| Revision as of 10:32, 30 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: {{cascite}} StdInChI StdInChIKey.← Previous edit |
Latest revision as of 22:09, 9 December 2024 edit undo176.88.39.125 (talk) →Health Effects: prop 65 isnot reliableTag: references removed |
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{{redirect|E320|the Eurostar/Siemens high speed train|Siemens_Velaro#Eurostar_e320 }} |
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{{chembox |
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| verifiedrevid = 387913823 |
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| ImageFile =BHA2.png |
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| verifiedrevid = 399698891 |
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| ImageSize = |
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| IUPACName = 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole (mixture) |
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| ImageFile = 2-tert-Butyl-4-hydroxyanisole_and_3-tert-butyl-4-hydroxyanisole_2D.svg |
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| OtherNames = BOA |
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| ImageSize = |
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| PIN = 2-''tert''-Butyl-4-methoxyphenol and 3-''tert''-butyl-4-methoxyphenol (mixture)<!-- no substitution on anisole for PINs --> |
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tert-butyl-4-hydroxyanisole |
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| OtherNames = {{ubl |
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(1,1-dimethylethyl)-4-methoxyphenol |
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| 2-''tert''-Butyl-4-hydroxyanisole and 3-''tert''-butyl-4-hydroxyanisole (mixture) |
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tert-butyl-4-methoxyphenol |
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| BOA |
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antioxyne B <ref name='About Chemistry'> {{cite web|url=http://chemistry.about.com/od/foodcookingchemistry/a/bha-bht-preservatives.htm|title=BHA and BHT|accessdate=Nov. 20, 2009 }}</ref> |
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| BHA |
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| ''tert''-Butyl-4-hydroxyanisole |
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| (1,1-Dimethylethyl)-4-methoxyphenol |
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| ''tert''-Butyl-4-methoxyphenol |
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| Antioxyne B<ref name=AboutChemistry>{{cite web|url=http://chemistry.about.com/od/foodcookingchemistry/a/bha-bht-preservatives.htm|title=BHA and BHT|access-date=Nov 20, 2009|archive-date=October 31, 2009|archive-url=https://web.archive.org/web/20091031131459/http://chemistry.about.com/od/foodcookingchemistry/a/bha-bht-preservatives.htm|url-status=dead}}</ref> |
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}} |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 23068 |
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| ChemSpiderID = 23068 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 76359 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 502074 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = REK4960K2U |
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| UNII = REK4960K2U |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = A03IJ8ROOP |
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| UNII1_Comment = (''2-tert'') |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = 62RAC24292 |
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| UNII2_Comment = (''3-tert'') |
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| 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 |
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| 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 |
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| InChIKey = CZBZUDVBLSSABA-UHFFFAOYAZ |
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| InChIKey = CZBZUDVBLSSABA-UHFFFAOYAZ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CZBZUDVBLSSABA-UHFFFAOYSA-N |
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| StdInChIKey = CZBZUDVBLSSABA-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 25013-16-5 |
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| CASNo = 25013-16-5 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASOther = 8003-24-5, 9009-68-1, 121-00-6, 88-32-4 |
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| PubChem = 24667 |
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| CASNo2 = 121-00-6 |
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| CASNo2_Comment = (''2-tert'') |
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| SMILES = O(c1ccc(O)cc1C(C)(C)C)C.O(c1ccc(O)c(c1)C(C)(C)C)C |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| CASNo3 = 88-32-4 |
