand the letter of the text as meaning “parabens can cause cancer”. I would say that a responsible doctor or medical scientist should take care to avoid leading the reader down a wrong path.

The great problem with cancer is that it originates in a single cell, this mutant cell keeps on dividing so it will be impossible to find this cell in a person who has clinical symptoms of cancer. So the substances in the cell at the moment it is removed from a person as part of a sample of a tumor will not be the substances present in the cell when it turned into a cancer cell. Also she has failed to show that the parabens were responsible for the cancer. Her link between the presence of parabens in cancer cells and the suggestion that they were part of the carcinogenic (cancer forming) process is on the same level as a person claiming that the water in cancer cells was responsible for the origin of the cancer.

One of the problems with the paper in 2004 in which P.D. Darbre, A. Aljarrah, W.R. Miller, N.G. Coldham, M.J. Sauer and G.S. Pope reported the concentrations of paraben esters in breast cancer tumors (Journal of Applied Toxicology, 2004, 24(1), 5-13) was that they failed to give any data for normal healthy breast tissue. This was pointed out by the editors of the journal. So already the significance of the finding of parabens in breast cancer samples has been called into doubt. This weakness in the paper which is a key part of Maggie’s argument is something which we should also consider when deciding what sort of under arm sprays to use or lubes to smear on our bodies.

For those of you who want to see what methyl paraben looks like then here is a diagram of the molecule.

Methyl paraben, methyl 4-hydroxybenzoate

Methyl paraben, methyl 4-hydroxybenzoate

Those of you who want to see the shape of the molecule through the miracle of x-ray crystallography should consult D. Vujovic and L.R. Nassimbeni, Cryst.Growth Des. , 2006, 6, 1595.

Next my English grammar expert points out that the use of the “and” I highlighted in red, is an example of rather bad written english. But we will not be making this post an english language lesson.

Next we look at the statement in blue, now this is an example of poor writing. Firstly the text is too informal and poorly defined. The text So when the FDA (which does not even regulate what goes into our lubricants) can be understood in several different ways.

Firstly I was to make a “lube” and market it only in Sweden then the FDA would not regulate it at all, so it would be correct for me to write “The FDA does not regulate my lube”. Equally if someone was to buy a lube which was made and marketed in Denmark and use it on holiday in France then they could quite correctly write “The FDA does not regulate my lube”. Instead of a single person writing (or talking) we were to have a group of people expressing an opinion then they could write (or say) under those conditions

“The FDA does not regulate our lube”

An alternative and meaning which could be understood from the text is the claim that the “FDA does not regulate what substances are used in lube”. I think that as a “doctor” that Maggie should be very careful with the way in which she writes and speaks. She should aim to avoid speaking in an ambigous manner, I would advise her for many reasons to make sure she writes clearly. But then when I looked at the FDA web site and made a search there for “sexual lubricant” then I found this group of documents bundled together into a single pdf. This is one of many such collections of documents, I do not want to endorse any particular brand and this is given as an example of some letters which have gone between companies which wish to market lube and the FDA.

After reading the documents in the pdf I have given a link to, I came to the conclusion that the FDA does regulate the marketing of “lube”. Part of this regulatory process includes a consideration of what is added to the lube. Keep in mind that multiple licenses are required for a drug to be brought to the market and sold or issued to people.

Consider for a moment as an example an asthma inhaler, now I am sure that some of my readers will be aware that cold air, infections, exposure to allergens, running, chopping wood, vigorous dancing or even sex can trigger breathing trouble in people who have asthma.

The drug must be shown to be safe and effective before a license is issued for the drug to be allowed as a treatment for a condition. For example salbutamol has been shown to be a safe and effective drug.

The drug must be made by a company which has a series of licenses (GMP etc etc) to be able to make pharma grade batches of the chemical which is intended to be used as the drug. The drug has to be made under special clean conditions, rather than being made under “normal” conditions.

The device which delivers the drug to the person taking it needs to have a license before it can be put on the market. Questions such as how well does it manage to deliver the same dose each time to the user need to be considered. Also how much of the drug is delivered to the lungs and how much is lost in the mouth could be an important issue with an asthma inhaler.

I see the same thing with the marketing of a “lube”, the substances in it must be ones which are regarded as “safe” in their intended use. Also the product must be able to deliver the substance in a safe way, issues such as microbiology need to be considered.

