Resorcinol
1207055
225093953
2008-07-11T21:11:54Z
Pmcginty
2053514
/* Medical */
{{Chembox new
| Name = Resorcinol
| ImageFile = Resorcinol.svg
<!-- | ImageSize = 150px -->
| ImageName = Resorcinol
| ImageFile1 = Resorcinol-3d.png
<!-- | ImageSize1 = 150px -->
| IUPACName = Benzene-1,3-diol
| OtherNames = Resorcin<br />m-dihydroxybenzene; 1,3-benzenediol; 1,3-Dihydroxybenzene; 3-Hydroxyphenol
| Section1 = {{Chembox Identifiers
| SMILES = Oc1cc(O)ccc1
| CASNo = 108-46-3
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub>
| MolarMass = 110.1 g/mol
| Appearance = white solid
| Density = 1.28 g/cm<sup>3</sup>, solid
| Solubility = Very soluble (110 g/100 mL at 20 deg C)
| MeltingPt = 110 °C
| BoilingPt = 277 °C
| pKa =
}}
| Section3 = {{Chembox Structure
| Dipole =
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| EUClass = Harmful ('''Xn''')<br />Dangerous for<br />the environment ('''N''')
}}
}}
'''Resorcinol''' (or '''resorcin''') is a [[chemical compound]] from the dihydroxy [[phenol]]s. it is the 1,3-[[isomer]] of [[benzenediol]]. It is also known with a variety of other names, including: m-dihydroxybenzene, 1,3-benzenediol, 1,3-dihydroxybenzene, 3-hydroxyphenol, m-hydroquinone, m-benzenediol, and 3-hydroxycyclohexadien-1-one.
==Nomenclature==
Benzene-1,3-diol is the name recommended by the [[International Union of Pure and Applied Chemistry]] (IUPAC) in its ''1993 Recommendations for the Nomenclature of Organic Chemistry''.<ref>{{cite book | author=Panico, R.; & Powell, W. H. (Eds.) | title=A Guide to IUPAC Nomenclature of Organic Compounds 1993 | location=Oxford | publisher=Blackwell Science | year=1994 | id=ISBN 0-632-03488-2}}</ref>
==Production==
It is obtained on fusing many [[resin]]s ([[galbanum]], [[asafoetida]], etc.) with [[potassium hydroxide]], or by the [[distillation]] of [[Brazilwood]] extract. It may be prepared [[organic synthesis|synthetically]] by fusing [[3-Iodophenol|3-iodophenol]], [[phenol-3-sulfonic acid]] or [[benzene-1,3-disulfonic acid]] with [[potassium carbonate]]; by the action of [[nitrous acid]] on [[3-Aminophenol|3-aminophenol]]; or by the action of 10% [[hydrochloric acid]] on [[1,3-diaminobenzene]] <ref>{{cite journal|journal = Ber | first = J |last = Meyer | year = 1897 |pages = 2569 |volume = 30}}</ref>. Many ''ortho''- and ''para''-compounds of the [[aromatic]] series (for example, the bromophenols, benzene-''para''-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide.
==Properties==
Resorcinol crystallizes from [[benzene]] as colorless needles which are readily soluble in water, alcohol and ether, but insoluble in [[chloroform]] and [[carbon disulfide]]. It reduces [[Fehling's solution]], and [[Tollens' reagent|ammoniacal silver solutions]]. It does not form a precipitate with [[lead acetate]] solution, as the isomeric [[pyrocatechol]] does. [[Iron(III) chloride]] colors its aqueous solution a dark violet, and [[bromine]] water precipitates tribromoresorcin. These properties are what give it its use as a colouring agent for certain [[Chromatography]] experiments. [[Sodium amalgam]] reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated [[barium hydroxide]] solution gives γ-acetylbutyric acid (D. Vorlgnder); when fused with potassium hydroxide, resorcinol yields [[phloroglucin]], pyrocatechol and [[diresorcin]]. It [[condensation reaction|condenses]] with [[acid]]s or [[acid chloride]]s, in the presence of dehydrating agents, to oxyketones, e.g. with [[zinc chloride]] and glacial [[acetic acid]] at 145 °C it yields resacetophenone (HO)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>~CO.CH<sub>3</sub>(M. Nencki and N. Sieber, Jour. prak. Chem., 1881, 23, p. 147). With the [[anhydride]]s of dibasic acids it yields [[fluorescein]]s. When heated with [[calcium chloride]]—[[ammonia]] to 200 °C it yields meta-dioxydiphenylamine (A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811). With [[sodium nitrite]] it forms a water-soluble blue dye, which is turned red by acids, and is used as an [[indicator]], under the name of lacmoid (M. C. Traub and C. Hock, Ber., 1884, 17, p. 2615). It condenses readily with [[aldehyde]]s, yielding with [[formaldehyde]], on the addition of catalytic [[hydrochloric acid]], methylene diresorcin [(HO)C<sub>6</sub>H<sub>3</sub>(O)]<sub>2</sub>•CH<sub>2</sub>, whilst with [[chloral hydrate]], in the presence of [[Potassium hydrogensulfate|potassium bisulfate]], it yields the [[lactone]] of tetra-oxydiphenyl methane carboxylic acid (J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084). In alcoholic solution it condenses with [[sodium acetoacetate]] to form 13-methylumbelliferone, C~OH<sub>8</sub>O<sub>3</sub> (A. Michael, Jour. prak. Chem., 1888, 37, 470).
