Chemistry:Listerine

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Short description: Brand of mouthwash
Listerine
Listerine logo.svg
Listerine products.jpg
Various Listerine products in Canada
Product typeMouthwash, toothpaste, fluoride rinse, quick-dissolving strips, chewable tablets, breath spray, dental floss
OwnerMcNeil Consumer Healthcare division of Kenvue
CountryUnited States
Introduced1879 (original formula)
1914 (over the counter)
Related brandsPlax
Previous owners
  • Lambert Pharmacal Company
  • Warner–Lambert
  • Pfizer
  • Johnson & Johnson
Tagline"Kills germs that cause bad breath"
"Bring Out the Bold"
Websitewww.listerine.com

Listerine is an American brand of antiseptic mouthwash that is promoted with the slogan "Kills germs that cause bad breath". Named after Joseph Lister, who pioneered antiseptic surgery at the Glasgow Royal Infirmary in Scotland, Listerine was developed in 1879 by Joseph Lawrence, a chemist in St. Louis, Missouri.[1][2]

Originally marketed by the Lambert Pharmacal Company (which later became Warner–Lambert), Listerine has been manufactured and distributed by Johnson & Johnson since that company's acquisition of Pfizer's consumer healthcare division on December 20, 2006.[3]

The Listerine brand name is also used in toothpaste, chewable tablets, and self-dissolving teeth-whitening strips.

History

1925 advertisement

Inspired by Louis Pasteur's ideas on microbial infection, the English doctor Joseph Lister demonstrated in 1865 that use of carbolic acid on surgical dressings would significantly reduce rates of post-surgical infection. Lister's work in turn inspired St. Louis-based doctor Joseph Lawrence to develop an alcohol-based formula for a surgical antiseptic which included eucalyptol, menthol, methyl salicylate, and thymol (its exact composition was a trade secret). Lawrence named his antiseptic "Listerine" in honor of Lister.[4]

Lawrence hoped to promote Listerine's use as a general germicide as well as a surgical antiseptic, and licensed his formula to a local pharmacist named Jordan Wheat Lambert in 1881. Lambert subsequently started the Lambert Pharmacal Company, marketing Listerine.[4] Listerine was promoted to dentists for oral care in 1895[5] and was the first over-the-counter mouthwash sold in the United States, in 1914.[6]

Lambert's licensing agreement with Lawrence required that he and his "heirs, executors and assigns" be paid royalties by Lambert or its successors for each bottle sold in perpetuity, until such time that Lambert or its successors ceases manufacturing Listerine.[7] Most of these royalty shares are held by Lawrence's heirs. Real estate broker John Reynolds bought a roughly 50% stake in the royalties in the 1950's, which he then transferred to the Archdiocese of New York, and was later resold to other parties to help fund the diocese. The Salvation Army, American Bible Society, and Wellesley College also held shares in Listerine royalties.[8][7]

Listerine entered common household use after Jordan Wheat Lambert's son Gerard Lambert joined the company and promoted an aggressive marketing campaign.[4] According to Steven D. Levitt and Stephen J. Dubner's book Freakonomics:[9]

Listerine, for instance, was invented in the nineteenth century as powerful surgical antiseptic. It was later sold, in distilled form, as both a floor cleaner and a cure for gonorrhea. But it wasn't a runaway success until the 1920s, when it was pitched as a solution for "chronic halitosis" — a then obscure medical term for bad breath. Listerine's new ads featured forlorn young women and men, eager for marriage but turned off by their mate's rotten breath. "Can I be happy with him in spite of that?" one maiden asked herself. Until that time, bad breath was not conventionally considered such a catastrophe. But Listerine changed that. As the advertising scholar James B. Twitchell writes, "Listerine did not make mouthwash as much as it made halitosis." In just seven years, the company's revenues rose from $115,000 to more than $8 million.

