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Revision as of 22:05, 11 October 2011 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added CSID, (Std)InChI & (Std)InChIKey← Previous edit Latest revision as of 09:58, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits added Category:4-Hydroxyphenyl compounds using HotCat 
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⚫ {{for|the French commune|Aurin, Haute-Garonne}}
{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 414758567 | verifiedrevid = 455111505
| ImageFile = Aurin.svg | ImageFile = Aurin.svg
| ImageSize = 180px | ImageSize = 180px
Line 8: Line 9:
| ImageSize1 = 180px | ImageSize1 = 180px
| ImageName1 = Ball-and-stick model | ImageName1 = Ball-and-stick model
| IUPACName = 4--<br>-2,5-cyclohexadien-1-one | PIN = 4-cyclohexa-2,5-dien-1-one
| OtherNames = Aurin, corallin, p-rosolic acid, C.I. 43800 | OtherNames = Aurin, corallin, p-rosolic acid, C.I. 43800
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 603-45-2
| EINECS = 210-041-8 | CASNo = 603-45-2
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 5100
| UNII = 85N4AK3JAU
⚫ | ChEMBL_Ref = {{ebicite|changed|EBI}}
| EINECS = 210-041-8
⚫ | PubChem = 5100
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 210868 | ChEMBL = 210868
| SMILES = C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O | SMILES = C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O
| Beilstein = 2055205 | Beilstein = 2055205
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4921 | ChemSpiderID = 4921
| 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 | 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
| InChIKey = FYEHYMARPSSOBO-UHFFFAOYAG | InChIKey = FYEHYMARPSSOBO-UHFFFAOYAG
⚫ | StdInChI = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = FYEHYMARPSSOBO-UHFFFAOYSA-N
⚫ | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = FYEHYMARPSSOBO-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=19 | H=14 | O=3
| Formula = C<sub>19</sub>H<sub>14</sub>O<sub>3</sub>
⚫ | Appearance = ''see text''
| MolarMass = 290.313 g/mol
⚫ | Density = 1.283 g/cm<sup>3</sup>
⚫ | Appearance =
| MeltingPtC = 308
⚫ | Density = 1.283 g cm<sup>-3</sup>
| MeltingPt_notes = (decomposes)
| MeltingPt = 308 °C (decomp.)
| BoilingPt = | BoilingPt =
| Solubility = insoluble | Solubility = Insoluble
| LambdaMax = 482 nm<ref name="sigma">{{Sigma-Aldrich|id=861324|name=p-Rosolic acid|accessdate=2014-05-06}}</ref>
| MagSus = -161.4·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}<ref name="sigma" />
| MainHazards =
| NFPA-H = 1 | GHSSignalWord = Danger
| HPhrases = {{H-phrases|315|319|335}}<ref name="sigma" />
⚫ | NFPA-F = 1
| PPhrases = {{P-phrases|261|305+351+338}}<ref name="sigma" />
| NFPA-R = 0
| NFPA-O = | MainHazards =
⚫ | NFPA-H = 1
| RPhrases = {{R36}} {{R37}} {{R38}}
| SPhrases = | NFPA-F = 1
| FlashPt = 308 °C | NFPA-R = 0
| Autoignition = | NFPA-S =
| FlashPtC =
| AutoignitionPtC =
}} }}
}} }}
⚫ :''For the French commune, see ].
:''For the Aragonese village, see ].


'''Aurin''' ('''C.I. 43800'''), sometimes named '''rosolic acid''' or '''corallin''' is an ], forming yellowish or deep-red crystals with greenish metallic luster. It is practically insoluble in water, freely soluble in ]. It is soluble in strong acids to form yellow solution, or in aqueous ]s to form carmine red solutions. Due to this behaviour it can be used as ] with pH transition range 5.0 - 6.8. It used as intermediate in manufacturing of ]s. '''Aurin''' ('''C.I. 43800'''), sometimes named '''rosolic acid''' or '''corallin''' is an ], forming ]ish or deep-red crystals with ]ish metallic luster. It is practically insoluble in water, freely soluble in ]. It is soluble in strong acids to form yellow solution, or in aqueous ]s to form ] red solutions. {{pH_indicator|indicator_name=Aurin|low_pH=5.0|high_pH=6.8|low_pH_color=yellow|high_pH_color=#960018|high_pH_text=white}} Due to this behaviour it can be used as ] with pH transition range 5.0 - 6.8. It is used as an intermediate in manufacturing of ]s.


