Butylated hydroxyanisole

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Butylated hydroxyanisole
2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole 2D.svg
Names
IUPAC name
2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole (mixture)
Other names
BOA; BHA; tert-Butyl-4-hydroxyanisole; (1,1-Dimethylethyl)-4-methoxyphenol; tert-Butyl-4-methoxyphenol; Antioxyne B [1]
Identifiers
25013-16-5 YesY
8003-24-5, 9009-68-1, 121-00-6, 88-32-4
ChEBI CHEBI:76359 N
ChEMBL ChEMBL502074 N
ChemSpider 23068 YesY
Jmol-3D images Image
PubChem 24667
UNII REK4960K2U YesY
Properties
C11H16O2
Molar mass 180.24 g·mol−1
Appearance waxy solid
Density 1.0587 g/cm³ at 20 °C
Melting point 48 °C (118 °F; 321 K)
Boiling point 264 °C (507 °F; 537 K)
Insoluble in water
Solubility freely soluble in ethanol, methanol, propylene glycol; soluble in fats and oils
1.5303 at 589.3nm [2]
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

Butylated hydroxyanisole (BHA) is an antioxidant consisting 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. It is a waxy solid used as a food additive with the E number E320. The primary use for BHA is as an antioxidant and preservative in food, food packaging, animal feed, cosmetics, rubber, and petroleum products.[3] BHA also is commonly used in medicines, such as isotretinoin, lovastatin, and simvastatin, among others.

Antioxidant properties[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.[4] Like butylated hydroxytoluene (BHT), 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.

Research[edit]

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.[5] In mice, there is no carcinogenic effect,[5] and even evidence of a protective effect against the carcinogenicity of other chemicals.[4]

When examining human population statistics, the usual low intake levels of BHA shows no significant association with an increased risk of cancer.[6] The State of California, has, however, listed it as a carcinogen.[7]

See also[edit]

References[edit]

  1. ^ "BHA and BHT". 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 Lam, L. K., R. P. Pai and 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. 
  5. ^ a b Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5, Report on Carcinogens, Eleventh Edition, National Institutes of Health
  6. ^ 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. 
  7. ^ "Known Carcinogens and Reproductive Toxicants (California Proposition 65)". Scorecard. Retrieved 2011-05-29.