Polysorbate 80

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Polysorbate 80[1]
Polysorbate 80.png
Names
IUPAC name
Polyoxyethylene (20) sorbitan monooleate
Other names
Alkest TW 80
Tween 80
Identifiers
9005-65-6 YesY
ChEMBL ChEMBL1697847 N
ChemSpider  YesY
RTECS number WG2932500
UNII 6OZP39ZG8H N
Properties
C64H124O26
Molar mass 1310 g/mol
Appearance Amber colored viscous liquid
Density 1.06–1.09 g/mL, oily liquid
Boiling point > 100°C
Very soluble
Solubility in other solvents soluble in ethanol, cottonseed oil, corn oil, ethyl acetate, methanol, toluene
Viscosity 300–500 centistokes (@25°C)
Hazards
Main hazards Irritant
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 113 °C (235 °F; 386 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Polysorbate 80 is a nonionic surfactant and emulsifier often used in foods and cosmetics. This synthetic compound is a viscous, water-soluble yellow liquid.

Chemistry[edit]

Polysorbate 80 is derived from polyethoxylated sorbitan and oleic acid. The hydrophilic groups in this compound are polyethers also known as polyoxyethylene groups, which are polymers of ethylene oxide. In the nomenclature of polysorbates, the numeric designation following polysorbate refers to the lipophilic group, in this case the oleic acid (see polysorbate for more detail).

The full chemical names for polysorbate 80 are:

  • Polyoxyethylene (20) sorbitan monooleate
  • (x)-sorbitan mono-9-octadecenoate poly(oxy-1,2-ethanediyl)

The critical micelle concentration of polysorbate 80 in pure water is reported as 0.012 mM.[2]

Other names[edit]

E number: E433

Brand names:

  • Alkest TW 80
  • Canarcel
  • Poegasorb 80
  • Tween 80 - Tween is a registered trademark of ICI Americas, Inc.[3]

Uses[edit]

Food use[edit]

Polysorbate 80 is used as an emulsifier in foods.

For example in ice cream, polysorbate is added up to 0.5% (v/v) concentration to make the ice cream smoother and easier to handle, as well as increasing its resistance to melting.[4] Adding this substance prevents milk proteins from completely coating the fat droplets. This allows them to join together in chains and nets, which hold air in the mixture, and provide a firmer texture that holds its shape as the ice cream melts.

Health and beauty use[edit]

Polysorbate 80 is also used as a surfactant in soaps and cosmetics, or a solubilizer such as in a mouthwash. The cosmetic grade of polysorbate 80 may have more impurities than the food grade.[5]

Medical use[edit]

Polysorbate 80 is an excipient that is used to stabilize aqueous formulations of medications for parenteral administration, and used as an emulsifier in the manufacture of the popular antiarrhythmic amiodarone.[6] It is also used as an excipient in some European and Canadian influenza vaccines.[7] It is also used in the culture of Mycobacterium tuberculosis in Middlebrook 7H9 broth. It is also used as an emulsifier in the estrogen-regulating drug Estrasorb.[8] Influenza vaccines contain 25 μg of polysorbate 80 per dose.[9]

Laboratory use[edit]

Some mycobacteria contain a type of lipase (enzyme that breaks up lipid molecules). When added to a mixture of polysorbate 80 and phenol red, they cause the solution to change colour, so this is used as a test to identify the phenotype of a strain or isolate.

Consumption and potential effects[edit]

Safe and well tolerated[edit]

In Europe and America, people eat about 100 mg of polysorbate 80 in foods per day on average.[10] In general, polysorbate 80 is safe and well tolerated. Polysorbate 80 is not carcinogenic. Rats fed with diets containing up to 5% polysorbate 80 by volume for 12 weeks showed no toxic effects.[11] A 1997 study on two rats looked at the effect of consuming three doses by body weight of 0.5%/day on the sex organs of female rats and saw no abnormal changes in uterine weight.[12]

Crohn's disease[edit]

A small number of people may be sensitive to polysorbate 80,[13] and it may be harmful to people with Crohn's disease.[14][15]

Lowered body weight of offspring[edit]

A 2008 animal study concluded no observable adverse effects were seen at doses per body weight up to 1.85 ml/kg·day, which is equivalent to a 70 kg person consuming about 140 g of this substance per day for 21 days. However, administration of 16.783 ml/kg·day to pregnant rats lowered body weight in male and female offspring.[10] This is equivalent to a person consuming about 1.3 kg of polysorbate 80 per day for 21 days.