In 1955, Lambert Pharmacal merged with New York-based Warner-Hudnut and became Warner-Lambert Pharmaceutical Company, and incorporated in Delaware with its corporate headquarters in Morris Plains, New Jersey.[10] Following the merger, Warner-Lambert attempted to back out of the aforementioned royalty agreements with Lawrence by filing a lawsuit in the United States District Court for the Southern District of New York. The company cited that the payments were based upon Listerine's formula having initially been a trade secret, but that since the formula had been published in 1931, the property no longer had a value, and that the indefinite agreement was legally unreasonable. The court, however, ruled in favor of Lawrence and the defendants, citing that the conditions were plainly-worded, implicit, and could be waived by ending production of the product.[7][11][12]

In 2000, Pfizer acquired Warner-Lambert.[13] Among Lambert's assets was the original land for Lambert-St. Louis International Airport.[14]

Glass bottle with paper label. The screw top indicates that the bottle was manufactured post-1920s.

From 1921 until the mid-1970s, Listerine was also marketed as preventive and remedy for colds and sore throats. In 1976, the Federal Trade Commission ruled that these claims were misleading, and that Listerine had "no efficacy" at either preventing or alleviating the symptoms of sore throats and colds. Warner-Lambert was ordered to stop making the claims, and to include in the next $10.2 million worth of Listerine ads specific mention that "Listerine will not help prevent colds or sore throats or lessen their severity."[15] The advertisement run by Listerine added the preamble "contrary to prior advertising".[16]

For a short time, beginning in 1927, the Lambert Pharmaceutical Company marketed Listerine Cigarettes.[17][18]

From the 1930s into the 1950s, advertisements claimed that applying Listerine to the scalp could prevent "infectious dandruff".[19]

Listerine was packaged in a glass bottle inside a corrugated cardboard tube for nearly 80 years before the first revamps were made to the brand: in 1992, Cool Mint Listerine was introduced in addition to the original Listerine Antiseptic formula and, in 1994, both brands were introduced in plastic bottles for the first time. In 1995, FreshBurst was added,[20] then in 2003 Natural Citrus.[citation needed] In 2006 a new addition to the "less intense" variety, Vanilla Mint, was released. Nine different kinds of Listerine are on the market in the U.S. and elsewhere: Original, Cool Mint, FreshBurst, Natural Citrus, Naturals, Soft Mint (Vanilla Mint), UltraClean (formerly Advanced Listerine), Tooth Defense (mint shield), and Whitening pre-brush rinse (clean mint).[citation needed] In the United Kingdom, where in recent years the only option for most residents to obtain the original Listerine was to purchase from a dwindling number of larger branches of Boots the Chemist only the flavoured products are now obtainable as Boots has removed the Original from its selection.[21] Original is not listed on the Listerine UK website as among the Listerine products available in the United Kingdom.[22]

Composition

According to the product overview, the ingredients are as following for Listerine Total Care.[23] Similar distribution is contained in other varieties, which also list the essential oils as active ingredients.[24]

Listerine Total Care

Active ingredient

Inactive ingredients

  • Water
  • Sorbitol
  • Alcohol (21.6% v/v)
  • Poloxamer 407
  • Sodium Saccharin
  • Flavor
  • Eucalyptol
  • Methyl Salicylate
  • Thymol
  • Phosphoric Acid
  • Menthol
  • Disodium Phosphate
  • Sucralose
  • Red 40
  • Blue 1

Distributions in case of Listerine Antiseptic Mouthwash, Original-05/22/2008 for essential oils are: menthol (mint) 0.042%, thymol (thyme) 0.064%, methyl salicylate (wintergreen) 0.06%, and eucalyptol (eucalyptus) 0.092%.[25]

Benefits

In combination all have an antiseptic effect[26] and there is some thought that methyl salicylate may have an anti inflammatory effect as well.[27] Ethanol, which is toxic to bacteria at concentrations of 40%,[28] is present in concentrations of 21.6%[23] in the flavored product and 26.9%[29] in the original gold Listerine Antiseptic.[30] At this concentration, the ethanol serves to dissolve the active ingredients.[31][32]

Research indicates that Listerine can reduce dental plaque by 22.2% and gingivitis by 28.2% at 6 months. Dental plaque by 20.8% and gingivitis by 27.7% at 6 months, when compared with vehicle in test. Vehicle was 26.9% hydroalcoholic containing all ingredients in Listerine Antiseptic except its essential oils.[33][34]

Listerine also sell a formulation called Listerine Advanced Defence Gum Treatment containing a common food preservative, ethyl lauroyl arginate (LAE) at 0.147%.[35]

