Butylated hydroxyanisole TENOX

From Wikipedia, the free encyclopedia

Jump to: navigation, search
"E320" redirects here. For the high speed train, see Siemens_Velaro#Eurostar_e320 .

Butylated hydroxyanisole

IUPAC name[hide]
2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4hydroxyanisole (mixture)
Other names[hide]
BOA; tert-Butyl-4-hydroxyanisole; (1,1-Dimethylethyl)-4methoxyphenol; tert-Butyl-4-methoxyphenol; Antioxyne B [1]
Identifiers
25013-16-5 , 8003-24-5, 9009-68-1, 121-00CAS number
6, 88-32-4
PubChem
24667
ChemSpider 23068
UNII
REK4960K2U
ChEMBL
CHEMBL502074
Jmol-3D
Image 1
images
SMILES
[show]
InChI
[show]
Properties
Molecular
C11H16O2
formula
Molar mass
180.24 g mol1
Appearance
waxy solid
Density
1.0587 g/cm at 20 C
Melting point
Boiling point
Solubility in
water
Refractive

48-55 C, 321-328 K, 118-131 F

264-270 C, 537-543 K, 507-518 F
Insoluble in water; freely soluble in ethanol,
methanol, propylene glycol; soluble in fats
and oils
1.5303 at 589.3nm [2]

index (nD)
(verify) (what is: / ?)
Except where noted otherwise, data are given for materials in
their standard state (at 25 C, 100 kPa)
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-4hydroxyanisole. 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.

Contents
[hide]

1 Antioxidant properties
2 Controversy
3 See also

4 References

[edit] Antioxidant properties

Since 1947, BHA has been added to edible fats and fat-containing foods for its
antioxidant properties as it prevents food from becoming rancid and developing
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.

[edit] Controversy
Some controversy surrounds the use of BHA in foods. The US 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]

[edit] See also

Anisole
Butylated hydroxytoluene (BHT)

[edit] References
1.
2.
3.
4.
5.
6.

7.

^ "BHA and BHT".

http://chemistry.about.com/od/foodcookingchemistry/a/bha-bht-preservatives.htm.
Retrieved Nov. 20, 2009.
^ "SciFinder Experimental properties for 121-00-6".
https://scifinder.cas.org. Retrieved Nov. 20, 2009.
^ Hazardous Substances Database, National Library of Medicine
^ 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): 56971. doi:10.1021/jm00191a020. PMID 458807.
^ a b Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5, Report on
Carcinogens, Eleventh Edition, National Institutes of Health
^ 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): 599605.
doi:10.1016/S0278-6915(00)00042-9. PMID 10942321.
^ "Known Carcinogens and Reproductive Toxicants (California
Proposition 65)". Scorecard. http://scorecard.goodguide.com/chemicalgroups/one-list.tcl?short_list_name=p65. Retrieved 2011-05-29.