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aurin

Structure via PubChem · Public domain (PubChem)

EntityQ423995· pop 18· linked from 8 articles

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. 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.

Chemical data

Formula
C19H14O3
Molecular weight
290.3 g/mol
IUPAC name
4-[bis(4-hydroxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
SMILES
C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O
InChIKey
FYEHYMARPSSOBO-UHFFFAOYSA-N
XLogP
3.9
Polar surface area
57.5 Ų
H-bond donors
2
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Has part
carbon
Mass
290.094
Show 4 more facts
chemical formula
C₁₉H₁₄O₃
canonical SMILES
C1=CC(=O)C=CC1=C(C2=CC=C(C=C2)O)C3=CC=C(C=C3)O
Commons category
Aurin (chemical)
Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

4 sections
Contents
  • Synthesis
  • Safety
  • References
  • External links

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. 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). 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. (Gradually, chemists realized that commercial aurin was not a pure compound, but was actually a mixture of similar compounds.)

Excerpted from Wikipedia’s “aurin” article, available under the CC BY-SA 4.0 licence.

Gallery (3)