Aurin
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| Template:Longitem | 2055205 |
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| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | see text |
| Density | 1.283 g/cm3 |
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| UV-vis (λmax) | 482 nm[1] |
| Template:Longitem | −161.4·10−6 cm3/mol |
| NFPA 704 (fire diamond) | Template:NFPA 704 diamond |
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Aurin (C.I. 43800), sometimes named rosolic acid or corallin is an organic compound, forming yellowish or deep-red crystals with greenish metallic luster. It is practically insoluble in water, freely soluble in alcohol. It is soluble in strong acids to form yellow solution, or in aqueous alkalis to form carmine red solutions.
| Aurin (pH indicator) | ||
| below pH 5.0 | above pH 6.8 | |
| 5.0 | ⇌ | 6.8 |
Due to this behaviour it can be used as pH indicator with pH transition range 5.0 - 6.8. It is used as an intermediate in manufacturing of dyes.
Synthesis
Aurin was first prepared in 1834 by the German chemist Friedlieb Ferdinand Runge, who obtained it by distilling coal tar. He named it Rosölsäure or Rosaölsäure (red oil acid).[2][3] In 1861, the German chemists Hermann Kolbe and Rudolf Schmitt presented the synthesis of aurin by heating oxalic acid and creosote (which contains phenol) in the presence of concentrated sulfuric acid.[4] (Gradually, chemists realized that commercial aurin was not a pure compound, but was actually a mixture of similar compounds.[5][6])
Aurin is formed by heating of phenol and oxalic acid in concentrated sulfuric acid.
Safety
Aurin may cause eye, skin, and respiratory tract irritation. Ingestion and inhalation should be avoided.
Aurin was reported to have endocrine disruptor chemical (EDC) properties.[7]Template:Rp
References
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- ↑ a b c d Sigma-Aldrich Co., p-Rosolic acid. Retrieved on 2014-05-06.
- ↑ Script error: No such module "Citation/CS1". ; see p. 70.
- ↑ In 1859, the German-English chemist Hugo Müller (de) (1833–1915) found that rosolic acid could be produced simply by mixing phenol and calcium carbonate and then exposing the mixture to air for a prolonged time. Script error: No such module "Citation/CS1".
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- ↑ See the papers of the English chemist Richard S. Dale and the German-English chemist Carl Schorlemmer and of the German chemist Heinrich Fresenius (de) (1847–1920).
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- A review of findings about aurin up to 1872 appeared in: Script error: No such module "Citation/CS1".
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- ↑ Thorpe, Thomas Edward, ed., A Dictionary of Applied Chemistry, 2nd ed. (London, England: Longmans, Green, and Co., 1913), vol. 5, "Triphenylmethane colouring matters," p. 551. From p. 551: "The researches of Dale and Schorlemmer, Zulkowski, and others have shown that common aurin consists of a mixture of a number of substances, which, in a pure state, are well crystallised."
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