Decreased fertility[edit]

A 1956 study saw no effect on reproduction in rats at up to 5% of their diet being polysorbate 80, although reproduction decreased at 20% of the diet (duration of study?).[16] A 1993 study raised concerns that polysorbate 80 might decrease fertility in rats.[17]

Impact on mouse gut microbiota[edit]

Relatively low concentrations of two commonly used emulsifiers, namely carboxymethylcellulose and polysorbate-80, induced low-grade inflammation and obesity/metabolic syndrome in wild-type hosts and promoted robust colitis in mice predisposed to this disorder. Use of germ-free mice and fecal transplants indicated that such changes in microbiota were necessary and sufficient for both low-grade inflammation and metabolic syndrome. [18]

See also[edit]

References[edit]

  1. ^ Merck Index, 13th Edition, 7664.
  2. ^ Chou DK, Krishnamurthy R, Randolph TW, Carpenter JF, Manning MC (June 2005). "Effects of Tween 20 and Tween 80 on the stability of Albutropin during agitation". J Pharm Sci 94 (6): 1368–81. doi:10.1002/jps.20365. PMID 15858848. 
  3. ^ US PTO TESS Registry Number 2885675
  4. ^ Goff, H. Douglas (1997). "Colloidal aspects of ice cream—A review". International Dairy Journal 7 (6–7): 363–373. doi:10.1016/S0958-6946(97)00040-X. ISSN 0958-6946. 
  5. ^ "What is Polysorbate 80?". The Honest Company Blog. The Honest Company. Retrieved 24 April 2014. 
  6. ^ Gautier & Bellamy. "Pharmaceutical amiodarone composition for parenteral delivery". Retrieved 2008-04-06. 
  7. ^ Pandemic H1N1 (pH1N1) Influenza Vaccine Quick Reference Guide Winnipeg Regional Health Authority 2009
  8. ^ http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21371_estrasorb_lbl.pdf
  9. ^ Cite error: The named reference H1N12 was invoked but never defined (see the help page).
  10. ^ a b Ema, M.; Hara, H.; Matsumoto, M.; Hirata-Koizumi, M.; Hirose, A.; Kamata, E. (2008). "Evaluation of developmental neurotoxicity of polysorbate 80 in rats". Reproductive Toxicology 25 (1): 89–52. doi:10.1016/j.reprotox.2007.08.003. PMID 17961976.  edit
  11. ^ OSER BL, OSER M (November 1956). "Nutritional studies on rats on diets containing high levels of partial ester emulsifiers. I. General plan and procedures; growth and food utilization". J. Nutr. 60 (3): 367–90. PMID 13377228. 
  12. ^ Williams J, Odum J, Lewis RW, Brady AM (March 1997). "The oral administration of polysorbate 80 to the immature female rat does not increase uterine weight". Toxicol. Lett. 91 (1): 19–24. doi:10.1016/S0378-4274(96)03863-5. PMID 9096282. 
  13. ^ Steele RH, Limaye S, Cleland B, Chow J, Suranyi MG (2005). "Hypersensitivity reactions to the polysorbate contained in recombinant erythropoietin and darbepoietin". Nephrology (Carlton) 10 (3): 317–20. doi:10.1111/j.1440-1797.2005.00389.x. PMID 15958049. 
  14. ^ Roberts, Carol L; Keita, A. V.; Duncan, S. H.; O'Kennedy, N.; Soderholm, J. D.; Rhodes, J. M.; Campbell, B. J. (2010-09-01). "Translocation of Crohn's disease Escherichia coli across M-cells: contrasting effects of soluble plant fibres and emulsifiers". Gut 59 (10): 1331–1339. doi:10.1136/gut.2009.195370. PMC 2976079. PMID 20813719. Retrieved 2010-12-20. Lay summary (2010-08-30). 
  15. ^ "Dietary emulsifiers impact the mouse gut microbiota promoting colitis and metabolic syndrome", Nature 519, 92–96 (05 March 2015) doi:10.1038/nature14232 Received 05 December 2013 Accepted 14 January 2015 Published online 25 February 2015 | http://www.nature.com/nature/journal/v519/n7541/full/nature14232.html
  16. ^ OSER BL, OSER M (December 1956). "Nutritional studies on rats of diets containing high levels of partial ester emulsifiers. II. Reproduction and lactation". J. Nutr. 60 (4): 489–505. PMID 13385715. 
  17. ^ Gajdová M, Jakubovsky J, Války J (March 1993). "Delayed effects of neonatal exposure to Tween 80 on female reproductive organs in rats". Food Chem. Toxicol. 31 (3): 183–90. doi:10.1016/0278-6915(93)90092-D. PMID 8473002. 
  18. ^ Chassaing, B et al. (March 5, 2015). "Dietary emulsifiers impact the mouse gut microbiota promoting colitis and metabolic syndrome.". Nature 519 (7541): 92–6. doi:10.1038/nature14232. PMID 25731162.