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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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">Food additive</span> Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of ultra-processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose required to kill half the members of a tested population after a specified test duration. LD50 figures are frequently used as a general indicator of a substance's acute toxicity. A lower LD50 is indicative of higher toxicity.

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

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

Butylated hydroxytoluene (BHT), also known as dibutylhydroxytoluene, is a lipophilic organic compound, chemically a derivative of phenol, that is useful for its antioxidant properties. BHT is widely used to prevent free radical-mediated oxidation in fluids and other materials, and the regulations overseen by the U.S. F.D.A.—which considers BHT to be "generally recognized as safe"—allow small amounts to be added to foods. Despite this, and the earlier determination by the National Cancer Institute that BHT was noncarcinogenic in an animal model, societal concerns over its broad use have been expressed. BHT has also been postulated as an antiviral drug, but as of December 2022, use of BHT as a drug is not supported by the scientific literature and it has not been approved by any drug regulatory agency for use as an antiviral.

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

Butylated hydroxyanisole (BHA) is a synthetic, waxy, solid petrochemical. Its antioxidant properties have caused it to be widely used as a preservative in food, food packaging, animal feed, cosmetics, pharmaceuticals, rubber, and petroleum products. BHA has been used in food since around 1947.

<span class="mw-page-title-main">Food coloring</span> Substance used to color to food or drink

Food coloring, or color additive, is any dye, pigment, or substance that imparts color when it is added to food or drink. They can be supplied as liquids, powders, gels, or pastes. Food coloring is used in both commercial food production and domestic cooking. Food colorants are also used in a variety of non-food applications, including cosmetics, pharmaceuticals, home craft projects, and medical devices. Colorings may be natural or artificial/synthetic.

Rancidification is the process of complete or incomplete autoxidation or hydrolysis of fats and oils when exposed to air, light, moisture, or bacterial action, producing short-chain aldehydes, ketones and free fatty acids.

<span class="mw-page-title-main">Quinoline Yellow WS</span> "Mixture of water-soluble organic compounds from Quinoline Yellow dye"

Quinoline Yellow WS is a mixture of organic compounds derived from the dye Quinoline Yellow SS. Owing to the presence of sulfonate groups, the WS dyes are water-soluble (WS). It is a mixture of disulfonates (principally), monosulfonates and trisulfonates of 2-(2-quinolyl)indan-1,3-dione with a maximum absorption wavelength of 416 nm.p. 119

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<span class="mw-page-title-main">Liquid smoke</span> Edible chemical compound

Liquid smoke is a water-soluble yellow to red liquid used as a flavoring as a substitute for cooking with wood smoke while retaining a similar flavor. It can be used to flavor any meat or vegetable. It is available as pure condensed smoke from various types of wood, and as derivative formulas containing additives.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

Isobutylene is a hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.

<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.

<span class="mw-page-title-main">Erythrosine</span> Iodo-derivative of fluorone used as a pink dye

Erythrosine, also known as Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is a pink dye which is primarily used for food coloring. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation.

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

Triacetin is the organic compound with the formula C3H5(OCOCH3)3. It is classified as a triglyceride, i.e., the triester of glycerol with acetic acid. It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations. It is one of the glycerine acetate compounds.

<span class="mw-page-title-main">Allura Red AC</span> Chemical compound

Allura Red AC is a red azo dye that goes by several names, including FD&C Red 40. It is used as a food dye and has the E number E129.

<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

Propyl gallate, or propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol. Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation. As a food additive, it is used under the E number E310.

<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.

Camlin Fine Sciences Ltd., formerly known as Camlin Fine Chemicals, is an Indian corporation that manufactures chemicals to improve the shelf life of food and other products, aromatic compounds, and performance chemicals. CFS has emerged as the largest producer of food antioxidants such as tert-Butylhydroquinone (TBHQ) and Butylated hydroxyanisole (BHA). It is also one of the world's leading Vanillin producers.

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. 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 . Oxford University Press. 14 (1): 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.