Hydroxyquinol

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Hydroxyquinol
Hydroxyhydrochinon.svg
Names
Preferred IUPAC name
Benzene-1,2,4-triol
Other names
Hydroxyhydroquinone
1,2,4-Benzenetriol
1,2,4-Trihydroxybenzene
Benzene-1,2,4-triol
4-Hydroxycatechol
2,4-Dihydroxyphenol
1,3,4-Benzenetriol
1,3,4-Trihydroxybenzene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.797 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H Yes check.svgY
    Key: GGNQRNBDZQJCCN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H
    Key: GGNQRNBDZQJCCN-UHFFFAOYAX
  • Oc1cc(O)c(O)cc1
Properties
C6H6O3
Molar mass 126.11 g/mol
Appearancewhite solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hydroxyquinol is an organic compound with the formula C6H3(OH)3. It is one of three isomeric benzenetriols. The compound is a colorless solid that is soluble in water. It reacts with air to give a black insoluble solid. [1]

Contents

Production

It is prepared industrially by acetylation of paraquinone with acetic anhydride followed by hydrolysis of the triacetate. [1]

Historically, hydroxyquinol was produced by the action of potassium hydroxide on hydroquinone. [2] It can also be prepared by dehydrating fructose. [3] [4]

C6H12O6 → 3 H2O + C6H6O3

Natural occurrence

Hydroxyquinol is a common intermediate in the biodegradation of many aromatic compounds. These substrates include monochlorophenols, dichlorophenols, and more complex species such as the pesticide 2,4,5-T. [5] Hydroxyquinol commonly occurs in nature as a biodegradation product of catechin, a natural phenol found in plants (e.g. by soil bacteria Bradyrhizobium japonicum ). [6] Hydroxyquinol is also a metabolite in some organisms. For instance, Hydroxyquinol 1,2-dioxygenase is an enzyme that uses hydroxyquinol as a substrate with oxygen to produce 3-hydroxy-cis,cis-muconate.

Related Research Articles

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In chemistry, hydroxylation can refer to:

<span class="mw-page-title-main">Bioremediation</span> Process used to treat contaminated media such as water and soil

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Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.

<span class="mw-page-title-main">Catechin</span> Type of natural phenol as a plant secondary metabolite

Catechin is a flavan-3-ol, a type of secondary metabolite providing antioxidant roles in plants. It belongs to the subgroup of polyphenols called flavonoids.

<span class="mw-page-title-main">Catechol</span> Organic compound (C6H4(OH)2); benzene with two adjacent –OH groups

Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is a toxic organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.

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

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols.

<span class="mw-page-title-main">Azo dye</span> Class of organic compounds used as dye

Azo dyes are organic compounds bearing the functional group R−N=N−R′, in which R and R′ are usually aryl and substituted aryl groups. They are a commercially important family of azo compounds, i.e. compounds containing the C-N=N-C linkage. Azo dyes are synthetic dyes and do not occur naturally. Most azo dyes contain only one azo group, but some dyes contain two or three azo groups, called "diazo dyes" and "triazo dyes" respectively. Azo dyes comprise 60-70% of all dyes used in food and textile industries. Azo dyes are widely used to treat textiles, leather articles, and some foods. Chemically related derivatives of azo dyes include azo pigments, which are insoluble in water and other solvents.

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4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself.

<span class="mw-page-title-main">4-Hydroxyphenylacetate 3-monooxygenase</span>

4-hydroxyphenylacetate 3-monooxygenase (EC 1.14.14.9) is an enzyme that catalyzes the chemical reaction

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<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.

3-Carboxy-<i>cis</i>,<i>cis</i>-muconic acid Chemical compound

3-Carboxy-cis,cis-muconic acid is a metabolite of the catechin degradation by Bradyrhizobium japonicum.

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

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The molecular formula C6H6O5 may refer to:

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

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References

  1. 1 2 Fiege, Helmut; Heinz-Werner, Voges; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2005). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim, Germany: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN   978-3527306732.
  2. Roscoe, Henry (1891). A treatise on chemistry, Volume 3, Part 3. London: Macmillan & Co. p. 199.
  3. Luijkx, Gerard; Rantwijk, Fred; Bekkum, Herman (1993). "Hydrothermal formation of 1,2,4-benzenetriol from 5-hydroxymethyl-2-furaldehyde and D-fructose". Carbohydrate Research. 242 (1): 131–139. doi:10.1016/0008-6215(93)80027-C.
  4. Srokol, Zbigniew; Anne-Gaëlle, Bouche; Estrik, Anton; Strik, Rob; Maschmeyer, Thomas; Peters, Joop (2004). "Hydrothermal upgrading of biomass to biofuel; studies on some monosaccharide model compounds". Carbohydrate Research. 339 (10): 1717–1726. doi:10.1016/j.carres.2004.04.018. PMID   15220081.
  5. Travkin, Vasili M.; Solyanikova, Inna P.; Golovleva, Ludmila A. (2006). "Hydroxyquinol pathway for microbial degradation of halogenated aromatic compounds". Journal of Environmental Science and Health, Part B. 41 (8): 1361–1382. doi:10.1080/03601230600964159. PMID   17090498. S2CID   36347319.
  6. Mahadevan, A.; Waheeta, Hopper (1997). "Degradation of catechin by Bradyrhizobium japonicum". Biodegradation. 8 (3): 159–165. doi:10.1023/A:1008254812074. S2CID   41221044.