Haematoxylin

Haematoxylin
Haematoxylin powder
Skeletal formula of haematoxylin
Ball-and-stick model of the haematoxylin molecule
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 Edit this at Wikidata
MeSH Hematoxylin
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 checkY
    Key: WZUVPPKBWHMQCE-VYIIXAMBSA-N checkY
  • 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
  • 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 checkY☒N ?)

Haematoxylin or hematoxylin (/ˌhiːməˈtɒksɪlɪn/), also called natural black 1 or C.I. 75290, is a compound extracted from heartwood of the logwood tree (Haematoxylum campechianum)[1][2] with a chemical formula of C
16H
14O
6. This naturally derived dye has been used as a histologic stain, as an ink[3][4][5][6] and as a dye in the textile and leather industry.[7][8] As a dye, haematoxylin has been called palo de Campeche,[8] logwood extract,[7] bluewood[9] and blackwood.[9] In histology, haematoxylin staining is commonly followed by counterstaining with eosin.[1][10][11] When paired, this staining procedure is known as H&E staining and is one of the most commonly used combinations in histology.[1][7][12][13][14] 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.[1][14]

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).[1][7][8][15][16] In its pure form, haematoxylin is a colourless and crystalline solid,[7][17] although commercial samples are typically light to dark brown based on the level of impurities present.[2][18]

  1. ^ a b c d e Cite error: The named reference Bancroft and Stevens, 1982 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference Lillie, 1977 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Mitchell, 1908 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Barrow, 1948 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Centeno 2016 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Neevel, 2003 was invoked but never defined (see the help page).
  7. ^ a b c d e Cite error: The named reference Titford, 2005 was invoked but never defined (see the help page).
  8. ^ a b c Cite error: The named reference Ortiz-Hidalgo and Pina-Oviedo, 2019 was invoked but never defined (see the help page).
  9. ^ a b Cite error: The named reference Ponting, 1973 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference Chan, 2014 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Llewellyn, 2009 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Smith, 2006 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Kiernan, 2006 was invoked but never defined (see the help page).
  14. ^ a b Cite error: The named reference Dapson and Horobin, 2009 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference Titford, 2009 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference Kahr et al., 1998 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference Bettinger and Zimmermann, 1991 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference Dapson et al., 2010 was invoked but never defined (see the help page).