Butyl hydroxyanisole

from Wikipedia, the free encyclopedia
Structural formula
Structure of butylated hydroxyanisole
Mixture of two structural isomers
General
Surname Butyl hydroxyanisole
other names
Molecular formula C 11 H 16 O 2
Brief description

white to yellowish, flammable, light-sensitive solid

External identifiers / databases
CAS number
  • 25013-16-5 (mixture of isomers)
EC number 246-563-8
ECHA InfoCard 100.042.315
PubChem 24667
ChemSpider 23068
Wikidata Q409401
properties
Molar mass 180.24 g mol −1
Physical state

firmly

Melting point
  • 48-55 ° C
  • 58-60 ° C
boiling point

268 ° C

solubility

very heavy in water (213 mg l −1 at 25 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning 08 - Dangerous to health 09 - Dangerous for the environment

Caution

H and P phrases H: 315-319-351-361-411
P: 280-301 + 312-305 + 351 + 338-304 + 340-312
MAK

Switzerland: 25 mg m −3 (measured as inhalable dust )

Toxicological data

2000 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 .

Butylhydroxyanisole (BHA, E 320) is a mixture of two structurally isomeric organic chemical compounds from the group of phenol ethers .

use

The mixture is used as a synthetically produced antioxidant . Butylated hydroxyanisole is one of the food additives approved in the EU and may be used in various food categories up to a maximum permitted amount. As a food additive , it prevents rancidity of z. B. nuts and similar snacks, sweets, cake mixes, dry soups or milk powder. However, it is also used in the manufacture of pharmaceuticals and cosmetics .

Analytics

Lipophilic gel chromatography on Sephadex LH 20 can be used to isolate the substance from oils and test materials containing fat . The qualitative and quantitative determination can be carried out by gas chromatography . The coupling of gas chromatography or HPLC with mass spectrometry can also be used for reliable determination.

safety instructions

Ingestion of very large amounts resulted in stomach and liver cancer in mice. There are health concerns because of the triggering of allergies and organic changes in animal experiments.

In 2015, butylated hydroxyanisole was included in the EU's ongoing action plan ( CoRAP ) in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Butylated hydroxyanisole was consumed as a result of concerns about consumer use , exposure of sensitive populations and widespread use, as well as the potential risk from reproductive toxicity and as a potential endocrine disruptor . The re-evaluation has been canceled.

See also

Individual evidence

  1. ↑ Entry on E 320: Butylated hydroxyanisole (BHA) in the European database for food additives, accessed on July 10, 2020.
  2. ↑ Entry on BHA in the CosIng database of the EU Commission, accessed on July 10, 2020.
  3. ↑ a b c d e Entry on tert-butyl-4-methoxyphenol, isomers in the GESTIS substance database of the IFA , accessed on December 30, 2019(JavaScript required) .
  4. ↑ a b c data sheet butylhydroxyanisole at AlfaAesar, accessed on December 30, 2019 ( PDF )(JavaScript required) .
  5. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values , accessed on November 2, 2015.
  6. ↑ Additive Approval Ordinance - ZZulV. Federal Ministry of Justice, March 28, 2011, accessed on June 21, 2011 .
  7. ↑ H.-U. Melchert: Lipophilic gel chromatography for the isolation of BHA and BHT from vegetable oils. In: Chem. Microbiol. Technol. Food 2, 1973, pp. 94-85.
  8. ↑ S. Tsuji, M. Nakanoi, H. Terada, Y. Tamura, Y. Tonogai: Determination and confirmation of five phenolic antioxidants in foods by LC / MS and GC / MS. In: Shokuhin Eiseigaku Zasshi. 46 (3), Jun 2005, pp. 63-71. PMID 16042291
  9. ↑ Hans-Ulrich Grimm: The food trap. How the food industry manipulates our food. 3. Edition. Wilhelm Heyne Verlag, Munich 2010, ISBN 978-3-453-17074-2 .
  10. ↑ Oekotest: Datasheet butylhydroxyanisole ( Memento of 31 January 2003 at the Internet Archive ).
  11. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): tert-butyl-4-methoxyphenol , accessed on March 26, 2019.Template: CoRAP status / 2015