Talk:Polysorbate 80

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Data, Other Names sections

It looks like someone lifted this detail from some dense, esoteric, industry report. Can someone make this section relevant and meaningful to the casual reader? I have no idea what the 'critical micelle concentration' is, or what concentrations of 0.012 mM and 0.006mM mean.

Also, the list of side effects should probably be paired down, and should probably be under a more appropriate section title than 'Other Names'. Thanks 128.148.184.11 (talk) 01:17, 17 March 2009 (UTC)[reply]

Surfactants can associate to form soluble spherical structures (micelles) in aqueous solution from 10's of nanometers up to microns in diameter (size depends upon the size of the molecule, and thermodynamics). This formation is concentration dependent, and the lowest concentration at which the micelles form is called the "critical micelle concentration". The unit mM stands for milli-molar, or rather 10^-3 moles/Liter.Biotechscientist (talk) 11:27, 4 November 2010 (UTC)[reply]

CMC

According to the Calbiochem Detergents Manual (found here: http://www.emdbiosciences.com/SharedImages/TechnicalLiterature/1_Detbooklet_2001.pdf), the CMC of Tween 80 is 0.012 mM. This differs by an order of magnitude from the value presented. Upon review of the Journal of Pharmaceutical Sciences article, it seems a typo was made in entering the value into this article. Ian Glenn 03:14, 29 April 2007 (UTC)[reply]

Fixed. -- Ed (Edgar181) 14:07, 23 April 2008 (UTC)[reply]

I have read this entire paper, there was not a typo. They measured it. Page 1376 in this article thoroughly explains why CMC's are functions of the solution properties (e.g. pH, ionic strength). The differences stem from the fact that Calbiochem measured the CMC in pure water whereas the CMC's measured in this article also contained Albutropin.Biotechscientist (talk) 12:14, 4 November 2010 (UTC)[reply]

External link

The link in the second reference (to Vlasic) is dead. --129.116.200.92 21:27, 15 November 2007 (UTC)[reply]

I have removed it. -- Ed (Edgar181)

Chemical structure

The structure shown in the figure is incorrect and does not match the given molecular formula. The oleic acid chain is missing a single -CH₂- group. --24.14.237.138 (talk) 01:50, 23 April 2008 (UTC)[reply]

I have corrected the error in the image. Thanks for catching it. -- Ed (Edgar181) 14:01, 23 April 2008 (UTC)[reply]

Not a Hydrocarbon

The opening paragraph ends with the sentence, "This synthetic compound is a viscous, water-soluble yellow liquid hydrocarbon." But, the definition of a hydrocarbon, given at the Wikipedia page, "Hydrocarbon", is, "an organic compound consisting entirely of hydrogen and carbon." All of the polysorbates include quite a few oxygen atoms. They can not accurately be called hydrocarbons. I will edit the page, removing, "hydrocarbon". 7802mark (talk) 15:40, 18 August 2016 (UTC)[reply]

Health effects

Studies have shown potentially serious health effects related to Tween 80. The anti HPV vaccine Gardasil contains Polysorbate 80, which is linked to infertility in mice,” noted Dee Nicholson, National Communications Director for Freedom in Canadian Health Care. [Nov 2007] Sleight of Handling: More Merck Magic Tricks With HPV Vaccine By Christopher C. Barr

A study published in December, 2005 discovered that Tween 80 can cause anaphylaxis, a sometimes fatal reaction characterized by a sharp drop in blood pressure, hives, and breathing difficulties. Researchers concluded that the severe reaction was not a typical allergic response characterized by the combination of IgE antibodies and the release of histamines; it was caused by a serious disruption that had occurred within the immune system.

In another study neonatal female rats were injected ip (0.1 ml/rat) with Tween 80 in 1, 5 or 10 percent aqueous solution on days 4-7 after birth. Treatment with Tween 80 accelerated maturation, prolonged the oestrus cycle, and induced persistent vaginal oestrus. The relative weight of the uterus and ovaries was decreased relative to the untreated controls. Squamous cell metaplasia of the epithelial lining of the uterus and cytological changes in the uterus were indicative of chronic oestrogenic stimulation. Ovaries were without corpora lutea, and had degenerative follicles.” ~ PMID: 8473002. Female lab rats injected with Tween 80 developed impaired sexual organs as well as premature development of their sexual organs. Institute of Preventive and Clinical Medicine, Limbová, Bratislava.

