Chrysoine resorcinol

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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.114
EC Number
  • 208-924-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • [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
Chemical formula
 C12H9N2NaO5S
Molar mass 316.26 g·mol−1
Appearance Orange-yellow solid
Solubility in water
 Partially soluble
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
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 ?)
Infobox references

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

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

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

Notes

  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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