Safety

Alcohol misuse

The addition of essential oils means the ethanol is considered to be undrinkable, known as denatured alcohol, and it is therefore not regulated as an alcoholic beverage in the United States. (Specially Denatured Alcohol Formula 38-B, specified in Title 27, Code of Federal Regulations, Part 21, Subpart D) However, consumption of mouthwash to obtain intoxication does occur, especially among alcoholics and underage drinkers.[36]

Cancer risk

There has been concern that the use of alcohol-containing mouthwash such as Listerine may increase the risk of developing oral cancer.[37][38] As of 2010, seven meta-analyses have found no connection between alcohol-containing mouthwashes and oral cancer, and three have found increased risk.[39] In January 2009, Andrew Penman, chief executive of The Cancer Council New South Wales, called for further research on the matter.[38] In a March 2009 brief, the American Dental Association said "the available evidence does not support a connection between oral cancer and alcohol-containing mouthrinse".[40]

In 2009, Johnson and Johnson launched a new alcohol-free version of the product called Listerine Zero.[29]

A 2020 systematic review investigated the controversial alcohol-oral cancer question (or oropharynx or other head and neck cancers), saying that for example "this risk from alcohol consumption increases ten times in heavy drinkers compared to abstainers or irregular drinkers" but there is no consensus whether it is a risk factor. The authors of the study conclude that "alcohol-based mouthwash consumption significantly increases salivary acetaldehyde levels in the first few minutes. However, no evidence exists if long-term salivary acetaldehyde levels may increase with a high frequency of mouthwash use. There is still insufficient evidence of whether the use of alcohol-based mouthwash is an independent risk factor for oral or oropharynx cancer. Nonetheless, it does increase the risk when it occurs concomitantly with other risk factors such as smoking or alcohol.[41]

Contaminants

On April 11, 2007, McNeil-PPC disclosed that there were potentially contaminants in all Listerine Agent Cool Blue products sold since its launch in 2006, and that all bottles were being recalled.[42] The recall affected some 4,000,000 bottles sold since that time.[43] According to the company, Listerine Agent Cool Blue is the only product affected by the contamination and no other products in the Listerine family were under recall.[42]