Previous studies by Gajdova et al. have shown that polysorbate 80 (also known as Tween 80) administered by intraperitoneal injection to neonatal female rats on days 4-7 after birth produced estrogenic effects including earlier vaginal opening, prolongation of the estrus cycle and persistent vaginal estrus. Some of these effects were evident many weeks after cessation of administration of polysorbate 80. [...] Thus, intrinsic estrogenic effects of polysorbate 80 reported following its intraperitoneal injection to neonatal 4-day-old female rats are not manifest when it is administered by oral gavage to immature 20- to 22-day-old female rats. This latter route of exposure is of more relevance to human exposure scenarios and these data are, therefore, important in assessing hazard/risk of polysorbate 80 to man. [Williams et al. - "The oral administration of Polysorbate 80 to the immature female rat does not increase uterine weight" https://www.sciencedirect.com/science/article/pii/S0378427496038635]

I deleted the list of possible side effects, I found the (probable) source of this information, and it's a list of side effects that can be caused by drugs in general, not Tween 80 specific at all. —Preceding unsigned comment added by 213.31.11.80 (talk) 09:21, 27 March 2009 (UTC)[reply]

Thank you for deleting this, Polysorbate 80 has a long history of usage in parenteral drug formulation, and is on the GRAS (generally recognized as safe) list of the FDA. The concentrations used in these formulations is very small, 0.05-0.1% (w/v).Biotechscientist (talk) 11:32, 4 November 2010 (UTC)[reply]

Also it should be noted, that injecting a 2kg rat with 0.1mL of a 10%(w/v) solution is a dosage 600 times higher (based on g/kg) than the common parenteral formulation of a 0.5 mL, 0.05%(w/v) solution into a child (30kg).Biotechscientist (talk) 11:50, 4 November 2010 (UTC)[reply]

Possible link to Crohn's Disease?

Is someone better qualified than I able to follow up on this? —Preceding unsigned comment added by 203.16.28.241 (talk) 09:14, 18 October 2010 (UTC) I am not aware of any link to Crohn's disease. Crohn's disease is an autoimmune disorder characterized more recently by the over production of a powerful cytokine TNF-alpha. I do not know the biodistribution of Polysorbate 80 alone, however I would consider it unlikely to upregulate the production of TNF-alpha. —Preceding unsigned comment added by Biotechscientist (talk • contribs) 11:17, 4 November 2010 (UTC)[reply]

references

15 & 18 are duplicates. 69.72.92.222 (talk) 07:14, 29 April 2015 (UTC)[reply]

Chemical structure of Polysorbate 80

The chemical structure shown for Polysorbate 80 appears to be incorrect. Polysorbate 80 is made by polymerization of 20 equivalents of ethylene oxide with sorbitan monooleate^[1]. The method of synthesis is summarized in Chapter 2 of Food Emulsifiers and Their Applications: Hasenhuettl, Gerard L., Hartel, Richard W. (Eds.)^[2]. Aside from the fact that sorbitan monooleate itself is not a pure substance, the polymerization with ethylene oxide can only modify the free hydroxyl groups. The oleic acid ester protects one of the hydroxyl groups from modification by reaction with ethylene oxide. Thus, there is not a synthetic basis for inclusion of a polyoxyethylene moiety adjacent to the oleate ester functionality in the structure provided. If one assumes that the major component of sorbitan monooleate arises from the esterification of the primary hydroxyl group of 1,4-sorbitan, then the only acceptable interpretation of the structure as shown would have w=0. Consequently, x+y+z=20 makes more sense.

Note that there is an unfortunate error in the structure of sorbitan monooleate in the book chapter cited, which shows a secondary ester. PubChem correctly depicts the primary ester of 1,4-sorbitan.

1. https://pubchem.ncbi.nlm.nih.gov/compound/9920342 2. Food Emulsifiers and Their Applications: Hasenhuettl, Gerard L., Hartel, Richard W. (Eds.), 2008 pg 25-6 , https://www.springer.com/us/book/9780387752839

JHCooke (talk) 21:56, 23 April 2018 (UTC)[reply]

References

^ 1
^ 2

Significance of "80" in the name of the compound

Where does the 80 come from? --Error (talk) 17:03, 14 October 2020 (UTC)[reply]

I'd love to see more visibility on this question. Would it help if I reply? I'm not trying to disrupt things in Wikipedia culture, but it's at the very bottom of the talk page and takes up like two centimeters of height on my display, almost two years after the question was posted. I'm curious about the 80 as well, and Googling the question brought me to the Wikipedia page, which doesn't answer the question. I wish there were a way to give this question more visibility within the community Tom Something (talk) 07:18, 1 September 2022 (UTC)[reply]

Related to the above, can anyone clarify the full chemical name of polysorbate 80? The Wikipedia page describes it as "Polyoxyethylene (80) sorbitan monooleate" but most chemical databases and papers that I can find describe it as "Polyoxyethylene (20) sorbitan monooleate" so what is more accurate?

Sources: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/170/000/p8466pis.pdf

https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:53426

https://academic.oup.com/jpp/article-abstract/25/6/470/6200958?redirectedFrom=fulltext&login=false Akkaz (talk) 12:43, 22 January 2023 (UTC)[reply]

Why does soap need a surfactant added to it?

I'm just curious about one of the uses listed. It says that it's added to soaps as a surfactant. But, soap by definition is a surfactant, so why would you need to add another surfactant to it? I suppose it's not exactly black and white where something either is or isn't a surfactant, it's probably more a gradient or spectrum.

So, conceivably they would add polysorbate-80 to give soap even more of a surfactant effect? But, I'm just speculating. I don't doubt that it's added to soaps, I've seen it myself in the ingredients. I'm just confused about the reason. Perhaps the article could expand a little on this for clarification. Even if just with a short sentence to give a bit more context. VoidHalo (talk) 15:59, 15 February 2024 (UTC)[reply]

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