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Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of Phenols, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two covalent bond to a benzene ring in a para position. It is a white granular solid. Substituted derivatives of this parent compound are also referred to as hydroquinones. The name "hydroquinone" was coined by Friedrich Wöhler in 1843.F. Wöhler (1844) "Untersuchungen über das Chinon" (Investigations of quinone), Annalen der Chemie und Pharmacie, 51 : 145-163. From page 146: "Das so erhaltene Destillat … enthält … einen neuen, krystallisierenden Körper, den ich unter dem Namen farbloses Hydrochinon weiter unten näher beschreiben werde." (The distillate so obtained … contains … a new, crystallizable substance, that I will describe, under the name of colorless hydroquinone, further below in more detail.) Note:
In 2022, it was the 268th most commonly prescribed medication in the United States, with more than 900,000 prescriptions.
Other, less common methods include:
When colorless hydroquinone and benzoquinone - bright yellow in solid form - are at a 1:1 ratio, a dark-green crystalline charge-transfer complex (melting point 171 °C), known as quinhydrone (), is formed. This complex dissolves in hot water, dissociating both quinone molecules in solution.
There are various other uses associated with its reducing agent. As a polymerisation inhibitor, exploiting its antioxidant properties, hydroquinone prevents polymerization of acrylic acid, methyl methacrylate, cyanoacrylate, and other monomers that are susceptible to radical-initiated polymerization. By acting as a free radical scavenger, hydroquinone serves to prolong the shelflife of light-sensitive resins such as preceramic polymers. Additive manufacturing of ceramics from preceramic polymers Additive manufacturing 2019 vol. 27. pp 80-90
Hydroquinone can lose a hydrogen cation from both hydroxyl groups to form a diphenolate ion. The disodium diphenolate salt of hydroquinone is used as an alternating comonomer unit in the production of the polymer PEEK.
In 2006, United States Food and Drug Administration revoked its previous approval of hydroquinone and proposed a ban on all over-the-counter preparations. The FDA officially banned hydroquinone in 2020 as part of a larger reform of the over-the-counter drug review process. The FDA stated that hydroquinone cannot be ruled out as a potential carcinogen. This conclusion was reached based on the extent of absorption in humans and the incidence of in rats in several studies where adult rats were found to have increased rates of tumours, including thyroid follicular cell hyperplasias, anisokaryosis (variation in nuclei sizes), mononuclear cell leukemia, hepatocellular adenomas and kidney cancer. The Campaign for Safe Cosmetics has also highlighted concerns. Campaign For Safe Cosmetics - Hydroquinone
Numerous studies have revealed that hydroquinone, if taken orally, can cause exogenous ochronosis, a disfiguring disease in which blue-black pigments are deposited onto the skin; however, skin preparations containing the ingredient are administered topically. The FDA had classified hydroquinone in 1982 as a safe product - generally recognized as safe and effective (GRASE), however additional studies under the National Toxicology Program (NTP) were suggested in order to determine whether there is a risk to humans from the use of hydroquinone. NTP evaluation showed some evidence of long-term carcinogenic and genotoxic effects.
While hydroquinone remains widely prescribed for treatment of hyperpigmentation, questions raised about its safety profile by regulatory agencies in the EU, Japan, and USA encourage the search for other agents with comparable efficacy. Several such agents are already available or under research, including azelaic acid, kojic acid, retinoids, cysteamine, topical steroids, glycolic acid, and other substances. One of these, 4-butylresorcinol, has been proved to be more effective at treating melanin-related skin disorders by a wide margin, as well as safe enough to be made available over the counter.
In the anthraquinone process substituted hydroquinones, typically anthrahydroquinone are used to produce hydrogen peroxide which forms spontaneously on reaction with oxygen. The type of substituted hydroquinone is selected depending on reactivity and recyclability.
Hydroquinone is thought to be the active toxin in Agaricus hondensis mushrooms.
Hydroquinone has been shown to be one of the chemical constituents of the natural product propolis.
It is also one of the chemical compounds found in castoreum. This compound is gathered from the beaver's castor sacs.The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 ( book at google books)
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