References

  1. ↑ Newton, David (2008). Trademarked : a history of well-known brands, from Aertex to Wright's Coal Tar. Stroud: Sutton Publishing. ISBN 978-0750945905. https://books.google.com/books?id=HekTDQAAQBAJ&pg=PT447. 
  2. ↑ "History of LISTERINE®" (in en). https://www.listerine.com/about. 
  3. ↑ "Johnson & Johnson Acquires Pfizer Consumer Healthcare". Lexpert. December 20, 2006. https://www.lexpert.ca/article/johnson-and-johnson-acquires-pfizer-consumer-healthcare/?p=%7C273&sitecode=DIR. 
  4. ↑ 4.0 4.1 4.2 Hicks, Jesse. "A Fresh Breath". Chemical Heritage Foundation. http://www.chemheritage.org/discover/online-resources/thanks-to-chemistry/listerine.aspx. 
  5. ↑ "Prescribe Listerine for Patients". The Pacific Dental Journal 5 (2): 58. 1895. https://books.google.com/books?id=bU0dAQAAMAAJ&pg=PA58. Retrieved 27 January 2015. 
  6. ↑ Casey, Wilson (2009). Firsts: Origins of Everyday Things That Changed the World. New York: Penguin. p. 155. ISBN 978-1101159460. https://books.google.com/books?id=OXT0MyOjhnIC&pg=PT155. Retrieved 27 January 2015. 
  7. ↑ 7.0 7.1 7.2 Susan, Decker (2020-07-13). "Bad Breath Offers a Rare Payoff in Listerine-Royalty Stake Sale". https://www.bloomberg.com/news/articles/2020-07-13/bad-breath-offers-a-rare-payoff-in-listerine-royalty-stake-sale. 
  8. ↑ "Corporations: Riches from Royalties" (in en-US). Time. 1966-12-16. ISSN 0040-781X. https://content.time.com/time/subscriber/article/0,33009,836695,00.html. Retrieved 2022-07-27. 
  9. ↑ Levitt, Steven D.; Dubner, Stephen J. (2009). Freakonomics : A Rogue Economist Explores The Hidden Side Of Everything. New York City: HarperCollins. p. 87. ISBN 978-0-06-073133-5. OCLC 502013083. http://freakonomicsbook.com/. 
    Previous editions of Freakonomics incorrectly described halitosis as a "faux medical term", which this Wikipedia article previously reflected.
  10. ↑ "Warner-Hudnut, Inc. ( Early Warner-Lambert Company )". http://www.goantiques.com/detail,warner-hudnut-early,345642.html. 
  11. ↑ "When the Secret Enables the Brand: The Long-Lasting Listerine License" (in en). 2021-11-23. https://www.ipwatchdog.com/2021/11/23/secret-enables-brand-long-lasting-listerine-license/id=140353/. 
  12. ↑ "Warner-Lambert Pharm. Co. v. John J. Reynolds, Inc., 178 F. Supp. 655 (S.D.N.Y. 1959)" (in en). https://law.justia.com/cases/federal/district-courts/FSupp/178/655/1642490/. 
  13. ↑ "2000: Pfizer joins forces with Warner-Lambert". http://www.pfizer.com/about/history/pfizer_warner_lambert.jsp. 
  14. ↑ Mary Delach Leonard (Dec 25, 2016). "Lambert airport traces its history to an aviation visionary who knew how to sell mouthwash". http://news.stlpublicradio.org/post/lambert-airport-traces-its-history-aviation-visionary-who-knew-how-sell-mouthwash#stream/0. 
  15. ↑ "Three by the FTC". Time (magazine). Jan 5, 1976. http://content.time.com/time/magazine/article/0,9171,947635,00.html. Retrieved 2006-12-05. 
  16. ↑ Business Its Legal, Ethical, and Global Environment by Marianne M. Jennings 8th edition page 324, Given these safeguards, we believe the preamble "Contrary to prior advertising" is not necessary.
  17. ↑ Gardiner, Phillip (2004). "The African Americanization of menthol cigarette use in the United States". Nicotine & Tobacco Research 6: S55–65. doi:10.1080/14622200310001649478. PMID 14982709. http://www.determinedtoquit.net/howtoquit/methodsofquitting/faithbasedmethods/ltnmaterials/AfricanAmericanizationMenthol.pdf. Retrieved 2014-08-15. 
  18. ↑ "LISTERINE Cigarettes". http://tobaccodocuments.org/pollay_ads/List01.01.html. 
  19. ↑ Lambert Pharmacal (1930). "Listerine gets rid of dandruff". Popular Science 116 (5): 17. ISSN 0161-7370. https://books.google.com/books?id=OigDAAAAMBAJ&pg=PA17. 
  20. ↑ "Article: Warner-Lambert reenters the dentrifice business.". Chain Drug Review. 1995-07-31. http://www.highbeam.com/doc/1G1-17282221.html. Retrieved 2014-08-16. 
  21. ↑ "Boots website: Listerine products selection". https://www.boots.com/sitesearch?searchTerm=listerine. 
  22. ↑ "Products" (in en). https://www.listerine.co.uk/products. 
  23. ↑ 23.0 23.1 "TOTAL CARE Anticavity Fluoride Mouthwash" (in en). https://www.listerine.com/mouthwash/listerine-total-care/listerine-total-care-anticavity-mouthwash. 
