What group of organic compounds has a hydroxyl group-O-H attached to a carbon atom?

Phenols are organic compounds which comprise a hydroxyl (—OH) group fastened to a carbon atom in a benzene ring.  Their chemic behavior is very distinct from that of alcohols, because they are non capable of undergoing the same oxidation reactions that alcohols participate it.  Besides, different alcohols, phenols are weak acids, since the phenoxide anion generated past the loss of the hydroxyl proton is resonance-stabilized:

Phenols are named afterwards the parent compound, phenol (hydroxybenzene).  When other substituents are present, the carbon bearing the OH grouping is carbon number ane, and the substituents around the band are numbered appropriately.

Phenol	3D
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Phenol, or hydroxybenzene, is the parent compound of the phenols, consisting of an OH grouping directly connected to a benzene ring.  Phenol is the active ingredient in some treatments for sore throats, and is found in several lozenges and throat sprays.  It is used in the industry of many other compounds, such every bit aspirin, and Bakelite. Phenol was also the first compound to be used in antiseptic surgery.  Joseph Lister (1827-1912), an English surgeon at the Glasgow Regal Infirmary, used solutions of phenol dissolved in water, known as carbolic acid, to kill germs in wounds and to sterilize medical equipment, drastically cutting down the number of deaths caused past infections.  In the words of Isaac Asimov, "Eventually chemical less irritating to tissue and even more than effective in killing germs were discovered, simply Lister and his carbolic acrid had founded antiseptic surgery.  Overriding initial resistance to his findings past medical conservatives, he succeeded in converting hospitals into something more than elaborate pauses on the way to the grave." (one) [Listerine, originally formulated past Joseph Lawrence and Hashemite kingdom of jordan Lambert in 1879, as a surgical clarified, was named later Lister.]
two-Phenylphenol	3D
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2-Phenylphenol, or ortho-phenylphenol, is an ingredient in Lysol, and is an agronomical fungicide.
2-Benzyl-4-chlorophenol	3D
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2-Benzyl-4-chlorophenol is an ingredient in Lysol.
ortho-Cresol	3D
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Cresol is a petty name for the three isomeric methylphenols.  The structure shown above is ortho-cresol, or 2-methylphenol; the other isomers are shown below: The cresols are commonly used equally solvents, in disinfectants and deodorizers, and in the manufacture of other compounds (for example, the BHA and BHT shown below).
two,half dozen-Xylenol	3D
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Xylenol is a trivial proper name given to the six isomeric dimethylphenols.  The name is derived from xylene, which is the trivial proper name for the three isomeric dimethylbenzenes.  The construction shown above is 2,6-xylenol, or ii,half-dozen-dimethylphenol; the other isomers are shown below. The xylenols are found in a number of pesticides, and are also used in the industry of many other compounds.
iv-Chloro-3,5-dimethylphenol (Chloroxylenol)	3D
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4-Chloro-3,five-dimethylphenol, or chloroxylenol, is a nonirritating topical clarified used in a number of antibacterial soaps.
BHA (butylated hydroxy anisole)	3D
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Butylated hydroxy anisole (BHA), or 2-tert-butyl-4-methoxyphenol, is a commonly used antioxidant.  (Anisole itself is a benzene ring with a methoxy, OCH3, group.)  Together with the 3-tert-butyl isomer (not shown), this chemical compound is commonly added to foods, gasoline, oils, safety, and other products to react with and thereby neutralize the free radicals that would otherwise damage the products.
BHT (butylated hydroxy toluene)	3D
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Butylated hydroxy toluene (BHT), or 2,half dozen-di-tert-butyl-4-methylphenol, is some other common antioxidant, used to preclude the spoiling of some foods, as well every bit to preserve cosmetics, drugs, gasoline, oils, rubber, and other products.
ii,four,6-Trinitrophenol (Picric acid)	3D
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2,iv,half-dozen-Trinitrotoluene, or picric acid, is a yellowish, crystalline substance that is explosive when it is dry.  Information technology is fairly stable when wet, but the dry out form is extremely sensitive to stupor or friction.  It was extensively used in arms shells in the belatedly 1800's and early 1900'south, but was somewhen replaced by 2,4,6-trinitrotoluene (TNT, in which the OH in the construction above is replaced with a methyl group), which was more than stable and less prone to forming dangerous metal salts when stored in a vanquish casing. Picric acid was a component in the Halifax Explosion, which occurred when a French cargo ship, the Mont-Blanc, carrying nitrocellulose, picric acid, and TNT, collided with a Norwegian ship, the Imo, which was carrying relief supplies to Belgium, in the harbor of Halifax, Nova Scotia, Canada on December 6, 1917.  The Mont-Blanc exploded before long after the collision, leveling all of the structure within two square kilometers of the harbor, and causing a tidal wave in the harbor; approximately 2,000 people were killed and over 9,000 injured.  The explosion was the largest human being-made chemical explosion always recorded.
Catechol	3D