Next we will look at her statement in green, this is on the subject of how long these will stay in our bodies. I have already sent an email to Maggie Ney via the comments form on the website of her medical practice regarding the biological half lifes of the parabens. So far she has failed to reply. It so happens that two papers have been published in which the safety case for human exposure to two paraben esters have been reviewed. For methyl paraben, M.G. Soni, S.L. Taylor, N.A. Greenberg and G.A. Burdock wrote a paper entitled “Evaluation of the health aspects of methyl paraben: a review of the published literature”, (Food and Chemical Toxicology, 2002, 40(issue 10), pages 1335-1373) was the review on the substance. The abstract of the review contained the important phrase methyl paraben “is hydrolyzed to p-hydroxybenzoic acid, conjugated, and the conjugates are rapidly excreted in the urine. There is no evidence of accumulation.”

For those of you who might wounder what a paraben is, then it is an ester of 4-hydroxybenzoic acid. This is a carboxylic acid which is found in a range of fruits as a natural product. For example it was detected in coconuts by G. Dey, A. Sachan, S. Ghosh and A. Mitra, Industrial Crops and Products, 2003, 18(2),  pages 171-176. While in currants this carboxylic acid was found by K. Maatta, A. Kamal-Eldin and R. Torronen, Antioxidants & Redox Signaling, 2001, 3(6), 981-993. It gets even better, methyl paraben has been isolated from countless plants, reports of its isolation as a natural product go back into the 1960s.

While for propyl paraben the same authors reported very similar results in their survey of the literature in Food and Chemical Toxicology, 2001, 39(issue 6), pages 513-532.

I hold the view that if Maggie wants to continue to make these claims about parabens she should provide some evidence to show how M.G. Soni et. al. are wrong, her personal view that parabens are harmful is far less important than a pair of reviews which each cite over 100 papers. We should be striving towards evidence based medicine, here I see a conflict between Maggie and her claims (not supported with evidence) and the scientific literature.

Maggie also makes the interesting comment that anything which is safe to eat is generally safe to smear on one’s body before sex. Now lets explore this, now before some of you might think that this is going to be an exercise in school boy smut should understand that they will be disappointed if they expect Dr Foreman to be writing about something obscene.

We will start off with sugar containing products, now I know that many of us like sugar. It contributes to the taste of many nice and yummy products. It is found in fruit, sweets and many other products. I know that the food industry is accused of over using it, but when used in moderation it makes things taste very nice.

The problem I see is that sugar in the wrong place can result in mayhem, I would be interested to know if Maggie has considered the problem of Candida type yeasts. If one was to use some sugar rich substance as a lube, I see a danger that it might disturb the microbiology of the private parts. This could result in some rather unpleasant effects.

I also considered the possibility that Candida can feed on starch, I checked the academic literature and quickly I found an example of a form of Candida which can feed on starch. It so happens that the Candida tropicalis BPU1 isolated from goats can feed on potato, tapioca, or jack seed starch to form polyhydroxybutyrate (PHB). If you want to read the paper then see P. Priji, S. Sajith, S. Sreedevi, K.N. Unni, S. Kumar and S. Benjamin, Starch-Starke, 2016, 68(1-2), 57-66.

I looked in the literature for papers about starch and the yeast (Candida albicans) which is the form of candida common in humans, I found one by K. Bramono, R. Tsuboi and H. Ogawa (Mycoses, 1995, 38(9-10), 349-353) in which the authors reported that this yeast did not form alpha-amylase but it did form alpha-glucosidase. This is an enzyme which is able to break down starch into glucose. Also the yeast was able to grow on maltose which is a disaccharide. This suggests to me that it is possible that starch containing foods could cause something to happen, the final comment I will make on this organism is that by treatment with UV light and ethidium bromide it was possible to form a version of this yeast which was very good at converting starch into alcohol (ethanol). This was reported by A. Aruna, M. Nagavalli, V. Girijashankar, S.P.D. Ponamgi, V. Swathisree and L.V. Rao, Lettters in Applied Microbiology, 2015, 60(3), 229-236. While I hope it is unlikely that this mutant yeast would ever be able to escape from the lab or industry and establish itself in humans it does suggest that the parent version of the yeast can feed on starch.

In case you want to find out what ethidium bromide is then here is a picture of it, it is a nasty mutagenic dye used in DNA research.

Ethidium bromide

Ethidium bromide

I note that the KY liquid and the jelly both contain hydroxyethyl cellulose, in general cellulose is much harder to digest than a starch. This alone will make the KY gel much less likely to act as a food for the yeasts and bacteria. There are some organisms which have the enzymes needed to digest cellulose but many lifeforms are unable to do this. The paper by A. Martinez-Richa (Polymer, 1998, 39(14), 3115-3119) indicates that as the hydroxy groups in cellulose are replaced with 2-hydroxyethyl groups the rate of digestion by cytolase decreases. A series of products are sold under the names of cytolases, these are enzymes for the digestion of things like celluloses.

