Haematoxylin

Haematoxylin
Names
Preferred IUPAC name
(6aS,11bR)-7,11b-Dihydroindolo[2,1-c] [1]benzopyran-3,4,6a,9,10(6H)-pentol
Other names
Hematoxylin; Natural Black 1; Hematoxyline; Hydroxybrazilin; Hydroxybrasilin; C.I. 75290
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.490
MeSH Hematoxylin
PubChem CID
UNII
  • InChI=1S/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13?,16-/m0/s1 Y
    Key: WZUVPPKBWHMQCE-VYIIXAMBSA-N Y
  • InChI=1/C16H14O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,13,17-21H,5-6H2/t13?,16-/m0/s1
    Key: WZUVPPKBWHMQCE-VYIIXAMBBJ
SMILES
  • Oc2cc3C[C@]4(O)COc1c(O)c(O)ccc1C4c3cc2O
Properties
C16H14O6
Molar mass 302.282 g·mol−1
Melting point 100-120 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Haematoxylin or hematoxylin (/ˌhməˈtɒksɪlɪn/), also called natural black 1 or C.I. 75290, is a compound extracted from heartwood of the logwood tree (Haematoxylum campechianum) with a chemical formula of C
16
H
14
O
6
. This naturally derived dye has been used as a histologic stain, as an ink and as a dye in the textile and leather industry. As a dye, haematoxylin has been called palo de Campeche, logwood extract, bluewood and blackwood. In histology, haematoxylin staining is commonly followed by counterstaining with eosin. When paired, this staining procedure is known as H&E staining and is one of the most commonly used combinations in histology. In addition to its use in the H&E stain, haematoxylin is also a component of the Papanicolaou stain (or Pap stain) which is widely used in the study of cytology specimens.

Although the stain is commonly called haematoxylin, the active colourant is the oxidized form haematein, which forms strongly coloured complexes with certain metal ions (commonly Fe(III) and Al(III) salts). In its pure form, haematoxylin is a colourless and crystalline solid, although commercial samples are typically light to dark brown based on the level of impurities present.

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