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| CASNo3_Comment = (''3-tert'') |
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| PubChem = 24667 |
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| SMILES1 = O(c1ccc(O)cc1C(C)(C)C)C.O(c1ccc(O)c(c1)C(C)(C)C)C |
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}} |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=11|H=16|O=2 |
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| Formula = C<sub>11</sub>H<sub>16</sub>O<sub>2</sub> |
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| MolarMass = 180.24 g/mol |
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| MolarMassUnit = g/mol |
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| Appearance = waxy solid |
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| Appearance = Waxy solid |
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| Density = 1.0587 g/cm³ at 20°C |
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| Density = 1.0587{{nbsp}}g/cm<sup>3</sup> at 20{{nbsp}}°C |
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| MeltingPt = 48-55 °C |
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| MeltingPtC = 48 to 55 |
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| BoilingPt = 264-270 °C |
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| BoilingPtC = 264 to 270 |
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| Solubility = Insoluble in water; freely soluble in ethanol, methanol, propylene glycol; soluble in fats and oils |
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| Solubility = Insoluble in water |
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| SolubleOther = Freely soluble in ], ], ]; soluble in fats and oils |
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| RefractIndex = 1.5303 at 589.3nm <ref name='Scifinder'> {{cite web|url=https://scifinder.cas.org |title=SciFinder — Experimental properties for 121-00-6|accessdate=Nov. 20, 2009 }}</ref> |
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| RefractIndex = 1.5303 at 589.3{{nbsp}}nm<ref name='Scifinder'>{{cite web|url=https://scifinder.cas.org |title=SciFinder — Experimental properties for 121-00-6|access-date=Nov 20, 2009 }}</ref> |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| Section 4 = {{Chembox Related |
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| Section4 = {{Chembox Related |
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| OtherCpds = ] |
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| OtherCompounds = ] |
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'''Butylated hydroxyanisole''' ('''BHA''') is an ] consisting of a mixture of two ]ic organic compounds, 2-''tert''-butyl-4-hydroxyanisole and 3-''tert''-butyl-4-hydroxyanisole. It is prepared from ] and ]. It is a waxy solid used in certain amounts as a ] with the ] E320. The primary use for BHA is as an antioxidant and preservative in food, food packaging, animal feed, and cosmetics, and in rubber and petroleum products.<ref>HSDB. 2000. Hazardous Substances Data Base. National Library of Medicine. http://toxnet.nlm.nih.gov/ |
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cgi-bin/sis/htmlgen?HSDB.</ref> BHA also is commonly used in medicines, such as ] (known as Accutane/Roaccutane), ], and ], among others. |
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'''Butylated hydroxyanisole''' ('''BHA''') is a synthetic, waxy, solid ]. Its ] properties have caused it to be widely used as a preservative in food, food packaging, animal feed, cosmetics, pharmaceuticals, rubber, and petroleum products.<ref>, National Library of Medicine</ref> BHA has been used in food since around 1947.<ref name="SA">{{cite news |title=BHA and BHT: A Case for Fresh? |url=https://www.scientificamerican.com/article/bha-and-bht-a-case-for-fresh/ |access-date=27 December 2022 |work=Scientific American |date=December 19, 2013}}</ref> |
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==Antioxidant Properties== |
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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.<ref>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.</ref> Like ] (BHT), the conjugated aromatic ring of BHA is able to stabilize ]s, sequestering them. By acting as free radical ]s, further free radical reactions are prevented. |
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==Carcinogenicity== |
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==Chemistry== |
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BHA consists of a mixture of two ]ic organic compounds, 2-''tert''-butyl-4-hydroxyanisole and 3-''tert''-butyl-4-hydroxyanisole. It is prepared from ] and ]. |