==Synthesis== ==Synthesis==
Aurin was first prepared in 1834 by the German chemist ], who obtained it by distilling coal tar. He named it ''Rosölsäure'' or ''Rosaölsäure'' (red oil acid).<ref>{{cite journal|last1=Runge|first1=F. F.|title=Ueber einige Produkte der Steinkohlendestillation|journal=Annalen der Physik und Chemie|date=1834|volume=31|issue=5 |pages=65–78|doi=10.1002/andp.18341070502 |bibcode=1834AnP...107...65R |url=https://babel.hathitrust.org/cgi/pt?id=nyp.33433062753029;view=1up;seq=87|trans-title=On some products of coal tar distillation|language=German}} ; see p. 70.</ref><ref>In 1859, the German-English chemist ] (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. {{cite journal|last1=Müller|first1=Hugo|title=Note on rosolic acid|journal=Quarterly Journal of the Chemical Society|date=1859|volume=11|issue=1|pages=1–5|doi=10.1039/QJ8591100001|url=https://babel.hathitrust.org/cgi/pt?id=njp.32101046329080;view=1up;seq=11}}</ref> In 1861, the German chemists ] and ] presented the synthesis of aurin by heating oxalic acid and ] (which contains phenol) in the presence of concentrated sulfuric acid.<ref>{{cite journal|last1=Kolbe|first1=H.|last2=Schmitt|first2=R.|title=Rother Farbstoff aus dem Kreosot|journal=Annalen der Chemie|date=1861|volume=119|pages=169–172|url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457957;view=1up;seq=181|trans-title=Red dye from creosote|language=German}}</ref> (Gradually, chemists realized that commercial aurin was not a pure compound, but was actually a mixture of similar compounds.<ref>See the papers of the English chemist Richard S. Dale and the German-English chemist ] and of the German chemist ] (1847–1920).
* {{cite journal|last1=Dale|first1=R.S.|last2=Schorlemmer|first2=C.|title=On aurin|journal=Journal of the Chemical Society|date=1871|volume=24|pages=466–467|doi=10.1039/JS8712400466|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx1dr8;view=1up;seq=504}}
* {{cite journal|last1=Dale|first1=R.S.|last2=Schorlemmer|first2=C.|title=On aurin|journal=Journal of the Chemical Society|date=1872|volume=25|pages=74–75|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx1dr9;view=1up;seq=82}}
* {{cite journal|last1=Dale|first1=R.S.|last2=Schorlemmer|first2=C.|title=On aurin|journal=Journal of the Chemical Society|date=1873|volume=26|pages=434–444|doi=10.1039/JS8732600434|url=https://books.google.com/books?id=h-41AQAAMAAJ&pg=PA434}}
* {{cite journal|last1=Dale|first1=R.S.|last2=Schorlemmer|first2=C.|title=On aurin, part II|journal=Journal of the Chemical Society|date=1879|volume=35|pages=148–159|doi=10.1039/CT8793500148|url=https://books.google.com/books?id=WSxEAQAAMAAJ&pg=PA148}}
* {{cite journal|last1=Fresenius|first1=H.|title=Ueber Rosolsäure|journal=Journal für praktische Chemie|date=1871|volume=3|pages=477–480|url=https://babel.hathitrust.org/cgi/pt?id=njp.32101076786365;view=1up;seq=491|series=2nd series|doi=10.1002/prac.18710030149|trans-title=On rosolic acid|language=German}}
* A review of findings about aurin up to 1872 appeared in: {{cite journal|last1=Fresenius|first1=H.|title=Ueber das Corallin|journal=Journal für praktische Chemie|date=1872|volume=5|issue=4|pages=184–191|url=https://babel.hathitrust.org/cgi/pt?id=pst.000067439980;view=1up;seq=196|series=2nd series|doi=10.1002/prac.18720050117|trans-title=On corallin|language=German}}
* {{cite journal|last1=Fresenius|first1=H.|title=Corallin|journal=Journal of the Chemical Society|date=1872|volume=25|pages=705–706|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx1dr9;view=1up;seq=749}}</ref><ref>Thorpe, Thomas Edward, ed., ''A Dictionary of Applied Chemistry'', 2nd ed. (London, England: Longmans, Green, and Co., 1913), vol. 5, "Triphenylmethane colouring matters," 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."</ref>)


Aurin is formed by heating of ] and ] in concentrated sulfuric acid. Aurin is formed by heating of ] and ] 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 ] (EDC) properties.<ref>{{cite journal | vauthors=((Blair, R. M.)) | journal=Toxicological Sciences | title=The Estrogen Receptor Relative Binding Affinities of 188 Natural and Xenochemicals: Structural Diversity of Ligands | volume=54 | issue=1 | pages=138–153 | date=1 March 2000 | issn=1096-0929 | doi=10.1093/toxsci/54.1.138| pmid=10746941 | doi-access=free }}</ref>{{rp|149}}


==References== ==References==
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==External links== ==External links==
* *
* *
*{{Cite NIE|wstitle=Aurin|short=x}}


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