Chrysoine resorcinol
{{Redirect|Gold yellow|the colour|golden yellow}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 421100892
| ImageFile = Chrysoine resorcinol.svg
| ImageSize = 240px
| ImageAlt = Skeletal formula of chrysoine resorcinol as a sodium salt
| ImageFile1 = Chrysoine resorcinol sodium 3D spacefill.png
| ImageSize1 = 240
| ImageAlt1 = Space-filling model of chrysoine resorcinol as a sodium salt
| IUPACName = Sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate
| OtherNames = Sodium p-(2,4-dihydroxyphenylazo)benzenesulfonate; Chrysoine; Resorcinol Yellow; Gold Yellow; Yellow T; Tropaeolin O; Tropaeolin R; C.I. Food Yellow 8; C.I. Acid Orange 6; C.I. 14270
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 21106427
| InChI = 1/C12H10N2O5S.Na/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19;/h1-7,15-16H,(H,17,18,19);/q;+1/p-1/b14-13+;
| InChIKey = COEZWFYORILMOM-WTMITFMSBV
| InChI1 = 1/C12H10N2O5S.C6H6O2.Na/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19;7-5-2-1-3-6(8)4-5;/h1-7,15-16H,(H,17,18,19);1-4,7-8H;/q;;+1/p-1/b14-13+;;
| InChIKey1 = DJYSHZPRWDNEOL-MNMGBGISBV
| SMILES1 = [Na+].Oc2cc(O)ccc2/N=N/c1ccc(cc1)S([O-])(=O)=O.Oc1cccc(O)c1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H10N2O5S.C6H6O2.Na/c15-9-3-6-11(12(16)7-9)14-13-8-1-4-10(5-2-8)20(17,18)19;7-5-2-1-3-6(8)4-5;/h1-7,15-16H,(H,17,18,19);1-4,7-8H;/q;;+1/p-1/b14-13+;;
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DJYSHZPRWDNEOL-QDBORUFSSA-M
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 547-57-9
| PubChem = 6093186
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = NF91VMI73L
| SMILES = [Na+].Oc2cc(O)ccc2/N=N/c1ccc(cc1)S([O-])(=O)=O
| EINECS = 208-924-8
}}
|Section2={{Chembox Properties
| C=12 | H=9 | N=2 | Na=1 | O=5 | S=1
| Appearance = Orange-yellow solid
| Density =
| MeltingPt =
| BoilingPt =
| Solubility = Partially soluble
}}
|Section3={{Chembox Hazards
| MainHazards =
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| FlashPt =
| AutoignitionPt =
}}
}}
Chrysoine resorcinol is a synthetic azo dye which was formerly used as a food additive.{{Citation needed|date=November 2010}} In Europe, it was banned as a food additive in 1977.{{Cite web|url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31976L0399:EN:HTML|title=EUR-Lex - Official Journal of the European Union}} In the US, it was banned in 1988.{{Cite web |title=Chrysoine Resorcinol Properties, Molecular Formula, Applications - WorldOfChemicals |url=https://www.worldofchemicals.com/chemicals/chemical-properties/chrysoine-resorcinol.html |access-date=2022-07-12 |website=www.worldofchemicals.com}}
Chrysoine resorcinol can be used as a pH indicator with a color change between pH 11 and pH 12.7.
In colorimetry, it has an absorption maximum of 387 nm.
{{left|{{pH_indicator_template | indicator_name=Chrysoine resorcinol | low_pH=11.0 | high_pH=12.7 | low_pH_color=yellow | high_pH_color=red |high_pH_text=white }}}}
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Preparation
Acid orange 6 can be synthesised via the azo coupling of sulfanilic acid and resorcinol,
Notes
{{Reflist}}
External links
- [http://www.inchem.org/documents/jecfa/jecmono/v12je12.htm Data at inchem.org]
- [https://fscimage.fishersci.com/msds/98969.htm MSDS at Fischer Scientific]
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