Tert-Butylhydroquinone

Last updated
tert-Butylhydroquinone
Tert-Butylhydroquinone-Skeletal.svg
Names
Preferred IUPAC name
2-tert-Butylbenzene-1,4-diol
Other names
TBHQ(i)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.016.139 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-752-2
E number E319 (antioxidants, ...)
PubChem CID
UNII
  • InChI=1S/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3 Yes check.svgY
    Key: BGNXCDMCOKJUMV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H14O2/c1-10(2,3)8-6-7(11)4-5-9(8)12/h4-6,11-12H,1-3H3
    Key: BGNXCDMCOKJUMV-UHFFFAOYAP
  • Oc1ccc(O)cc1C(C)(C)C
Properties
C10H14O2
Molar mass 166.220 g·mol−1
AppearanceTan powder
Density 1.050 g/mL
Melting point 127 to 129 °C (261 to 264 °F; 400 to 402 K)
Boiling point 273 °C (523 °F; 546 K)
Slightly soluble
Acidity (pKa)10.80±0.18
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Harmful
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H312, H315, H317, H319, H335, H400
P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, P403+P233, P405, P501
Flash point 171 °C (340 °F; 444 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
Butylated hydroxyanisole (BHA)
4-tert-Butylcatechol (TBC)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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tert-Butylhydroquinone (TBHQ, tertiary butylhydroquinone) is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

Contents

Applications

Food preservative

In foods, TBHQ is used as a preservative for unsaturated vegetable oils and many edible animal fats. It does not cause discoloration even in the presence of iron, and does not change flavor or odor of the material to which it is added. [1] It can be combined with other preservatives such as butylated hydroxyanisole (BHA). As a food additive, its E number is E319. It is added to a wide range of foods. Its primary advantage is extending storage life. [1]

Other

In perfumery, it is used as a fixative to lower the evaporation rate and improve stability.

It is used industrially as a stabilizer to inhibit autopolymerization of organic peroxides.

It is used as an antioxidant in biodiesel. [2]

It is also added to varnishes, lacquers, resins, and oil-field additives.

Safety and regulation

The European Food Safety Authority (EFSA) and the United States Food and Drug Administration (FDA) [3] have evaluated TBHQ and determined that it is safe to consume at the concentration allowed in foods. [4] The FDA [5] and European Union [4] both set an upper limit of 0.02% (200mg/kg) of the oil or fat content in foods. At very high doses, it has some negative health effects on lab animals, such as producing precursors to stomach tumors and damage to DNA. [6]

A number of studies have shown that prolonged exposure to very high doses of TBHQ may be carcinogenic, [7] especially for stomach tumors. [8] Other studies, however, have shown opposite effects including inhibition against HCA-induced carcinogenesis (by depression of metabolic activation) for TBHQ and other phenolic antioxidants (TBHQ was one of several, and not the most potent). [9] The EFSA considers TBHQ to be noncarcinogenic. [4] A 1986 review of scientific literature concerning the toxicity of TBHQ determined that a wide margin of safety exists between the levels of intake by humans and the doses that produce adverse effects in animal studies. [10]

In addition, TBHQ has been identified by high-throughput screening as having potential immunotoxic effects. [11]

There have been reports of vision disturbances in individuals exposed to this chemical. [12]

Related Research Articles

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<span class="mw-page-title-main">Butylated hydroxyanisole</span> Chemical compound

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<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

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<span class="mw-page-title-main">Propylparaben</span> Chemical compound

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<span class="mw-page-title-main">Ethoxyquin</span> Chemical compound

Ethoxyquin (EMQ) is a quinoline-based antioxidant used as a food preservative in certain countries and originally to control scald on pears after harvest. It is used as a preservative in some pet foods to slow the development of rancidity of fats. Ethoxyquin is also used in some spices to prevent color loss due to oxidation of the natural carotenoid pigments.

<span class="mw-page-title-main">Propyl gallate</span> Chemical compound

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<span class="mw-page-title-main">Protocatechuic acid</span> Chemical compound

Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies. It is produced commercially from vanillin.

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References

  1. 1 2 Fats and oils: formulating and processing for applications, Richard D. O'Brien, page 168
  2. Almeida, Eduardo S.; Portela, Flaysner M.; Sousa, Raquel M.F.; Daniel, Daniela; Terrones, Manuel G.H.; Richter, Eduardo M.; Muñoz, Rodrigo A.A. (2011). "Behaviour of the antioxidant tert-butylhydroquinone on the storage stability and corrosive character of biodiesel". Fuel. 90 (11): 3480–3484. Bibcode:2011Fuel...90.3480A. doi: 10.1016/j.fuel.2011.06.056 .
  3. "Food Additive Status List". U.S. Food and Drug Administration. Retrieved June 11, 2016.
  4. 1 2 3 "Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) on a request from the Commission related to tertiary-Butylhydroquinone (TBHQ)". European Food Safety Authority, 12 July 2004
  5. 21 C.F.R. § 172.185
  6. Tert-Butylhydroquinone - safety summary from The International Programme on Chemical Safety
  7. Gharavi N, El-Kadi A (2005). "tert-Butylhydroquinone is a novel aryl hydrocarbon receptor ligand". Drug Metab Dispos. 33 (3): 365–72. doi:10.1124/dmd.104.002253. PMID   15608132. S2CID   5963778.
  8. Hirose, Masao; Yada, Hideaki; Hakoi, Kazuo; Takahashi, Satoru; Ito, Nobuyuki; et al. (1993). "Modification of carcinogenesis by -tocopherol, t-butylhydro-quinone, propyl gallate and butylated hydroxytoluene in a rat multi-organ carcinogenesis model". Carcinogenesis . 14 (1). Oxford University Press: 2359–2364. doi:10.1093/carcin/14.11.2359. PMID   8242867.
  9. Hirose M, Takahashi S, Ogawa K, Futakuchi M, Shirai T, Shibutani M, Uneyama C, Toyoda K, Iwata H (1999). "Chemoprevention of heterocyclic amine-induced carcinogenesis by phenolic compounds in rats". Cancer Lett. 143 (2): 173–8. doi:10.1016/S0304-3835(99)00120-2. PMID   10503899.
  10. Vanesch, G (1986). "Toxicology of tert-butylhydroquinone (TBHQ)". Food and Chemical Toxicology . 24 (10–11): 1063–5. doi:10.1016/0278-6915(86)90289-9. PMID   3542758.
  11. Naidenko, Olga V.; Andrews, David Q.; Temkin, Alexis M.; Stoiber, Tasha; Uche, Uloma Igara; Evans, Sydney; Perrone-Gray, Sean (2021-03-24). "Investigating Molecular Mechanisms of Immunotoxicity and the Utility of ToxCast for Immunotoxicity Screening of Chemicals Added to Food". International Journal of Environmental Research and Public Health. 18 (7): 3332. doi: 10.3390/ijerph18073332 . ISSN   1660-4601. PMC   8036665 . PMID   33804855.