Structure via PubChem · Public domain (PubChem)
hematoxylin
Sign in to saveAlso known as hydroxybrazilin, hydroxybrasilin, cis-(+)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, (6aS,11bR)-7,11b-dihydrobenz[b]indeno[1,2-d]pyran-3,4,6a,9,10(6H)-pentol, (+)-hematoxylin, Haematoxylin
Haematoxylin or hematoxylin (), 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 . 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
Chemical data
- Formula
- C16H14O6
- Molecular weight
- 302.28 g/mol
- IUPAC name
- (6aS,11bR)-7,11b-dihydro-6H-indeno[2,1-c]chromene-3,4,6a,9,10-pentol
- SMILES
- C1C2=CC(=C(C=C2[C@H]3[C@@]1(COC4=C3C=CC(=C4O)O)O)O)O
- InChIKey
- WZUVPPKBWHMQCE-XJKSGUPXSA-N
- XLogP
- 1.2
- Polar surface area
- 110 Ų
- H-bond donors
- 5
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
51,217 papers- Tissue processing and hematoxylin and eosin staining.Methods in molecular biology (Clifton, N.J.) · 2014
- Manual hematoxylin and eosin staining of mouse tissue sections.Cold Spring Harbor protocols · 2014
- The hematoxylin and eosin stain in anatomic pathology-An often-neglected focus of quality assurance in the laboratory.Seminars in diagnostic pathology · 2019
- Oil Red O and Hematoxylin and Eosin Staining for Quantification of Atherosclerosis Burden in Mouse Aorta and Aortic Root.Methods in molecular biology (Clifton, N.J.) · 2015
- Hematoxylin Nuclear Stain Reports Oxidative Stress via Near-Infrared Emission.ACS chemical biology · 2023
via PubMed
Wikidata facts
- Mass
- 302.079038
- Image
- Haematoxylin powder.jpg
Show 5 more facts
- chemical formula
- C₁₆H₁₄O₆
- isomeric SMILES
- C1C2=CC(=C(C=C2[C@H]3[C@@]1(COC4=C3C=CC(=C4O)O)O)O)O
- canonical SMILES
- C1C2=CC(=C(C=C2C3C1(COC4=C3C=CC(=C4O)O)O)O)O
- Commons category
- Haematoxylin
- melting point
- 140
Sources (6)
via Wikidata · CC0
~11 min read
Article
11 sectionsContents
- Extraction and purification
- Use as a histologic stain
- Stain formulations
- Table of significant formulations
- Early use as a histologic stain
- Shortages and possible alternatives
- Use as a textile dye
- Use as a writing and drawing ink
- See also
- Further reading
- References
Haematoxylin or hematoxylin (), 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 . 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.