Aurin

Last updated
Aurin
Aurin.svg
Aurin-3D-balls.png
Names
Preferred IUPAC name
4-[Bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
Other names
Aurin, corallin, p-rosolic acid, C.I. 43800
Identifiers
3D model (JSmol)
2055205
ChEMBL
ChemSpider
ECHA InfoCard 100.009.129 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-041-8
PubChem CID
UNII
  • InChI=1S/C19H14O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20-21H Yes check.svgY
    Key: FYEHYMARPSSOBO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C19H14O3/c20-16-7-1-13(2-8-16)19(14-3-9-17(21)10-4-14)15-5-11-18(22)12-6-15/h1-12,20-21H
    Key: FYEHYMARPSSOBO-UHFFFAOYAG
  • C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O
Properties
C19H14O3
Molar mass 290.318 g·mol−1
Appearancesee text
Density 1.283 g/cm3
Melting point 308 °C (586 °F; 581 K) (decomposes)
Insoluble
UV-vismax)482 nm [1]
-161.4·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg [1]
Danger
H315, H319, H335 [1]
P261, P305+P351+P338 [1]
NFPA 704 (fire diamond)
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Aurin(pH indicator)
below pH 5.0above pH 6.8
5.06.8

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.

Aurinsynthese.svg

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] :149

Related Research Articles

<span class="mw-page-title-main">Hermann Kolbe</span> German chemist (1818–1884)

Adolph Wilhelm Hermann Kolbe was a major contributor to the birth of modern organic chemistry. He was a professor at Marburg and Leipzig. Kolbe was the first to apply the term synthesis in a chemical context, and contributed to the philosophical demise of vitalism through synthesis of the organic substance acetic acid from carbon disulfide, and also contributed to the development of structural theory. This was done via modifications to the idea of "radicals" and accurate prediction of the existence of secondary and tertiary alcohols, and to the emerging array of organic reactions through his Kolbe electrolysis of carboxylate salts, the Kolbe-Schmitt reaction in the preparation of aspirin and the Kolbe nitrile synthesis. After studies with Wöhler and Bunsen, Kolbe was involved with the early internationalization of chemistry through work in London. He was elected to the Royal Swedish Academy of Sciences, and won the Royal Society of London's Davy Medal in the year of his death. Despite these accomplishments and his training important members of the next generation of chemists, Kolbe is best remembered for editing the Journal für Praktische Chemie for more than a decade, in which his vituperative essays on Kekulé's structure of benzene, van't Hoff's theory on the origin of chirality and Baeyer's reforms of nomenclature were personally critical and linguistically violent. Kolbe died of a heart attack in Leipzig at age 66, six years after the death of his wife, Charlotte. He was survived by four children.

<span class="mw-page-title-main">Phenols</span> Chemical compounds in which hydroxyl group is attached directly to an aromatic ring

In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (−OH) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, C
6
H
5
OH
. Phenolic compounds are classified as simple phenols or polyphenols based on the number of phenol units in the molecule.

<span class="mw-page-title-main">Phenol</span> Organic compound (C6H5OH)

Phenol is an aromatic organic compound with the molecular formula C6H5OH. It is a white crystalline solid that is volatile. The molecule consists of a phenyl group bonded to a hydroxy group. Mildly acidic, it requires careful handling because it can cause chemical burns.

<span class="mw-page-title-main">Aniline</span> Organic compound (C₆H₅NH₂); simplest aromatic amine

Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.

<span class="mw-page-title-main">Friedlieb Ferdinand Runge</span> German analytical chemist (1794 – 1867)

Friedlieb Ferdinand Runge was a German analytical chemist. Runge identified the mydriatic effects of belladonna extract, identified caffeine, and discovered the first coal tar dye.

<span class="mw-page-title-main">Gerardus Johannes Mulder</span>

Gerardus Johannes Mulder or Gerrit Jan Mulder was a Dutch organic and analytical chemist.

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

Resorcinol (or resorcin) is an organic compound with the formula C6H4(OH)2. It is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.

<span class="mw-page-title-main">Ferdinand Reich</span>

Ferdinand Reich was a German chemist who co-discovered indium in 1863 with Hieronymous Theodor Richter.

The Kolbe–Schmitt reaction or Kolbe process is a carboxylation chemical reaction that proceeds by treating phenol with sodium hydroxide to form sodium phenoxide, then heating sodium phenoxide with carbon dioxide under pressure, then treating the product with sulfuric acid. The final product is an aromatic hydroxy acid which is also known as salicylic acid.