  24. ↑ "LISTERINE® Gum Therapy Antiseptic Mouthwash" (in en). https://www.listerine.com/mouthwash/antisepctic/listerine-gum-therapy-antiseptic-mouthwash. 
  25. ↑ "Listerine Antiseptic Mouthwash, Original-05/22/2008". http://whatsinproducts.com/types/type_detail/1/9569/standard/Listerine%20Antiseptic%20Mouthwash,%20Original-05/22/2008/10-001-115. 
  26. ↑ Bachir, Raho G; Benali, M (September 2012). "Antibacterial activity of the essential oils from the leaves of Eucalyptus globulus against Escherichia coli and Staphylococcus aureus". Asian Pacific Journal of Tropical Biomedicine 2 (9): 739–742. doi:10.1016/S2221-1691(12)60220-2. ISSN 2221-1691. PMID 23570005. 
  27. ↑ Mason, L.; Moore, R. A.; Edwards, J. E.; McQuay, H. J.; Derry, S.; Wiffen, P. J. (2004). "Systematic review of efficacy of topical rubefacients containing salicylates for the treatment of acute and chronic pain". BMJ (Clinical Research Ed.) 328 (7446): 995. doi:10.1136/bmj.38040.607141.EE. PMID 15033879. 
  28. ↑ Reynolds, Scott A.; Levy, Foster; Walker, Elaine S. (March 2006). "Hand Sanitizer Alert". Emerging Infectious Diseases 12 (3): 527–529. doi:10.3201/eid1203.050955. ISSN 1080-6040. PMID 16710985. 
  29. ↑ 29.0 29.1 "Johnson & Johnson sued over mouthwash cancer fears" (in en). 2011-08-27. http://www.theguardian.com/world/2011/aug/27/johnson-johnson-sued-mouthwash-cancer-fears. 
  30. ↑ Block's disinfection, sterilization, and preservation. Gerald E. McDonnell, Joyce M. Hansen (6th ed.). Philadelphia. 2021. ISBN 978-1-4963-8149-1. OCLC 1149169039. https://www.worldcat.org/oclc/1149169039. 
  31. ↑ "Alcohol" (in en-gb). https://www.listerineprofessional.co.uk/safety-profile/listerine-alcohol. 
  32. ↑ "Alcohol in Mouthwashes & Rinses | LISTERINE® Professional" (in en). https://www.listerineprofessional.com/the-science-of-listerine/evidence-of-safety/role-of-alcohol. 
  33. ↑ "Removing Plaque from Teeth | LISTERINE® Professional" (in en). https://www.listerineprofessional.com/the-science-of-listerine/evidence-of-efficacy/product-data/removing-plaque-from-teeth-study. 
  34. ↑ Gordon, J. M.; Lamster, I. B.; Seiger, M. C. (September 1985). "Efficacy of Listerine antiseptic in inhibiting the development of plaque and gingivitis". Journal of Clinical Periodontology 12 (8): 697–704. doi:10.1111/j.1600-051x.1985.tb00941.x. ISSN 0303-6979. PMID 3902908. https://pubmed.ncbi.nlm.nih.gov/3902908/. 
  35. ↑ "Product profile". https://www.listerine.ie/products/healthy-gums/listerine-advanced-defenced-gum-treatment. 
  36. ↑ Cathleen Terhune Alty (March 12, 2014). "Do you want that mouthwash straight up or on the rocks?". http://www.rdhmag.com/articles/print/volume-34/issue-3/features/do-you-want-that-mouthwash-straight-up-or-on-the-rocks.html. 
  37. ↑ McCullough, Michael; Farah, C.S. (December 2008). "The role of alcohol in oral carcinogenesis with particular reference to alcohol-containing mouthwashes". Australian Dental Journal 53 (4): 302–305. doi:10.1111/j.1834-7819.2008.00070.x. PMID 19133944. 
  38. ↑ 38.0 38.1 Weaver, Clair (January 10, 2009). "Mouthwash linked to cancer". The Daily Telegraph. http://www.dailytelegraph.com.au/news/sydney-news/mouthwash-linked-to-cancer/story-e6freuzi-1111118530255. 
  39. ↑ La Vecchia, C (2009). "Mouthwash and oral cancer risk: An update". Oral Oncology 45 (3): 198–200. doi:10.1016/j.oraloncology.2008.08.012. PMID 18952488. 
  40. ↑ Science brief on alcohol-containing mouthrinses and oral cancer, American Dental Association, March 2009
  41. ↑ Ustrell-Borràs, M; Traboulsi-Garet, B; Gay-Escoda, C (2020). "Alcohol-based mouthwash as a risk factor of oral cancer: A systematic review". Medicina Oral Patología Oral y Cirugia Bucal 25 (1): e1–e12. doi:10.4317/medoral.23085. PMID 31655832. PMC 6982979. http://www.medicinaoral.com/medoralfree01/aop/23085.pdf. 
  42. ↑ 42.0 42.1 "McNeil-PPC, Inc. today issues voluntary nationwide consumer recall of Listerine Agent Cool Blue plaque-detecting rinse products" (Press release). McNeil-PPC. 2007-04-11. Retrieved 2014-04-10.
  43. ↑ "Contamination prompts J&J recall of Listerine Agent Cool Blue plaque-detecting rinse". NBC News. Associated Press. 2007-04-12. http://www.nbcnews.com/id/18073946/ns/health-childrens_health/t/listerine-recalls-childrens-plaque-rinse/. 

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