Chrysoine resorcinol

(Redirected from Acid Orange 6)

Chrysoine resorcinol is a synthetic azo dye which was formerly used as a food additive.[citation needed] In Europe, it was banned as a food additive in 1977.[1] In the US, it was banned in 1988.[2]

Chrysoine resorcinol
Skeletal formula of chrysoine resorcinol as a sodium salt
Space-filling model of chrysoine resorcinol as a sodium salt
Names
IUPAC name
Sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate
Other names
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
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.114 Edit this at Wikidata
EC Number
  • 208-924-8
UNII
  • InChI=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+;; checkY
    Key: DJYSHZPRWDNEOL-QDBORUFSSA-M checkY
  • 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+;
    Key: COEZWFYORILMOM-WTMITFMSBV
  • InChI=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+;;
    Key: DJYSHZPRWDNEOL-MNMGBGISBV
  • [Na+].Oc2cc(O)ccc2/N=N/c1ccc(cc1)S([O-])(=O)=O
  • [Na+].Oc2cc(O)ccc2/N=N/c1ccc(cc1)S([O-])(=O)=O.Oc1cccc(O)c1
Properties
C12H9N2NaO5S
Molar mass 316.26 g·mol−1
Appearance Orange-yellow solid
Partially soluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

Chrysoine resorcinol (pH indicator)
below pH 11.0 above pH 12.7
11.0 12.7

Preparation

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Acid orange 6 can be synthesised via the azo coupling of sulfanilic acid and resorcinol,

Notes

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  1. ^ "EUR-Lex - Official Journal of the European Union".
  2. ^ "Chrysoine Resorcinol Properties, Molecular Formula, Applications - WorldOfChemicals". www.worldofchemicals.com. Retrieved 2022-07-12.
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