Butylated hydroxyanisole

From Infogalactic: the planetary knowledge core
Jump to: navigation, search

<templatestyles src="Module:Hatnote/styles.css"></templatestyles>

"E320" redirects here. For the high speed train, see British Rail Class 374.
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 N
9009-68-1 N
121-00-6 N
88-32-4 N
ChEBI CHEBI:76359 N
ChEMBL ChEMBL502074 N
ChemSpider 23068 YesY
Jmol 3D model Interactive image
PubChem 24667
UNII REK4960K2U YesY
  • 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 YesY
    Key: CZBZUDVBLSSABA-UHFFFAOYSA-N YesY
  • 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 180.25 g·mol−1
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 589.3nm [2]
Vapor pressure {{{value}}}
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 YesYN ?)
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

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

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 show no significant association with an increased risk of cancer.[6] The State of California, has, however, listed it as a carcinogen.[7]

See also

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Hazardous Substances Database, National Library of Medicine
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5, Report on Carcinogens, Eleventh Edition, National Institutes of Health
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
Retrieved from "https://infogalactic.com/w/index.php?title=Butylated_hydroxyanisole&oldid=56252"