Butylated hydroxyanisole

Last updated
Butylated hydroxyanisole
2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole 2D.svg
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 OOjs UI icon edit-ltr-progressive.svg
E number E320 (antioxidants, ...)
PubChem CID
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 Yes check.svgY
    Key: CZBZUDVBLSSABA-UHFFFAOYSA-N Yes check.svgY
  • 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
AppearanceWaxy 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).
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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]

Contents

Chemistry

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

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

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 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. [8]

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. [9]

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

See also

Related Research Articles

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<span class="mw-page-title-main">Butylated hydroxytoluene</span> Chemical compound

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

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<span class="mw-page-title-main">Ethoxyquin</span> Chemical compound

Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest. It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments.

<span class="mw-page-title-main">Propyl gallate</span> Chemical compound

Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, is an ester formed by the condensation of gallic acid and propanol. Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation. As a food additive, it is used under the E number E310.

<i>tert</i>-Butylhydroquinone Chemical compound

tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

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<span class="mw-page-title-main">Octyl gallate</span> Chemical compound

Octyl gallate is the ester of 1-octanol and gallic acid. As a food additive, it is used under the E number E311 as an antioxidant and preservative.

<span class="mw-page-title-main">Musk xylene</span> Chemical compound

Musk xylene is a synthetic musk fragrance which mimics natural musk. It has been used as a perfume fixative in a wide variety of consumer products, and is still used in some cosmetics and fragrances.

Warmed-over flavor is an unpleasant characteristic usually associated with meat which has been cooked and then refrigerated. The deterioration of meat flavor is most noticeable upon reheating. As cooking and subsequent refrigeration is the case with most convenience foods containing meat, it is a significant challenge to the processed food industry. The flavor is variously described as "rancid," "stale," and like "cardboard," and even compared to "damp dog hair." Warmed-over flavor is caused by the oxidative decomposition of lipids in the meat into chemicals which have an unpleasant taste or odor. This decomposition process begins after cooking or processing and is aided by the release of naturally occurring iron in the meat.

<span class="mw-page-title-main">2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine</span> Chemical compound


PhIP (2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine) is one of the most abundant heterocyclic amines (HCAs) in cooked meat. PhIP is formed at high temperatures from the reaction between creatine or creatinine, amino acids, and sugar. PhIP formation increases with the temperature and duration of cooking and also depends on the method of cooking and the variety of meat being cooked. The U.S. Department of Health and Human Services National Toxicology Program has declared PhIP as "reasonably anticipated to be a human carcinogen". International Agency for Research on Cancer (IARC), part of World Health Organization, has classified PhIP as IARC Group 2B carcinogen. There is sufficient evidence in experimental animals, as well as in vitro models, for the carcinogenicity of PhIP.

Camlin Fine Sciences Ltd., formerly known as Camlin Fine Chemicals, is an Indian corporation that manufactures chemicals to improve the shelf life of food and other products, aromatic compounds, and performance chemicals. CFS has emerged as the largest producer of food antioxidants such as tert-Butylhydroquinone (TBHQ) and Butylated hydroxyanisole (BHA). It is also one of the world's leading Vanillin producers.

References

  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. 1 2 3 "BHA and BHT: A Case for Fresh?". Scientific American. December 19, 2013. Retrieved 27 December 2022.
  5. 1 2 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. 1 2 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. "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 .
  9. "Butylated Hydroxyanisole (BHA) (IARC Summary & Evaluation, Volume 40, 1986)". inchem.org. Retrieved 2022-01-30.