With concentrated [[nitric acid]], in the presence of cold concentrated [[sulfuric acid]], it yields trinitro-resorcin ([[styphnic acid]]), which forms yellow crystals, exploding violently on rapid heating.
==Applications==
===Medical===
Used externally it is an [[antiseptic]] and [[disinfectant]], and is used 5 to 10% in ointments in the treatment of chronic skin diseases such as [[psoriasis]] and [[eczema]] of a sub-acute character.{{Fact|date=October 2007}} It is present in over-the-counter topical [[acne]] treatments at 2% concentration, and in prescription treatments at higher concentrations.{{Fact|date=October 2007}} Weak, watery solutions of resorcinol (25 to 35 g/kg) are useful in allaying the itching in [[erythematous eczema]].{{Fact|date=October 2007}} A 2% solution used as a spray has been used with marked effect in [[hay fever]] and in [[whooping cough]].{{Fact|date=October 2007}} In the latter disease 0.6 mL of the 2% solution has been given internally. It can be included as an anti-[[dandruff]] agent in [[shampoo]] or in [[sunscreen]] cosmetics.{{Fact|date=October 2007}} It has also been employed in the treatment of [[gastric ulcer]]s in doses of 125 to 250 mg in pills, and is said to be [[analgesic]] and [[haemostatic]] in its action.{{Fact|date=October 2007}} In large doses it is a [[poison]] causing [[giddiness]], [[deafness]], [[salivation]], [[sweating]] and [[convulsions]]. It is also worked up in certain medicated soaps.{{Fact|date=October 2007}} Monoacetylresorcinol, C<sub>6</sub>H<sub>4</sub>(OH)(O-COCH<sub>3</sub>), is used under the name of '''euresol'''.{{Fact|date=October 2007}} Resorcinol is one of the main active ingredients in products like [[Resinol]] and [[Vagisil]].
===Chemical===
Resorcinol is also used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of diazo dyes and plasticizers and as a [[UV]] absorber in resins.
An emerging use of resorcinol is as a template molecule in [[supramolecular chemistry]]. The -OH groups on resorcinol form [[hydrogen bond]]s to target molecules holding them in the proper orientation for a reaction. Many such reactions are able to be carried out in the [[Phase (matter)|solid state]] thereby reducing or eliminating the use of solvents that may be harmful to the environment. (see [[Green chemistry]])
Resorcinol is an analytical reagent for the qualitative determinaion of ketoses ([[Seliwanoff's test]]).
Resorcinol is the starting material for [[resorcinarene]] molecules.
==Related compounds==
[[Resazurin]], C<sub>12</sub>H<sub>7</sub>NO<sub>4</sub>, obtained by the action of nitrous acid on resorcinol <ref>{{cite journal | first = P | last = Weselsky | coauthors = Benedikt, R | journal = Monats. | year = 1880 | volume = f | pages = 889}}</ref>, forms small dark red crystals possessing a greenish metallic glance. When dissolved in concentrated sulfuric acid and warmed to 210 °C, the solution on pouring into water yields a precipitate of resorufin, C<sub>12</sub>H<sub>7</sub>NO<sub>3</sub>, an oxyphenoxazone, which is insoluble in water, but is readily soluble in hot concentrated hydrochloric acid, and in solutions of caustic alkalis. The alkaline solutions are of a rose-red color and show a cinnabar-red fluorescence. A tetrabromresorufin is used as a dye-stuff under the name of Fluorescent Resorcin Blue.
Thioresorcinol is obtained by the action of zinc and hydrochloric acid on the chloride of benzene meta-disulfonic acid. It melts at 27 °C and boils at 243 °C. Resorcinol disulfonic acid (HO)<sub>2</sub>C<sub>6</sub>H<sub>2</sub>(HSO3)<sub>2</sub>, is a deliquescent mass obtained by the action of sulfuric acid on resorcin <ref>{{cite journal | first = H | last = Fischer | journal = Monats. | year = 1881 | volume = 2 | pages = 321}}</ref>. It is easily soluble in water and decomposes when heated to 100 °C.
==References==
{{Unreferenced|date=September 2007}}
{{reflist}}
==External links==
*[http://www.ilo.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc10/icsc1033.htm International Chemical Safety Card 1033]
*[http://www.cdc.gov/niosh/npg/npgd0543.html NIOSH Pocket Guide to Chemical Hazards]
*[http://www-cie.iarc.fr/htdocs/monographs/vol71/046-resorcinol.html IARC Monograph: "Resorcinol"]
*{{ecb}}
*[http://www.acdlabs.com/iupac/nomenclature/ IUPAC Nomenclature of Organic Chemistry] (online version of the "''Blue Book''")
{{1911}}
[[Category:Benzenediols]]
[[Category:Phenols]]
[[Category:IARC Group 3 carcinogens]]
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