Butylated hydroxyanisole

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
Identifiers
CAS Number	25013-16-5 Y 8003-24-5 N 9009-68-1 N 121-00-6 N 88-32-4 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:76359 N
ChemSpider	23068 Y
ECHA InfoCard	100.042.315
E number	E320 (antioxidants, ...)
PubChem CID	24667
UNII	REK4960K2U Y
InChI 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 Y Key: CZBZUDVBLSSABA-UHFFFAOYSA-N Y 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
SMILES O(c1ccc(O)cc1C(C)(C)C)C.O(c1ccc(O)c(c1)C(C)(C)C)C
Properties
Chemical formula	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)
Solubility in water	Insoluble in water
Solubility	freely soluble in ethanol, methanol, propylene glycol; soluble in fats and oils
Refractive index (nD)	1.5303 at 589.3nm
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  (what is YN ?)
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. BHA also is commonly used in medicines, such as isotretinoin, lovastatin, and simvastatin, among others.

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. 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.

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

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