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Butylated hydroxyanisole

From Wikipedia, the free encyclopedia
Butylated hydroxyanisole
Names
Preferred IUPAC name
2-tert-Butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol (mixture)
Other names
  • 2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole (mixture)
  • BOA
  • BHA
  • tert-Butyl-4-hydroxyanisole
  • (1,1-Dimethylethyl)-4-methoxyphenol
  • tert-Butyl-4-methoxyphenol
  • Antioxyne B[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.042.315 Edit this at Wikidata
E number E320 (antioxidants, ...)
UNII
  • InChI=1S/2C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12;1-11(2,3)9-7-8(12)5-6-10(9)13-4/h2*5-7,12H,1-4H3 checkY
    Key: CZBZUDVBLSSABA-UHFFFAOYSA-N checkY
  • InChI=1/2C11H16O2/c1-11(2,3)9-7-8(13-4)5-6-10(9)12;1-11(2,3)9-7-8(12)5-6-10(9)13-4/h2*5-7,12H,1-4H3
    Key: CZBZUDVBLSSABA-UHFFFAOYAZ
  • O(c1ccc(O)cc1C(C)(C)C)C.O(c1ccc(O)c(c1)C(C)(C)C)C
Properties
C11H16O2
Molar mass 180.247 g/mol
Appearance Waxy solid
Density 1.0587 g/cm3 at 20 °C
Melting point 48 to 55 °C (118 to 131 °F; 321 to 328 K)
Boiling point 264 to 270 °C (507 to 518 °F; 537 to 543 K)
Insoluble in water
Solubility Freely soluble in ethanol, methanol, propylene glycol; soluble in fats and oils
1.5303 at 589.3 nm[2]
Related compounds
Related compounds
 Butylated hydroxytoluene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Butylated hydroxyanisole (BHA) is a synthetic, waxy, solid petrochemical. Its antioxidant properties have caused it to be widely used as a preservative in food, food packaging, animal feed, cosmetics, pharmaceuticals, rubber, and petroleum products.[3] BHA has been used in food since around 1947.[4]

Chemistry

[edit]

BHA consists of a mixture of two isomeric organic compounds, 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. It is prepared from 4-methoxyphenol and isobutylene.

The conjugated aromatic ring of BHA is able to stabilize free radicals, sequestering them. By acting as free radical scavengers, further free radical reactions are prevented.

Applications

[edit]

Since 1947, BHA has been added to edible fats and fat-containing foods for its antioxidant properties as it prevents rancidification of food which creates objectionable odors.[5] It has been assigned the E number E320. It is often combined with a similar chemical, butylated hydroxytoluene (BHT).[4]

BHA also is commonly used in medicines, such as cholecalciferol (vitamin D3), isotretinoin, lovastatin, and simvastatin, among others.

Health Effects

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The U.S. National Institutes of Health report that BHA is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. In particular, when administered in high doses as part of their diet, BHA causes papillomas and squamous cell carcinomas of the forestomach in rats and Syrian golden hamsters.[6] In mice, there is no carcinogenic effect;[6] in fact, there is evidence of a protective effect against the carcinogenicity of other chemicals.[5]

When examining human population statistics, the usual low intake levels of BHA show no significant association with an increased risk of cancer.[7] The state of California has, however, listed BHA as a carcinogen.[8]

The European Commission has conducted an evaluation of literature. They noted the lack of potential for the compound to induce carcinogenic effects in humans; studies showing carcinogenic effects in hamsters are not relevant to humans (which lack a forestomach). Also noted is that endocrine disruption, if any, is only likely to be present at levels vastly exceeding the intake as a food. [9]

The International Agency for Research on Cancer (IARC) – Summaries & Evaluations stated butylated hydroxyanisole was tested for carcinogenicity in two experiments in rats and in two experiments in hamsters by administration in the diet, inducing benign and malignant tumours of the forestomach. [10]

One of its metabolites is TBHQ (t-butylhydroquinone), a preservative made infamous by food writer Michael Pollan.[4]

See also

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References

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  1. ^ "BHA and BHT". Archived from the original on October 31, 2009. Retrieved Nov 20, 2009.
  2. ^ "SciFinder — Experimental properties for 121-00-6". Retrieved Nov 20, 2009.
  3. ^ Hazardous Substances Database, National Library of Medicine
  4. ^ a b c "BHA and BHT: A Case for Fresh?". Scientific American. December 19, 2013. Retrieved 27 December 2022.
  5. ^ a b Lam, L. K.; R. P. Pai & L. W. Wattenberg (1979). "Synthesis and chemical carcinogen inhibitory activity of 2-tert-butyl-4-hydroxyanisole". J Med Chem. 22 (5): 569–71. doi:10.1021/jm00191a020. PMID 458807.
  6. ^ a b Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5 Archived 2010-06-05 at the Wayback Machine, Report on Carcinogens, Eleventh Edition, National Institutes of Health
  7. ^ Botterweck AAM, Vergaen H, GoldBohm RA, KleinJans J, van den Brant PA (2007). "Intake of Butylated Hydroxyanisole and Butylated Hydroxytoluene and Stomach Cancer Risk: Results from Analyses in the Netherlands Cohort Study". Food and Chemical Toxicology. 38 (7): 599–605. doi:10.1016/S0278-6915(00)00042-9. PMID 10942321.
  8. ^ "Known Carcinogens and Reproductive Toxicants (California Proposition 65)". Scorecard. Archived from the original on 2019-08-14. Retrieved 2011-05-29.
  9. ^ "Scientific Opinion on the re-evaluation of butylated hydroxyanisole - BHA (E 320) as a food additive". EFSA Journal. 9 (10): 2392. 2011. doi:10.2903/j.efsa.2011.2392.
  10. ^ "Butylated Hydroxyanisole (BHA) (IARC Summary & Evaluation, Volume 40, 1986)". inchem.org. Retrieved 2022-01-30.
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