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introduce the butyl group into a chemical compound

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/04 16:26:57」(JST)

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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 [edit]

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.

Research [edit]

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]

References [edit]

^ "BHA and BHT". Retrieved Nov. 20, 2009.
^ "SciFinder — Experimental properties for 121-00-6". 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): 569–71. 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): 599–605. doi:10.1016/S0278-6915(00)00042-9. PMID 10942321.
^ "Known Carcinogens and Reproductive Toxicants (California Proposition 65)". Scorecard. Retrieved 2011-05-29.

UpToDate Contents

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1. 食品添加物に対するアレルギー反応および喘息反応 allergic and asthmatic reactions to food additives
2. 食品添加物に対するアレルギー反応および喘息反応を評価するための検査法および
チャレンジテスト testing and challenge procedures to evaluate allergic and asthmatic reactions to food additives

English Journal

Spectroscopic studies on the antioxidant activity of ellagic acid.

Kilic I1, Yeşiloğlu Y2, Bayrak Y2.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Sep 15;130:447-52. doi: 10.1016/j.saa.2014.04.052. Epub 2014 May 2.
Ellagic acid (EA, C14H6O8) is a natural dietary polyphenol whose benefits in a variety of diseases shown in epidemiological and experimental studies involve anti-inflammation, anti-proliferation, anti-angiogenesis, anticarcinogenesis and anti-oxidation properties. In vitro radical scavenging and ant
PMID 24813273

Sestrin2 inhibits uncoupling protein 1 expression through suppressing reactive oxygen species.

Ro SH1, Nam M2, Jang I1, Park HW1, Park H1, Semple IA1, Kim M1, Kim JS3, Park H1, Einat P4, Damari G4, Golikov M4, Feinstein E4, Lee JH5.
Proceedings of the National Academy of Sciences of the United States of America.Proc Natl Acad Sci U S A.2014 May 27;111(21):7849-54. doi: 10.1073/pnas.1401787111. Epub 2014 May 13.
Uncoupling protein 1 (Ucp1), which is localized in the mitochondrial inner membrane of mammalian brown adipose tissue (BAT), generates heat by uncoupling oxidative phosphorylation. Upon cold exposure or nutritional abundance, sympathetic neurons stimulate BAT to express Ucp1 to induce energy dissipa
PMID 24825887

Luteolin inhibits the Nrf2 signaling pathway and tumor growth in vivo.

Chian S1, Thapa R1, Chi Z1, Wang XJ2, Tang X3.
Biochemical and biophysical research communications.Biochem Biophys Res Commun.2014 May 16;447(4):602-8. doi: 10.1016/j.bbrc.2014.04.039. Epub 2014 Apr 18.
Nuclear factor erythroid 2-related factor 2 (Nrf2) is over-expressed in many types of tumor, promotes tumor growth, and confers resistance to anticancer therapy. Hence, Nrf2 is regarded as a novel therapeutic target in cancer. Previously, we reported that luteolin is a strong inhibitor of Nrf2 in vi
PMID 24747074

Japanese Journal

Overexpression of Hematopoietically Expressed Homeoprotein Induces Nonapoptotic Cell Death in Mouse Prechondrogenic ATDC5 Cells

Morimoto Riyo,Obinata Akiko
Biological & Pharmaceutical Bulletin 34(10), 1589-1595, 2011
… The expression rate of Hex-EGFP clearly increased by treatment with radical scavengers, propyl gallate and butylated hydroxyanisole, slightly increased with a caspase inhibitor, zVAD-fmk, and was not affected by N-acetyl cysteine in ATDC5 cells. …
NAID 130001086592

Effects of Food Additives on Susceptibility of Gram Negative Bacteria Derived from Dry-Fermented Sausage

DORJ Serjmyadag,SHIMADA Kenichiro,SEKIKAWA Mitsuo
Food science and technology research 15(2), 185-190, 2009-03-01
… The food additives used included synthetic antioxidants (butylated hydroxyanisole, BHA, and butylated hydroxytoluene, BHT), a curing agent and lactic acid with or without a cell-free supernatant (CFS) containing antimicrobial compounds of Lactobacillus sakei D-1001. …
NAID 10025349005

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リンク元	「BHA」「ブチルヒドロキシアニソール」
関連記事	「hydroxyanisole」

「BHA」

Butylated hydroxyanisole
	IUPAC name 2-tert-Butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole (mixture)
	Other names BOA; tert-Butyl-4-hydroxyanisole; (1,1-Dimethylethyl)-4-methoxyphenol; tert-Butyl-4-methoxyphenol; Antioxyne B
Identifiers
CAS number	25013-16-5 , 8003-24-5, 9009-68-1, 121-00-6, 88-32-4
PubChem	24667
ChemSpider	23068
UNII	REK4960K2U
ChEMBL	CHEMBL502074
Jmol-3D images	Image 1
	SMILES O(c1ccc(O)cc1C(C)(C)C)C.O(c1ccc(O)c(c1)C(C)(C)C)C ;
	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/h25-7,12H,1-4H3 ; Key: CZBZUDVBLSSABA-UHFFFAOYSA-N 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/h25-7,12H,1-4H3; Key: CZBZUDVBLSSABA-UHFFFAOYAZ ;
Properties
Molecular formula	C11H16O2
Molar mass	180.24 g mol−1
Appearance	waxy solid
Density	1.0587 g/cm³ at 20 °C
Melting point	48-55 °C, 321-328 K, 118-131 °F
Boiling point	264-270 °C, 537-543 K, 507-518 °F
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
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★] ブチルヒドロキシアニソール butylated hydroxyanisole

「ブチルヒドロキシアニソール」

　　[★]

英: butylated hydroxyanisole、BHA

酸化防止剤

「hydroxyanisole」

　　[★]

ヒドロキシアニソール

[AboutChemistry-1] "BHA and BHT". Retrieved Nov. 20, 2009.

[Scifinder-2] "SciFinder — Experimental properties for 121-00-6". Retrieved Nov. 20, 2009.

[3] Hazardous Substances Database, National Library of Medicine

[Lam-4] 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. doi:10.1021/jm00191a020. PMID 458807.

[ROC-5] Butylated Hydroxyanisole (BHA), CAS No. 25013-16-5, Report on Carcinogens, Eleventh Edition, National Institutes of Health

[6] 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): 599–605. doi:10.1016/S0278-6915(00)00042-9. PMID 10942321.

[7] "Known Carcinogens and Reproductive Toxicants (California Proposition 65)". Scorecard. Retrieved 2011-05-29.

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butylated hydroxyanisole