Now I can not claim to be an expert on the biology of Candida but this paper does raise a great concern. I think any of my readers who are concerned about starch based products being used for sexual purposes might be well advised to ask either a gynecologist or a microbiologist about this issue.

KY jelly as that sold in the UK contains some glycerol (propane-1,2,3-triol, Glycerin) which can be used by many microbes as a source of food but with the preservatives present in the gel I suspect that it will not be much of a problem. Glycerol can be used as a food by some bacteria, for example see A. Murarka, Y. Dharmadi, S.S. Yazdani and R. Gonzalez, Appl Environ Microbiol., 2008, 74(4), 1124–1135 explains how E. Coli can be used to convert glycerol into some industrial chemicals. It can also be used by some yeasts as a source of energy, but I suspect that the preservatives in the gel will stop this glycerol causing any problems.

Glycerol

Glycerol

The KY liquid also contains sorbitol and propylene glycol, these are polyalcohols which are non toxic. The sorbitol is a sugar which is slightly different to glucose, it provides less energy per gram and I suspect that it is a poorer fuel for bacteria / yeast than glucose would be. As it will only be present in a small amount I suspect that a small amount of this sugar will be less likely to cause some microbiological mayhem than a strong sugar solution such as honey.

D-Sorbitol (also known as D-Glucitol)

D-Sorbitol (also known as D-Glucitol)

The propylene glycol is a non toxic replacement for ethylene glycol which is used in both food and antifreezes. The reason it is far less toxic than ethylene glycol is that it can not be converted into oxalic acid or some other toxic C2 compound such as glycolaldehyde and glycolate (glycolic acid).

Propylene glycol

Propylene glycol

Likewise some gels such as KY jelly contain some gluconolactone which is a sugar, I do not know how much is present in the gel but due to the fact that the gel contains some antibacterials I suspect that this small trace of sugar will not pose a problem. This additive may be present to squester any unwanted trace metals which appear in the gel, this substance can chelate to a metal ion using the hydroxyl group which is alpha to the carboxylic acid which exists when it is in the open chain form. The addition of this to the product will be likely to increase the shelf life of it.

I have looked and the open chain version of this lactone has been converted into crystaline solids which have been investigated with X-ray crystallography, T. Lis, Acta Crystallogr.,Sect.B:Struct.Crystallogr.Cryst.Chem., 1979, 35, 1699 reports a polymeric manganese compound. Here two carboxylic acid groups (COOH) have lost a proton, these forms a negatively charged species which binds to the manganese cation (positive ion). At the same time an alcohol on the next carbon to the carboxylic acid binds to the manganese, two waters are attached to the manganese atom and to complete the metal complex an alcohol from the acid binds to the metal. I was going to draw a picture of it and then I saw the hydrogen bonding network, as I can not do justice to it I will not try to draw it.

The complex of this acid with a tris-(2-aminoethyl) amine complex of cobalt is more manageable, this is a simple complex which was documented by M.Pfister, S.Illi and P.Klufers, Z.Naturforsch.,B:Chem.Sci. , 2013, 68, 739 which explains clearly how I imagine that this molecule can bind to a metal. One of the advantages of binding to a metal is that it can make the metal less available for bacteria and other microbes to use. One of the ways in which a human body suppresses the growth of “germs” is by keeping its iron locked up in chemical forms which the germs can not access.

The KY jelly contains some chlorhexidine, this is an antibacterial agent which is used in mouth washes and many other antibacterial products. One interesting thing about chlorhexidine is that it can not be used at the same time as normal soap or an anionic detergent. This is due to the fact that the anionic detergents inactivate the chlorhexidine becuase the chlorhexidine is a cationic surfactant. The best detergents to use with chlorhexidine are neutral ones such as block copolymers of ethylene oxide and propylene oxide.

The gel also contains some sodium hydroxide, this might sound horrible but a small amount of sodium hydroxide when added to starch has an interesting effect. It causes the starch to swell up. This is because starch is a mild acid, starch is slightly more acidic than water so a slurry of starch will react with sodium hydroxide to form the sodium salt of the starch. I suspect that with the vast number of hydroxy groups present in hydroxyethyl cellulose that it can also bind to sodium ions in a similar way to corn starch.

So far I think that KY gel or another similar product designed and marketed by a mainstream drug company is going to provide you with a safe experience. Sadly no pharma company can offer a warranty that your sexual relationships will go perfectly and that you will live happily ever after with your partner. Well if only they could offer you such a deal !

