Orcinol
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| Names | |
|---|---|
| IUPAC name
5-Methylbenzene-1,3-diol
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| Other names
5-Methylresorcinol
3,5-Toluenediol Orcin 5-Methyl-1,3-benzenediol 3,5-Dihydroxytoluene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.259 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C7H8O2 | |
| Molar mass | 124.13 g/mol (anhydr.) |
| Appearance | Crystalline |
| Melting point | 110.0–110.5 °C – 107 °C (anhydr.) |
| Boiling point | 290 °C (289.5 °C) |
| Miscible | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Orcinol is a natural phenolic organic compound that occurs in many species of lichens[2] including Roccella tinctoria and Lecanora. Orcinol has been detected in the "toxic glue" of the ant species Camponotus saundersi.
Chemistry
It can be formed by fusing extract of aloes with potash.
It is used in the production of the dye orcein and as a reagent in some chemical tests for pentoses, such as Bial's Test. It may be synthesized from toluene; more interesting is its production when acetone dicarboxylic ester is condensed with the aid of sodium. It crystallizes in colorless prisms with one molecule of water, which redden on exposure to air. Ferric chloride gives a bluish-violet coloration with the aqueous solution. Unlike resorcinol it does not give a fluorescein with phthalic anhydride. Oxidation of the ammoniacal solution gives orcein, C28H24N2O7, the chief constituent of the natural dye archil. Homo-pyrocatechin is an isomer (CH1: OH: OH= 1 3 :4), found as its methyl ether (creosol) in beech-wood tar.
Orcinol
See also
References
- ^ Merck Index, 11th Edition, 6819.
- ^ Robiquet: „Essai analytique des lichens de l’orseille“, Annales de chimie et de physique, 1829, 42, p. 236–257.
- This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.
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