Pelopium was the proposed name for a new element found by the chemist Heinrich Rose in 1845. The name derived from the Greek king and later god Pelops, son of Tantalus. During the analysis of the mineral tantalite he concluded that it does contain an element similar to niobium and tantalum. The similar reactivity of niobium and tantalum complicated preparation of pure samples and therefore several new elements were proposed, which were later found to be mixtures of niobium and tantalum.

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

Biuret is a chemical compound with the chemical formula HN(CONH2)2. It is a white solid that is soluble in hot water. A variety of organic derivatives are known. The term "biuret" also describes a family of organic compounds with the chemical formula R1R2N−C(=O)−N(R3)−C(=O)−NR4R5, where R1, R2, R3, R4 and R5 are hydrogen, organyl or other groups. Also known as carbamylurea, it results from the condensation of two equivalents of urea. As such, it is an undesirable impurity in urea-based fertilizers. As biuret is toxic to plants, its percentage in fertilizers must be kept low.

<span class="mw-page-title-main">Wilhelm Rudolph Fittig</span> German chemist (1835–1910)

Wilhelm Rudolph Fittig was a German chemist. He discovered the pinacol coupling reaction, mesitylene, diacetyl and biphenyl. Fittig studied the action of sodium on ketones and hydrocarbons. He discovered the Fittig reaction or Wurtz–Fittig reaction for the synthesis of alkylbenzenes, he proposed a diketone structure for benzoquinone and isolated phenanthrene from coal tar. He discovered and synthesized the first lactones and investigated structures of piperine naphthalene and fluorene.

<span class="mw-page-title-main">Zincke reaction</span>

The Zincke reaction is an organic reaction, named after Theodor Zincke, in which a pyridine is transformed into a pyridinium salt by reaction with 2,4-dinitro-chlorobenzene and a primary amine.

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

Phenyl salicylate, or salol, is the organic compound with the formula C6H5O2C6H4OH. It is a white solid. It is occasionally used in sunscreens and as an antiseptic.

<span class="mw-page-title-main">Johann Gottlieb</span> Austrian chemist (1815–1875)


Johann Gottlieb was an Austrian chemist who first synthesized Propionic acid. He is also known for describing and naming Paramylon.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound consisting of a 6-sided ring

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

Ilmenium was the proposed name for a new element found by the chemist R. Hermann in 1847. During the analysis of the mineral samarskite, he concluded that it does contain an element similar to niobium and tantalum. The similar reactivity of niobium and tantalum complicated preparation of pure samples of the metals and therefore several new elements were proposed, which were later found to be mixtures of niobium and tantalum.

Dianium was the proposed name for a new element found by the mineralogist and poet Wolfgang Franz von Kobell in 1860. The name derived from the Roman goddess Diana. During the analysis of the mineral tantalite and niobite he concluded that it does contain an element similar to niobium and tantalum. The symbol was Di.

<span class="mw-page-title-main">2,3-Dichloro-5,6-dicyano-1,4-benzoquinone</span> Chemical compound

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C6Cl2(CN)2O2. This oxidant is useful for the dehydrogenation of alcohols, phenols, and steroid ketones. DDQ decomposes in water, but is stable in aqueous mineral acid.

Radical theory is an obsolete scientific theory in chemistry describing the structure of organic compounds. The theory was pioneered by Justus von Liebig, Friedrich Wöhler and Auguste Laurent around 1830 and is not related to the modern understanding of free radicals. In this theory, organic compounds were thought to exist as combinations of radicals that could be exchanged in chemical reactions just as chemical elements could be interchanged in inorganic compounds.

References

  1. 1 2 3 4 Sigma-Aldrich Co., p-Rosolic acid. Retrieved on 2014-05-06.
  2. Runge, F. F. (1834). "Ueber einige Produkte der Steinkohlendestillation" [On some products of coal tar distillation]. Annalen der Physik und Chemie (in German). 31: 65–78. ; see p. 70.
  3. 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. Müller, Hugo (1859). "Note on rosolic acid". Quarterly Journal of the Chemical Society. 11 (1): 1–5. doi:10.1039/QJ8591100001.
  4. Kolbe, H.; Schmitt, R. (1861). "Rother Farbstoff aus dem Kreosot" [Red dye from creosote]. Annalen der Chemie (in German). 119: 169–172.
  5. 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).
  6. 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."
  7. Blair, R. M. (1 March 2000). "The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of Ligands". Toxicological Sciences. 54 (1): 138–153. doi: 10.1093/toxsci/54.1.138 . ISSN   1096-0929. PMID   10746941.