I would also like to point something else out, those of my readers who are easily horrified should stop reading this post now ! Trust me this one is nasty with a capital N ! So not read the text in yellow if you are squeamish.

Many years ago as a PhD student I read of a nasty product tampering case in the USA. A man held an extreme belief that people who use contraception are going to bun in hell, regardless of how outlandish and offensive we might find this belief we can not criminalize a person’s belief or their thoughts. However acting on these beliefs or thoughts can be criminal. What this man did was to get a job in a condom factory, he decided to give the users of condoms an early taste of hell by smuggling an extra hot chili sauce into the factory which he later applied to the condoms while they are being packed.

He was convicted of a crime, and I think he was lucky to get away with probation. My father holds the view that this person should have got jail time as it was a hate crime. His reasoning is that a hate crime should earn the criminal a more lengthy stay inside. I have to agree with him on that. My legal adviser comments that a hate crime is a crime against society as a whole and not just the person or company which is being attacked.

Those of you of a sensitive nature can start reading again, this horrible story clearly shows that Maggie’s claim “When it comes to lube, if it is safe to eat, it is generally safe to apply” is clearly wrong. I think that the word “generally” is a funny word, it can have two meanings. It can either mean that the majority of things in a class are safe or it can mean all things in the class have the same characteristics, one can say that a chemical reaction is so general such that all substances of a given class will do reaction X. For example all secondary alcohols can react with chromium(VI) oxidants to form ketones. To my mind the use of “generally safe to apply is bad scientific writing as it can be understood in two very different ways. A good scientist or even a reasonable one will attempt to write and communicate in such a way that it is impossible to misunderstand the message.

While I might have picked an extreme example in the form of the capsaicins and the related compounds in chilli peppers, other foods contain substances which when taken in a particular way can cause injury. For example I know the inhalation of cinnamon powder his harmful (look up the cinnamon challenge and please for goodness sake do not try it).

I hold the view that many food substances might be safe to swallow in moderate amounts but when applied to the wrong part of the body the results can be rather disagreeable. Another example would be the fumes from onions and horseradish, while eating an onion or putting horseradish sauce on your beef might be OK. Exposing your eyes to the fumes from either is rather disagreeable.

It was interesting that Maggie Ney suggests oils as a alternative to these lubes made by the big companies, I have to question how good an idea this is. One sorry tale I know about is that relates to cosmetic breast implants. Now years ago as we all know silicone was marketed for breast implants. What happened was that a series of high profile court cases occurred when women claimed that their silicone implants harmed their health. Now I do not want to take sides over this matter. As a result of the court cases the world’s leading producer of silicone withdrew from the medical / cosmetic market so a search started anew for a new material for filling breast implants. One of the materials which was used was soy oil. Now we might think that something which is a food substance would be harmless for use in an implant and for smearing on our bodies. But there is a nasty sting in the tail in this case.

The subject has been reviewed by S. Monstrey, A. Christophe, J. Delanghe, S. De Vriese, M. Hamdi, K. Van Landuyt, and P. Blondeel, Plastic and Reconstructive Surgery, 2004, page 847. Here it is explained that the super refined soy oil used in the implants tends to react with oxygen to form new products including some which are carcinogenic. The idea of substances such as malondialdehyde sodium (3-hydroxy-2-propenal) forming inside my body is not a welcome or comforting idea. This compound is a dielectrophile which could crosslink biomolecules in a similar way to glyoxal. The malondialdehyde would be formed by the oxidation of the linoleic acid groups which are present in the soy oil. Other horrible oxidation products could form in the oil, I would like to know if Maggie knows about the problem of the instability of biodiesel, when compared with traditional road diesel fuel (DERV) made from petroleum the FAME biodiesel is more unstable. I have seen some papers in which oxidation processes which involve the carbon double bonds (unsaturation) are involved in some oxidation processes which are not possible in mixtures of alkanes or most alkyl aromatics (normal diesel fuel). I will assume that no one is going to try to create a diesel fuel which contains large amounts of cumene (isopropyl benzene) or similar compounds. Cumene is a rare example of a alkylarene which is very able to react with the oxygen of the air.

FAME biodiesel is a refined plant oil which has been converted into methyl esters. I would like to know how Maggie and the people who might follow her plan to keep the oils fresh without using things like BHT as a stabilizer. I know that many oils contain tocopherols but the more the oil is refined then the lower the greater the chance that these will be removed by the refining process. I would like to know if the natural tocopherol content of the oil will be sufficient to keep it from forming nasty chemicals by going rancid during storage. Again this is an example of how a food substance is not universally safe for humans.

