Polysorbate 80

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Structural formula
"Typical" structure of polysorbate 80
Typical structure of polysorbate 80
(w + x + y + z = 20)
"Mixture of partial esters of fatty acids, mainly oleic acid , with sorbitol and its anhydrides, which are ethoxylated with about 20 moles of ethylene oxide for every mole of sorbitol and sorbitol anhydride."
General
Surname Polysorbate 80
other names
  • Polyoxyethylene (20) sorbitan monooleate ( IUPAC )
  • Tween ® 80 ( trade name )
  • E  433
Molecular formula C 64 H 124 O 26
Brief description

clear to slightly opalescent yellowish to brownish-yellowish, oily, odorless liquid

External identifiers / databases
CAS number 9005-65-6
EC number 500-019-9
ECHA InfoCard 100.105.529
PubChem 5281955
ChemSpider 4447515
DrugBank DB11063
Wikidata Q420358
properties
Molar mass 1309.66 g · mol -1
Physical state

liquid

density

1.064 g cm −3 (20 ° C)

boiling point

> 100 ° C

Vapor pressure

<1 hPa (20 ° C)

solubility

soluble in water, ethanol (anhydrous), methanol and ethyl acetate

Refractive index

1.4750 (20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

38,000 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Polysorbate 80 is a surface-active substance that is used as an emulsifier and wetting agent in foods, cosmetics and pharmaceuticals, for example.

properties

Polysorbate 80 is a polyoxyethylated compound derived from sorbitol and oleic acid. The hydrophilic groups of this nonionic surfactant are polyethers, polymers of a total of 20 ethylene oxides . The viscosity is 425 mPa · s, Polysorbate 80 has an HLB value of 15.0 and is therefore suitable for the production of oil-in-water (O / W) emulsions.

The pH value of a 5% aqueous solution is 5–7, the flash point is> 149 ° C. The critical micelle concentration (CMC) is 1.2 · 10 −5 mol / l in water at 25 ° C.

use

Polysorbate 80 is mainly used in dishes, especially in pickled foods, as an emulsifier and stabilizer. It is often used in ice cream to prevent the milk proteins from completely enclosing the fat droplets. Instead, they form chains and web structures that hold air in the mix. This creates a firmer structure that helps the ice cream retain its shape as it melts.

It is approved in the EU as a food additive with the number E  433 . It is largely chemically and biologically inert .

Polysorbate 80 is used in the pharmaceutical industry for virus inactivation of blood products and is used as a solubilizer and emulsifier in the manufacture of drugs to emulsify oily ( lipophilic ) substances in aqueous bases. It is one of the few surface-active substances that is parenterally compatible.

Particularly pure qualities are required for drug manufacture, in pharmacopoeia specified.

Manufacturing

The esterification of sorbitol and its anhydrides ( sorbitan ) with oleic acid produces sorbitan fatty acid esters . This reacts with ethylene oxide in a polyaddition , as a result of which polyoxyethylene chains are formed, to form the polysorbate .

safety instructions

In 2015, a study was published in the journal Nature that proves that a 1 percent proportion of polysorbate 80 in the drinking water of mice causes disturbances in the intestinal flora, intestinal inflammation and weight gain over a period of 12 weeks. On the intestinal wall, a 2/3 reduction in the protective mucus layer was found. Draize test on rabbits , via the eye: 150 mg, slightly irritating.

Environmental information

Polysorbate 80 has an LC 50 value of> 471 mg / l in 96 h in rainbow trout ( Onchorhynchus mykiss ).

Related substances

Other representatives from the group of polysorbates are:

Individual evidence

  1. ↑ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 3722–3723, ISBN 978-3-7692-3962-1 .
  2. ↑ a b Entry for E 433: Polyoxyethylene sorbitan monooleate (polysorbate 80) in the European database for food additives, accessed on June 27, 2020.
  3. ↑ a b c F. von Bruchhausen (Ed.), G. Dannhardt, S. Ebel et al .: Hager's Handbook of Pharmaceutical Practice. Volume 9: fabrics PZ, 5th edition, Springer, Berlin 1993, p. 289 ff.
  4. ↑ a b c d e f Datasheet Polysorbate 80 at AlfaAesar, accessed on December 26, 2019 ( PDF )(JavaScript required) .
  5. ↑ Entry on Polysorbate 80 in the ChemIDplus database of the United States National Library of Medicine (NLM)
  6. ↑ a b c Datasheet Polysorbate 80 (PDF) from Carl Roth , accessed on December 14, 2010.
  7. ↑ Chou, DK et al. (2005): Effects of Tween 20 and Tween 80 on the stability of Albutropin during agitation. In: J. Pharm. Sci. Vol. 94, pp. 1368-1381; PMID 15858848 ; doi : 10.1002 / jps.20365
  8. ↑ B. Chassaing, O. Koren, JK Goodrich, AC Poole, S. Srinivasan, RE Ley, AT Gewirtz: Dietary emulsifiers impact the mouse gut microbiota promoting colitis and metabolic syndrome. In: Nature . Volume 519, number 7541, 03 2015, pp. 92–96, doi : 10.1038 / nature14232 , PMID 25731162 , PMC 4910713 (free full text).
  9. ↑ Fisher Scientific: Tween® 80

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