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Orcein

Orcein

Class: Natural
Ionisation: Acid

Chemical structure of Orcein

Common Name: Orcein
Suggested Name: Orcein
Other Names:

C.I. Number: None (1st ed. 1242)
C.I. Name: Natural red 28
Color: Reddish brown
Solubility Aqueous: Poor
Solubility Ethanol: Poor
Absorption Maximum: 579 (Aldrich)
Empirical Formula:
Formula Weight:

Description

Orcein was originally obtained from lichens, but is now made from orcinol by hydrogen peroxide oxidation with ammonia present. It is a standard dye to use for the demonstration of elastic fibres, when it is applied in an acid, alcoholic solution. This same solution has also been shown to stain the rough endoplasmic reticulum of hepatitis B infected liver cells (ground glass cells).

Orcein is a variable mixture of several compounds. These compounds differ at the points marked R1, R2 and R3 in the structural formula. The chart below gives the commonest eight of these compounds, with the groups at each of the three points. The % column is the approximate percentage of each compound in synthetic orcein.

CompoundR1R2R3%
α-Aminoorcein
Chemical structure of α-Aminoorcein
HONH210
α-Hydroxyorcein
Chemical structure of α-Hydroxyorcein
HOOH10
β-Aminoorcein
Chemical structure of β-Aminoorcein
OrcinolONH26
γ-Aminoorcein
Chemical structure of γ-Aminoorcein
OrcinolONH212
β-Hydroxyorcein
Chemical structure of β-Hydroxyorcein
OrcinolOOH15
γ-Hydroxyorcein
Chemical structure of γ-Hydroxyorcein
OrcinolOOH10
β-Aminoorceimine
Chemical structure of β-Aminoorceimine
OrcinolNHNH21-2
γ-Aminoorceimine
Chemical structure of γ-Aminoorceimine
OrcinolNHNH21-2

References

  1. R. D. Lillie.
    Conn’s Biological Stains
    Williams & Wilkins, Baltimore, MD., U.S.A.
  2. Aldrich chemical catalogue, 1992
    Aldrich Chemical Company, Milwaukee, WI, USA.
  3. Susan Budavari, Editor,
    The Merck Index, Ed. 12
    Merck & Co., Inc., Whitehouse Station, NJ, USA