Now while I have concentrated on American products, I would like to consider for a moment some Swedish products. Now some of my readers might misunderstand the Swedes and their attitude to sex, rather than either being rather repressed or sex mad what the Swedes are is “open” about sex. This does not mean that they do it in the open or public places, what this means is that they are willing to talk more openly about it than the British.

In Sweden there is an organisation named RFSU (Swedish Association for Sexuality Education) sell condoms, pregnancy tests and other sex related items. Now while some of their products are things which I would rather not discuss here they do sell lube. It is interesting that the Swedish version of the RFSU site has a link to the RFSU shop which is absent from the English version, I will have to tell RFSU about this. RFSU market a range of lubes, some of which are aqueous based products while they also market a silicone based lube. They also market a product which is both water and silicone based. I suspect that the product based on both silicone and water will be an emulsion. An emulsion is a combination of two liquids which are not miscible. I will not discuss the silicone based products any further in this post. We will save those for another day.

It is interesting that RFSU market some products which are free of parabens, for a list of what the Kick range contain see here. I considered the question of how does a paraben free product stay stable and I noticed that the aqueous product contains the following substances.

Aqua, Propylene Glycol, Glycerin, Hydroxyethylcellulose, Phenoxyethanol, Lactic Acid, Sodium Saccharin, Benzoic Acid, Sodium Hydroxide, Dehydroacetic Acid

This list might look long and scary, but lets go through it step by step.

Aqua is water, unless you are nervous of “dihydrogen monoxide” then I would not worry about this substance. We have already discussed propylene glycol and glyerin, they are similar to each other in their purpose and relatively harmless.

The hydroxyethyl cellulose is a version of cellulose which we have already considered. The phenoxyethanol is an interesting one. It is an antibacterial, while it is not paraben it is still a preservative.

phoch2ch2oh

Phenoxyethanol

The lactic acid and sodium hydroxide are likely to be there to control the pH. I know that in a normal woman that lactic acid is found in the vagina so the use of lactic acid plus some sodium hydroxide to set the pH of the product seems to be a very reasonable choice by the designers of the Swedish product.

lactic-acid

Lactic acid (2-hydroxypropanoic acid)

The sodium saccharin appears to be an odd choice of chemical, it is a sweetening agent used commonly in foods. But a quick search of the literature does reveal that it is able to inhibit bacteria. So it may be present to prevent microbes from spoiling the product. I also notice that benzoic acid is present, this is a substance which prevents the growth of yeasts, again a substance intended to make the product be more stable.

The last substance is dehydroacetic acid which has some antibacterial properties, it has been reported that Collie as a young man made some interesting discoveries about this substance. He found that it could be converted into orcinol. Sadly I know very little else about this substance other than the fact that it is a cyclic compound which is a masked polycarbonyl. The interesting thing is that both the Cambridge database and Wikipedia both have data which suggets that dehydroacetic acid is C8H8Owhile a book (Chemistry of Plant Natural Products: Stereochemistry, Conformation by Sunil Kumar Talapatra and Bani Talapatra) suggets that it is a slightly smaller molecule.

dehydroacetic-acid

Dehydroacetic acid and the ring opening reaction with water

But when we think about this moelcule it is clear that on heating under acidic conditions that it will lose carbon dioxide (decarboxylate) to form a triketone with the formula C7H8O3 which then undergoes an aldol reaction with itself followed by some minor reactions to form the orcinol. The triketone can form a cyclic compound with a formula of C7H8O2 which the book labeled as dehydroacetic acid.

The aldol reaction will form 3,5-dihydroxy-5-methylcyclohex-2-en-1-one which can dehydrate and then undergo a keto-enol tautomerism to become aromatic and thus form orcinol. Here is part of the reaction in the following figure.

steps towards orcinol.png

Formation of 3,5-dihydroxy-5-methylcyclohex-2-en-1-one from dehydroacetic acid.

What will happen next is that the dehydration and the keto-enol tautomerism will form the diphenol (orcinol).

orcinol-formation

Final stages of the formation of orcinol

While the formation of orcinol from dehydracetic acid is interesting, it is a bit of a diversion. I would like to point out that I know too little about dehydroacetic acid to be able to make a judgement as to how much is good or bad to put in a product. However looking at the Swedish product it does appear to be a product where none of the ingredients are screaming danger to me.

Lastly I would like to point out that soy oil will degrade condoms and also stain the sheets / clothing more than a water / hydroxyethyl cellulose based lube.

So far I am not convinced that “lube” is dangerous, unless you smear it on the vines which Tarzan swings from tree to tree with. I have taken the time to contact Maggie to see if she wishes to reply to some of the comments raised in this blog. But so far she has not chosen to comment.

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