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Catechol, or 1,2-benzenediol, or 2-hydroxyphenol, contains ii OH groups ortho to each other on a benzene ring.  The catechol structure is establish in the urushiols, the peel irritants in toxicant ivy (encounter below), and is besides constitute in many of import neurotransmitters (run into page on neurotransmitters for examples).
Urushiols	3D
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The urushiols consists of a cathechol band to which is attached a long hydrocarbon concatenation, consisting of xv to 17 carbons, which may be saturated, unsaturated, or polyunsaturated.  These viscous oils cause skin rashes (urushiol-induced contact dermatitis), and are found in the plants of the genus Toxicodendron, such equally poison ivy (Toxicodendron radicans), poison oak (Toxicodendron diversilobum, Toxicodendron pubescens), and poisonous substance sumac (Toxicodendron vernix); they are also constitute in the shell of the cashew (Anacardium occidentale) and the skin of the fruit of the mango tree (Mangifera indica).	The 3D structure shown above is that of the first R group listed in the 2d structure.
Resorcinol	3D
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Resorcinol, or one,iii-benzenediol, or 3-hydroxyphenol, contains two OH groups meta to each other on a benzene band.  It if found in many resins; it is used as an clarified and disinfectant, in the treatment of psoriasis, eczema, and other skin weather, and is found in some shampoos as a treatment for dandruff.
4-Hexylresorcinol	3D
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4-Hexylresorcinol is used in some mouthwashes, throat lozenges, and some skin medications.
Hydroquinone	3D
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Hydroquinone, or 1,4-benzenediol, or iv-hydroxyphenol, contains 2 OH groups para to each other on a benzene ring.  Hydroquinone is easily oxidized by mild oxidizing agents to produce para-benzoquinone (which is oftentimes merely called quinone), which itself is easily reduced by mild reducing agents back to the hydroquinone class: This reversible redox reaction involving hydroquinone and quinone is exploited past nature in enzyme-catalyzed electron transport reactions in the grade of the ubiquonones (see entry beneath). Hydroquinone is also used in photograph developing solutions (in non-digital photography, of course), where information technology helps to reduce silvery halides to metal silver. Hydroquinone is besides function of the chemical defensive system employed by the bombardier beetle (family Carabidae).  Hydroquinone is mixed with hydrogen peroxide from a carve up reservoir in the beetle'southward body, which oxidizes the hydroquinone into quinone, generating enough oestrus to boil the solution, producing a hot, corrosive, defensive spray.	para-benzoquinone Download 3D
Ubiquinones	3D
	Download 3D The construction shown above is the ubiquinone grade with due north=half-dozen
The ubiquinones, likewise known equally the coenzymes Q, are quinone derivatives (see higher up) which have isoprene-derived hydrocarbon chains.  These moleculess are found in the mitrochondria of all living cells (hence the name: ubiquitous quinones), as well as in other organelles such equally the endoplasmic reticulum, peroxisomes, lysosomes, and vesicles; in humans the isoprene chain is 10 units long, and is known every bit Coenzyme Qx.  The ubiquinones acquit electrons through the electron transport chain in mitochondria, and aid the mitochondria to produce energy.  The ubiquinones besides act as antioxidants, protecting organelle and cell membranes from costless radicals.
1-Napthol	3D
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ane-Napthol consists of ii fused benzene rings (naphthalene) with a OH group attached to position ane.  There is one other structural isomer, not shown, in which the OH is attached to position ii.
Calixarenes	3D
4-tert-Butylcalix[4]arene	Download 3D
The calixarenes are macrocycles (large molecular rings) formed by the reaction of phenols with aldehydes.  These molecules form three-dimensional shapes that resemble a bowl or a loving cup, from which the proper noun "calixarene" is derived (Latin, calix, for "cup" or "beaker" + arene for the aromatic ring portion of the molecule).  The iv oxygen atoms pointing toward the center of the "cup" tin form complexes with Lewis acids, and calixarenes of various sizes can be synthesized that are capable of forming coordination complexes with a wide variety of metal ions, such as sodium (where it is used in probes to measure sodium levels in blood), lead, cadmium, mercury, cesium, potassium, calcium, lithium, and silver.
Anthocyanidins	3D
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The anthocyanidins are members of a class of compounds chosen the flavonoids (see page on Ketones); they are pigments found in a wide range of plants, and are normally either red, bluish, or purple, depending on the pH of their environs.  Because their colors change with pH, they are oft used in acrid-base of operations indicators.  The positively charged oxygen atom, known equally a benzopyrilium cation, is unremarkably associated with a chloride anion.  Almost anthocyanidins are combined with saccharide molecules to make glycosides called anthocyanins (Greek, "blue flower"). The anthocyanidins are antioxidants, protecting plants cells from damage caused past high-energy sunlight.  Their bright colors assistance the plants to attract insect pollinators, also every bit animals that eat the fruit of the plants and thereby distribute its seeds. The autumn colors of many copse are partly caused by the production of anthocyanidins as chlorophyll in the leaves breaks down; the carotenes in the leaves too contribute to the autumn colors. Some examples of the anthocyanidins are listed below:	The 3D structure shown in a higher place is that of pelargonidin:

	Ri	R2	Riii	R4	R5	Rhalf dozen	R7	Occurrence
Apigeninidin	H	OH	H	H	OH	H	OH	an anti-microbial antioxidant fount in the foliage sheath of genus Sorghum
Aurantinidin	H	OH	H	OH	OH	OH	OH	found in the flowers of the genus Impatiens (family Balsaminaceae)
Capensinidin	OCH3	OH	OCHiii	OH	OCH3	H	OH
Cyanidin	OH	OH	H	OH	OH	H	OH	found in a broad variety of berries, such as bilberries, blackberries, blueberries, cherries, cranberries, elderberries, hawthorn, loganberries, plums,  raspberries, and strawberries; likewise found in apple skins, cherry cabbage, and rhubarb
Delphinidin	OH	OH	OH	OH	OH	H	OH	causes the bluish color of violets (genus Viola) and delphiniums (genus Delphinium); also found in cranberries, Concord grapes, and the Cabernet Sauvignon grape
Europinidin	OCHiii	OH	OH	OH	OCHiii	H	OH
Hirsutidin	OCH3	OH	OCH3	OH	OH	H	OCH3
Luteolinidin	OH	OH	H	H	OH	H	OH	found in the fern Blechnum novae-zelandiae (family Blechnaceae)
Malvidin	OCH3	OH	OCH3	OH	OH	H	OH	found in the European grapevine (Vitis vinifera), and responsible for the color of ruby vino; also responsible for the blueish colour of some flowers of the genus Primula (family Primulaceae)
Pelargonidin	H	OH	H	OH	OH	H	OH	responsible for the blood-red colour of the geranium (genus Geranium) and pelargoniums (genus Pelargonium); likewise plant in raspberries and strawberries
Peonidin	OCHthree	OH	H	OH	OH	H	OH	found in the peony (genus Paeonia), roses, morn glories (family Convolvulaceae); also found in cherries, grapes, and cranberries
Petunidin	OH	OH	OCHiii	OH	OH	H	OH	found in the flowers of the genus Petunia (family Solanaceae)
Pulchellidin	OH	OH	OH	OH	OCH3	H	OH
Rosinidin	OCH3	OH	H	OH	OH	H	OCH3
Tricetinidin	OH	OH	OH	H	OH	H	OH

(1) Isaac Asimov, Isaac Asimov'south Biographical Encyclopedia of Science and Technology.  New York:  Avon Books, 1976, p. 388.

P. W. Atkins, Molecules, 2nd ed.  Cambridge: Cambridge University Press, 2003, p. 174-176.

Jin-Ming Kong, Lian-Sai Chia, Ngoh-Khang Goh, Tet-Fatt Chia, and R. Brouillard, "Analysis and biological activities of anthocyanins" (Phytochemistry, 2003, 64, 923)

Richard J. Lewis, Sr., Hawley'south Condensed Chemical Dictionary, 13th ed.  New York:  Van Nostrand Reinhold, 1997.

D. West. A. Sharp, The Penguin Dictionary of Chemical science, 2nd ed.  London:  Penguin Books, 1990.

Graham Solomons and Craig Fryhle, Organic Chemical science, 7th ed.  New York:  John Wiley & Sons, Inc., 2000, p. 1014-1017, 1030-1031.

Jeffrey B. Harborne and Christine A. Williams, "Anthocyanins and other flavonoids."  (Natural Products Reports, 1998, 15, 631-652).

Jeffrey B. Harborne and Christine A. Williams, "Anthocyanins and other flavonoids."  (Natural Products Reports, 2001, xviii, 310-333).

Christine A. Williams and Ren�e J. Grayer, "Anthocyanins and other flavonoids."  (Natural Products Reports, 2004, 21, 539-573).

Martha Windholz (ed.), The Merck Alphabetize, 10th ed. Rahway: Merck & Co., Inc., 1983.

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Source: https://www.angelo.edu/faculty/kboudrea/molecule_gallery/06_phenols/00_phenols.htm

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