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Some controversy surrounds the use of BHA in foods. The US ] report that BHA is reasonably anticipated to be a human carcinogen based on evidence of carcinogenicity in experimental animals. In particular, when administered as part of their diet, BHA causes ] and ] of the forestomach in rats and Syrian golden ].<ref>Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5, Report on Carcinogens, Eleventh Edition, National Institutes of Health, http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s027bha.pdf</ref> That said, when examining human population statistics, the usual low intake levels of BHA shows no significant association with an increased risk of cancer.<ref>Botterweck AAM, Vergaen H, GoldBohm RA, KleinJans J, van den Brant PA "Intake of Butylated Hydroxyanisole and Butylated Hydroxytoluene and Stomach Cancer Risk: Results from Analyses in the Netherlands Cohort Study", Food and Chemical Toxicology. 2007;38:599-605.</ref> The State of California, has, however, listed it as a carcinogen. Furthermore, the acceptable daily intake (ADI) of BHA and a similar preservative, ] BHT, is exceeded by only a small fraction of the population.<ref>Soubra L, Sarkis D, Hilan C, Verger Ph, "Dietary exposure of children and teenages to benzoates, sulphites, butylhydroxyanisol, (BHA) and butylhydroxytoluen (BHT) in Beirut (Lebanon)", Regulatory Toxicology and Pharmacology. 2007;47:68-77.</ref> |
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The conjugated aromatic ring of BHA is able to stabilize ]s, sequestering them. By acting as free radical ]s, further free radical reactions are prevented. |
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==Applications== |
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Since 1947, BHA has been added to edible fats and fat-containing foods for its antioxidant properties as it prevents ] of food which creates objectionable odors.<ref name=Lam>{{cite journal | doi = 10.1021/jm00191a020 | author = Lam, L. K. | author2 = R. P. Pai | author3 = L. W. Wattenberg | name-list-style = amp | year = 1979 | title = Synthesis and chemical carcinogen inhibitory activity of 2-''tert''-butyl-4-hydroxyanisole | journal = J Med Chem | volume = 22 | issue = 5 | pages = 569–71 | pmid = 458807}}</ref> It has been assigned the ] E320. It is often combined with a similar chemical, ] (BHT).<ref name="SA"/> |
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BHA also is commonly used in medicines, such as ] (vitamin D<sub>3</sub>), ], ], and ], among others. |
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==Health effects== |
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The U.S. ] report that BHA is reasonably anticipated to be a human ] based on evidence of carcinogenicity in experimental animals. In particular, when administered in high doses as part of their diet, BHA causes ]s and ]s of the forestomach in rats and Syrian golden ]s.<ref name=ROC> {{Webarchive|url=https://web.archive.org/web/20100605124129/http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s027bha.pdf# |date=2010-06-05 }}, ''Report on Carcinogens'', Eleventh Edition, ]</ref> In mice, there is no carcinogenic effect;<ref name=ROC/> in fact, there is evidence of a protective effect against the carcinogenicity of other chemicals.<ref name=Lam/> |
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When examining human ], the usual low intake levels of BHA show no significant association with an increased risk of cancer.<ref>{{cite journal | doi = 10.1016/S0278-6915(00)00042-9 | vauthors = ((Botterweck AAM)), Vergaen H, GoldBohm RA, KleinJans J, van den Brant PA | title = Intake of Butylated Hydroxyanisole and Butylated Hydroxytoluene and Stomach Cancer Risk: Results from Analyses in the Netherlands Cohort Study | journal = ] | year = 2007 | volume = 38 | issue = 7 | pages = 599–605 | pmid = 10942321| url = https://cris.maastrichtuniversity.nl/portal/en/publications/intake-of-butylated-hydroxyanisole-and-butylated-hydroxytoluene-and-stomach-cancer-risk-results-from-analyses-in-the-netherlands-cohort-study(7abde0bd-1682-4da8-8ebf-b8373b7ed481).html }}</ref> |
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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. <ref>{{cite journal |doi=10.2903/j.efsa.2011.2392|title=Scientific Opinion on the re-evaluation of butylated hydroxyanisole - BHA (E 320) as a food additive|journal=EFSA Journal|year=2011|volume=9|issue=10|page=2392|doi-access=free}}</ref> |
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The ] – 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. <ref>{{Cite web|title=Butylated Hydroxyanisole (BHA) (IARC Summary & Evaluation, Volume 40, 1986)|url=https://inchem.org/documents/iarc/vol40/butylatedhydroxyanisole.html|access-date=2022-01-30|website=inchem.org}}</ref> |
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One of its metabolites is ] (''t''-butylhydroquinone), a preservative made infamous by food writer ].<ref name="SA"/> |
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== See also == |
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== See also == |
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