丁基羟基茴香醚

「E320」重定向至此。关于欧洲之星集团的一款高速电力动车组型号，请见「英国铁路374型电力动车组」。
丁基羟基茴香醚
IUPAC名
2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole (mixture)
别名 BOA; tert-Butyl-4-hydroxyanisole; (1,1-Dimethylethyl)-4-methoxyphenol; tert-Butyl-4-methoxyphenol; Antioxyne B [1]
识别
CAS号 25013-16-5  checkY
PubChem 24667
ChemSpider 23068
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
InChIKey CZBZUDVBLSSABA-UHFFFAOYAZ
ChEBI 76359
性质
化学式 C11H16O2
摩尔质量 180.24 g·mol−1
外观 蜡状固体
密度 1.0587 g/cm³（20 °C）
熔点 48-55 °C（321-328 K）
沸点 264-270 °C（537-543 K）
溶解性（水） 不溶
溶解性 与乙醇、甲醇, 1,2-丙二醇混溶
可溶于油脂
折光度n
D 		1.5303 @ 589.3nm [2]
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

丁基羟基茴香醚（英語：Butylated hydroxyanisole，简称BHA）是一种抗氧化剂，为两种同分异构体2-叔丁基-4-羟基茴香醚和3-叔丁基-4-羟基茴香醚的混合物，E编码是E320。它是通过对羟基茴香醚与叔丁醇（或异丁烯），或者2-叔丁基对苯二酚与硫酸二甲酯反应合成的。BHA的主要用途是在食品（包括动物食品）、食品包装、化妆品和石油产品中起到抗氧化剂和防腐剂作用。[3] 除此之外，它还被用于药物的抗氧化，如异维甲酸、辛伐他汀等。

抗氧化性质

自1947年，BHA开始被用在可食用脂肪和含脂肪的食品以防止它们的酸败。[4] 像2,6-二叔丁基對甲酚（BHT）一样，BHA的共轭芳香环能够与自由基发生反应，使它们稳定化并消除它们，从而起到了脱氧剂的作用了，减缓了氧化反应的发生。

争议

关于BHA的争议主要集中在它在食品中的使用。美国国家卫生研究院的研究报告认为，基于BHA在实验动物中的致癌性，BHA是一种可疑人类致癌物。在实验中，食物中加入的高剂量BHA使大鼠和叙利亚地鼠患上了前胃处的乳头状瘤和鳞状细胞癌；不过BHA并没有显示出对小鼠的致癌性，而且甚至在一些其他动物中呈现了对其他化学物质的致癌性的保护作用。[4][5]

在BHA对人类的致癌性的调查中，统计显示日常的低量摄入与癌症风险并没有什么联系。[6] 然而有些机构（如加利福尼亚州有关部门）仍将BHA列为人类致癌物。[7]

另见

参考资料

  1. ^ BHA and BHT. [2009-11-20]. （原始内容存档于2009-10-31）. 
  2. ^ SciFinder — Experimental properties for 121-00-6. [2009-11-20]. （原始内容存档于2000-11-09）. 
  3. ^ Hazardous Substances Database （页面存档备份，存于互联网档案馆）, National Library of Medicine
  4. ^ 4.0 4.1 Lam, L. K., R. P. Pai and L. W. Wattenberg. Synthesis and chemical carcinogen inhibitory activity of 2-tert-butyl-4-hydroxyanisole. J Med Chem. 1979, 22 (5): 569–71. PMID 458807. doi:10.1021/jm00191a020. 
  5. ^ Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5 （页面存档备份，存于互联网档案馆）, Report on Carcinogens, Eleventh Edition, National Institutes of Health
  6. ^ 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 (7): 599–605. PMID 10942321. doi:10.1016/S0278-6915(00)00042-9. 
  7. ^ Known Carcinogens and Reproductive Toxicants (California Proposition 65). Scorecard. [2011-05-29]. （原始内容存档于2019-08-14）. 

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